Knowing What To Wear On A First Date In Winter, can be a tricky feat to master. After all, is it just me who has a strong urge to shut out the world and pretend that the outside just doesn’t exist? Or maybe its just me who wishes she didn’t have to shave her legs every 5 seconds and would rather come dressed as a giant blanket instead. Nope just me. When it comes to ‘getting past the first or second date club‘ i’m under no illusions that I have the advice to take you from single to married in 10 minutes, so I would rather share some tips with you that I can actually talk good shit about and that is fashion. While turning up in a breathtaking £1,000 Ellie Saab dress might not be the best idea for a first date in winter, it doesn’t mean that you have to ransack your wardrobe and put on every jumper that you own either. After all, I would prefer it if you could actually move your arms and not take 5 hours to peel off all your layers after intense and romantic snowball fights.
After five months wandering as lonely as a cloud- I jest- I finally managed to get a Tinder date, but what on earth would I wear? Well me being me, I ended up looking like a massive 80’s glitter ball, dressed in sequins of course and that was just me getting ready to eat my weight in food at an Indian Restaurant called Woodlands in Marylebone. Luckily my good ol alter ego Jasmine likes to tell me how ‘sensible she is’ read – wild- and suggested that she would take the reins from here and tell you my readers what you should wear on a first date in winter for all the possible occasions. From First Dates at Winter Wonderland sipping mulled wine and pushing children out of the line so you can ride a magic polar bear , to First Dates on ‘Santa’s knee’ when it comes to making sure your wardrobe fits the Christmas theme my post will turn you into a magical sparkling unicorn who will dazzle her first date. And if he doesn’t like sequins… well he will just have to fuck off.
Let The Winter Dating Games Commence…
What To Wear On A First Date In Winter…If You Are Going Ice Skating
A Faux Fur Coat, Embroidered Jeans and Socks Boot Combo Looks Just As Flattering On The Ice Rink As It Does Off The Rink Too
The last time that I went ice skating was when I was seven years old and I remember wearing a purple velvet dress, while I attempted to do something fancy and do some ‘tricks on the ice’. Unsurprisingly I landed flat on my face and scraped my knee until it was quite literally turning the ice red. It sounds like something out of a horror movie- girl wears dress… girl bleeds to death on ice- but truth is the ice skating rink can be a vicious and competitive place for a beginner like me, who knows zero about ice skating. Although I have not been ice skating since I was seven years old, it does not mean that I wouldn’t want to again, its just that the opportunity has never presented itself. Which is why I thought it would either be a ‘romantic date’ with a potential love interest or a hilarious evening laughing at each other because you both look like sausage dogs on ice. But what on earth does ‘sausage dogs’ and ‘ice skating injuries have to do with fashion I hear you ask?
Well sausage dogs are cute and ice skating injuries are horrendous but question is what should you wear on a first date if you are going ice skating in winter? Well A. its going to be super nippy and B. you still need to look all sorts of fabulous, so merging the line between cozy and turning up in a fluffy blanket is a tricky medium to convey but thanks to Jasmine, she’s got your back boo. When its minus 5 degrees and your feet are frozen as f**k, chances are turning up in a cute dress just isn’t going to cut the mustard, so why not get yourself a stylish jumpsuit and boots combo or even better still slim fit jeans with a jumper, a faux fur coat and a batwing jumper to dazzle, even when you don’t have a clue as to what you are doing on the ice. Chances are your partner will be so dazzled by your stylish OTTD, that your horrible attempt at twirling and flipping on the ice, will be a distant memory for both of you.
Turning Up The Heat With A Faux Fur Coat. Sunglasses Optional…
Shop The Ice Skating Faux Fur Coat & Boots Combo Below
*Affiliate Links
Shop Ice Skating ‘Date’ Looks Below
What To Wear On A First Date In Winter…If You Are Going On A Hot Chocolate Date
The Rust & Burgundy Combo Is Aesthetically Appealing But A Jumper & Mini Skirt With A Cocoon Coat Is Ideal For A Hot Chocolate Date
If you aren’t quite ready for a ‘dinner date’ and would rather a less formal introduction to your future husband, then what could be less pressurizing than a hot chocolate date in winter? Perfect for beating those winter blues and getting your sugar fix, so even if your date turns out to be a complete douche at least you didn’t have to spend too much money on him or drag your dusty sequin maxi out of hiding, so that you’d look like a complete and utter twat at Costa. Whether you choose an independent coffee shop or the Starbucks Crew know your name off by heart, this casual non formal date will make both of your tummies happy. After all ’tis the season to drink and eat’ so you might as well drag your beau along with you. And who knows, maybe the hot chocolate date could transform into something more romantic like a walk around the Christmas Markets where you steal everyone’s mulled wine? Sounds pretty magical to me!
But the problem is what do you wear if you are going to be drinking hot chocolate with your latest Tinder match? Easy! A Turtleneck and Mini Skirt combo is not only a fail safe 60’s Casual Cult Classic but it also makes a pretty good choice for your hot chocolate date with your crush. For starters the fishnet tights add sex appeal, but the cocoon coat and jumper help keep you warm and allows your outfit to not be too try hard, while the faux leather skirt is complemented by the studded ankle booties. If skirts are not your thing and you would rather turn up with a bag over your head then wear fishnet tights then no worries chicas because Mama Jasmine has some cute ASF casual tea dresses, Fun denim and Patterned tights to make you sparkle, even if your date doesn’t.
Keeping It Fire In A Cozy Cocoon Coat. Ideal For Hot Chocolate Dates In Winter
Shop The Faux Leather Mini Skirt & Cocoon Coat Combo Below
Shop Hot Chocolate Date Picks Below
What To Wear On A First Date In Winter…If You Are Going To See Santa
Oh Hey Santa It’s Me… Any Chance You Can Make This Date A Success And Reinstate Me On Your ‘Nice List’
Santa’s giving his list a once over and it seems like your name is not on the list! Looks like someone has been struck off the list and you have no idea why? Maybe Santa knows that you ate all the mince pies last Christmas or that he gave you fabulous presents to give to other people, which you kept for yourself. Either way it looks like you have some explaining to do and what better way to make a first date even more awkward than through a visit to Santa? After all even if your first date is a total misfire and he doesn’t get your sense of humor, at least Santa can reward you with putting your name back on his nice list! So whether you have been naughty or nice or trying to get back in Santa’s good books, nothing screams Christmas more than a visit to Santa and his elves. Although to be fair Santa might get a little confused at the two fully grown adults pushing all the children out of the queue but hey ho that’s show business for you.
So if you need to get Santa (and your date’s) attention but don’t want to be rocking every Christmas Cliche going, then a simple blouse and mini skirt combo, with this seasons hottest footwear aka the trusty sock boot, will be enough to suffice. And bonus points for outfits that use contrasting colours like pumpkin and burgundy or rust and pink? You know how much Mama Jasmine loves those matching outfits. But if you would rather show up dressed in every festive cliche known to mankind then don’t worry, I got you some ugly Christmas Jumpers too. Besides if your first date would rather not see Santa, at least you can send him packing with your ‘ugly-cute’ Christmas jumper. Ahh Christmas Jumpers, warding off dating disasters since 2000 BC.
A Blouse Is Perfect For Seeing Santa In Winter
Shop The Blouse & Skirt Combo Below
Shop The ‘Seeing Santa Date’ Picks Below
What To Wear On A First Date In Winter…If You Are Going To Winter Wonderland
Adding Some Colour To The Winter Wonderland Festivities
Ah Winter Wonderland. There is nothing better than pretending you are a big kid at Christmas and canoodling on the rides with your future bae. Or if public displays of affection are not really your thing, then lauding the fact that you are over 18 by boasting about mulled wine in front of jealous children sounds just as fun! My personal favourite is pretending to be the ‘Grinch’ and laughing at the children who are not tall enough to get on the rides… ah the sweet bliss of not being a child anymore. Of course I’m joking I actually love children and don’t go around throwing mulled wine in their faces or pushing them out of lines…
But what screams Winter Wonderland on a first date? While its easy to go super cheesy and come out dressed as one of Santa’s Elves, its not Christmas Day yet and besides you don’t want to look like you are auditioning for The Nightmare Before Christmas do you? So why not leave the cringeville to Santa and his pets and wear a warm yet stylish co-ord combo that is guaranteed to turn heads. While knee high boots might not be the comfiest choice, they are great for making an entrance, while a trench coat, whether it be faux suede or faux fur is perfect will keep you warm, even if the outfit underneath is skimpy. My top tip, wear nude tights if you are going to venture into skirt territory in the middle of winter, because its pretty cold out there and I don’t want you catching pneumonia. If co-ords remind you of baby dungarees then not to worry, some pearl embroidered jeans, duster jackets and ruffle long sleeved blouses will capture the Winter Wonderland spirit too!
These Burgundy Over The Knee Boots Will Slay Your Date
Shop The Co Ord Look Below
Shop The Winter Wonderland Date Picks Below
What To Wear On A First Date In Winter…If You Are Going To A Christmas Party
Sequin Brocade Dresses Have Just Enough Glitz And Glamour For A Christmas Party Date
So your crush has invited you to his Christmas Work Party but one quick look at your wardrobe and you realize that a moth eaten jumper will not suffice. Don’t worry Beatrice, from Sequin Dresses fit for a part time Mermaid, to unicorn inspired haute couture wear, when it comes to Christmas Parties Mama Jasmine never disappoints. While sequin dresses almost seems like a prerequisite for ‘Christmas Parties’ you don’t necessarily have to wear sequins to get in the Christmassy mood. From velvet, to brocade, right through to themed dress up looks, one thing is for certain, even if you and your chosen date don’t click and he ends up with his tongue down Deidre’s throat, at least you can dazzle some of his work colleagues with your less than fabulous dance moves.
Hey noone can blame a trier after all and besides what better way to liven up a dating disaster than with a dance ready outfit that will trick your peers into thinking your dancing is out of this world. They will be so entranced by all the sparkles and shimmer that the memory of you being inebriated and trying to dance with the broom, who at the time you think is your dance partner, will be nothing more than a drunken day dream. And if all else fails stick your dates head in the punch, steal all the mince pies and tell Santa you are on your way…
Add Some Sunglasses To Blind All The Haters
Shop The Sequin Dress Look Below
Shop Christmas Party Looks Below
What To Wear On A First Date In Winter… If You Are Going To A Christmas Ball
Feel Like A Princess On Your Special Day… I mean First Date!
Hubble Bubble Toil And Trouble… hang on that’s the wrong song, its Christmas not Halloween! Now that fall is well and truly over, chances are that you will be invited to a fair few Christmas Balls and what better way to get to know a potential Tinder Match, then through a Christmas Ball, where you can look like a bridesmaid or worst still a bride on your first date. Hey if you wanted to ask someone for ‘casual date wear tips’ then sorry mate, I don’t think that I am the right choice. But if you’re after a wowzer of an outfit that is guaranteed to stop you from being friendzoned, then hello Mama Jasmine is here to save the day.
Pink To Make The Boys Wink 😉
Imagine ‘Santa Baby’ wafting over the speakers, as you twirl and dance until you are quite literally ready to drop. But while a Christmas Party demands all things tacky and sparkly, a Christmas Ball is more of a demure and elegant affair. From chiffon brocade maxi dresses plucked out of the imagination of the Snow Lake Ballet, to satin concoctions made of candy floss and all things sugar and spice, when it comes to Christmas Balls it seems that sickly sweet is the order of the day. But if the sight of pink makes you want to cry, don’t worry hun’s there are plenty of alternative wardrobe options to make even the fussiest girl happy. If blue is more of your cup of tea and lace is your type of ‘winter spice’ then fear not Cari’s Closet , has your Christmas Ball needs sorted. From blue lace concoctions that will make you look like Elsa from Frozen to sequin maxi dresses that will have you red carpet ready, your Christmas Ball has never been so glamorous.
Original Dress From Cari’s Closet
Shop The Christmas Ball Look Below
Shop Christmas Ball Date Looks Below
What To Wear On A First Date In Winter… If You Are Going To A Christmas Market
Create A ‘Casual Sequin’ Look For A Christmas Market Date With A Shift Sequin Dress & Layer Over Fishnet Tights & Team With A Faux Fur Bolero
There is nothing better then wandering around Southbank or Borough Market as you feed each other pieces of cake and drink from the same cup of mulled wine. The lights are twinkling in the background and the sound of Christmas music which would normally piss you right off, has got you feeling merry for some strange reason. Although to be fair treating yourself to 10 cups of mulled wine probably has something to do with that, but shhh don’t tell your date. Even when you see him scratching his head as he wonders where on earth his mulled wine disappeared to, its probably best to keep quiet.
But mulled wine stealing aside, find out whether your new Tinder Match has the powers to become your ‘Instagram Husband’ with a cheesy photoshoot, featuring reindeers, a photobombing Father Christmas and some good ol’fashioned Christmas cheer. Chances are you will know if he or she is a keeper because if they are able to grimace their way through your horrendous rendition of ‘ Silent Night’ which sounds more like the Silence of The Lambs, than a Christmas Sing A Long. And if they can pretend to like your ‘fantastic singing’ then chances are they will forgive your mulled wine stealing habits too! But what could be cozy enough with the right amount of sauciness to heat up your Christmas Market snoop session I hear you ask? Enter my failed attempt at a casual sequin look; team a sequin slip 90’s style dress with fishnet tights and over the knee boots, while a faux fur bolero, lace choker and black floppy hat lends some sass appeal to the otherwise Christmas themed look.
If sequins-even dark Gothic glorious sequins like the ones below make you want to go dressed as a blanket instead, don’t fret pet, from velvet playsuits or rompers as you call them in the US, to cozy jumpers that will snatch your edges and have you singing to church and back don’t worry gurl I got you! Or if a Barbie pink assemble to make the boys wink is your idea of Christmas Market Fun, then hop on board the festive train mobile.
Sequins & Fishnets- What’s Not To Love?
Shop The Attempt At A Casual Sequin Look Below
Shop The Barbie Pink To Make The Boys Wink Look Below
*Original Duster Coat From Tobi
Looks More Satin In Person
Shop Christmas Market Date Looks Below
What To Wear On A First Date In Winter… If You Are Having A Christmas ‘Netflix And Chill’ Session
A Cozy Jumper & Matching Boots Will Be A Perfect Choice For Netflix & Chill. Bonus Points If There House Is Covered In Street Art
Now i’m not a personal fan of ‘Netflix and Chill’ because while it might actually mean watching movies and cuddling to me, it seems like your date often has other plans. But let’s presume you manage to catch a gentlemen on POF who wants nothing more than a Shrek Movie Marathon, while feeding you chocolate cake- can we find this man? Where is he hiding? What on earth can you wear that doesn’t involve you turning up in a bridesmaid dress because you’re too stressed to find something casual- Oh wait, I did that on a second date with a doctor. Safe to say he did not want to see me again… But I digress, while I should have consulted with my trusty handbook on what to wear on a second date, a Netflix and Chill session, deserves comfort and style, without looking too try hard. Although in all fairness I am probably the ‘least casual’ person you could ask for first date wardrobe advice but hey ho I’m pretty sure you have realized your mistake now!
From warm cozy knit jumpers in a glorious shade of duck egg blue to colourful boots, that at the very least can help you run away in style if your date turns out to be a snooze fest, Netflix and Chill has never looked so ‘warm’. Although come to think of it, most Netflix and Chill sessions end up in a cheeky romp, so you might want to pack some fancy underwear too just in case.
Original Boots From Koi Footwear
Oh Hey There Turtleneck Jumper… Slaying Since 1939
Shop The Jumper & Skirt Combo Below
Shop The Blouse & Fishnets Combo Below
* Original Blouse From Tobi
Shop The Netflix & Chill Date Looks Below
What To Wear On A First Date In Winter… If You Are Going To The Theatre
A Modern Version Of Audrey Hepburn’s 50’s Midi Dress : Perfect For A Winter Date At The Theatre
Nothing tells me it is Christmas Season more than a trip to the theatre; from the ages of 10 up until I was 17, I used to go to the theatre with the whole South West Foster Carers & Children Community and we watched everything from Wicked right through to my first West End Musical The Lion King, which remains my favourite musical to this day. But imagine how ace a first date to a theatre in winter would be, especially during the Christmas season! I remember taking my friend to see The Book of Mormon in January and it was one of the best musicals that I had ever seen, so imagine being in fits of giggles with your future partner in crime? Besides at least if you are finding it awkward and have no sparks with your date, the theatre trip will mean that it hasn’t been a wasted trip. But if you can feel your heart beating a little louder, every time that he leans over to grab some sweets, imagine how much you will be rewarded with a stolen make out session, once outside. But remember, classy not brassy.
Theater’s don’t have a specific dress code per say, but being the overdressed person that I am, I say go hard or go home! Whether it is midi dresses from my all time favourite Chi Chi London or plunge neck jumpsuits, put the glitz and glamour back into theatre.
Shop The Audrey Hepburn Midi Dress Look Below
Shop The Winter Theatre Date Pieces Below
What Would You Wear On A First Date In Winter?
P.S I managed to snag you some much needed discounts for all you lovebirds out there so be the early bird that catches the worm. I promise you its worth it.
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*Disclaimer
Please note this is a paid partnership between Nakturnal and Faded Spring but all thoughts and opinions are my own.
These are all great looks and you look amazing. I have to say that I love the faux fur coat the most. It is adorable.
love the colours that you’ve chosen, really pretty. My favourite is the theatre dress I think (probably because I’d love to go to the theatre too)! ha x
OMG I am totally the girl who tries to hid away and read a book in the winter! But it’s so good to get out and dressing well for a date is always a good start. I love your skating outfit! Your Christmas Market is amazing, those boots!
I love all of these looks! Those red/rust shades look great on you, and I adore that blue outfit too.
I think it’s really tricky, personally I never now what to wear on winter but I’m in love with your choices! Favorites here Faux Fur Coat and the boots from Pretty Little Thing! Ordering a pair now!!
You can never go wrong with the turtleneck sweater! It’s versatile and comfortable. I like how your outfits make the date.
Some fab items here!! I’m loving the Bordeaux red options, perfect for the season. The blues are really fun and playing and the peachy blush items add that element of elegance. Love how you styled these looks!
I like your ideas. All of them are pretty! I’d probably show up in jeans and a sweater since I’m all about comfort. If a dude doesn’t like me for me, peace out.
Gosh it has been ages since I even had to think about what to wear on a first date, it is always so hard to think about the right thing to wear and the impression you want to give off.
Great tips on what to wear on that first date. My wife and I have been married over 22 years, so, first dates have already happened 😃
I love these looks that you create. do you book a professional photographer? The lighting is just right. I also like the shade of lipstick – very cool 🙂
Thank you that is very kind! I take some of my photos if they are photos of products/ food/ event reviews but I do have a professional photographer for my fashion shoots 🙂 thank you its NYX and its a greyish brown which is a different lipstick colour for me. Always good to be different!
Stunning outfits Ana I love the blue jumper id wear that and team it with a good pair of jeans as I’m all about comfort.
The reds a great too I do love burgundy this time of year.
Love the pink fur coat!
love all these outfit looks but I am totally glad to be out of the dating scene. but these are still great for just a holiday party with the hubs.
I love big, warm coats in winter and the faux fur coat is gorgeous! You look great in all of the looks though
I love big warm coats like this over those really cold winter months! Not only do they look warm but they are gorgeous!
These are all amazing outfits. I am in love with the maroon boots. They would be a great addition to my wardrobe.
I’d love to go on a hot chocolate date! Love the colour of your jacket in that one.
all of your outfit selection are just WOW. I am definitely inlove with the baby blue color and all other bright colors. The dresses are so chic and sleek. Thank you for sharing.
I love each of the looks that you have shared! They’re all perfect for the specific dates, for sure! My fave outfit would be the one for ice skating!
Great options especially winter is so brutal with outfits and being stylish. I love your pink choices 🙂
Oh wow these are some amazing outfits! I won’t be going on any first dates anytime soon, but I would iove these!
Wow these are some really nice styles here. The color combinations and textures are great. I have so many favorites. I like the blue sweater you paired with the slightly paler blue skirt, and the black sequined dress with the black knee high boots.
Holy Moly Lady!! Wowowow!!! These looks are incredible! In these outfits you will only need one because the guy is going to fall head over heels.
These outfits are so stunning. I have a niece who LOVES to shop fabulous clothes. I’ll let her know about these great stuff!
Wow! Your post is sooo sooo in depth! I love all the selections! Fur coats are so popular this season and so is burgundy! I also love the pleats! So much goodness in one post!
Omg. Ok so winter wonderland. Christmas market, and Netflix and chill are my favorite looks. And your fur faux coat in the ice skating look is great too. I want to go shopping now. You did such a good job styling yourself for each occasion. I’m going to go check out some of these links now. I’m literally obsessed with the Christmas market look!
The winter ball outfit is my favorite. That pink gown is gorgeous. I also love all of the suede pieces here!
http://www.therookiewife.com
Such a great post – I’m really loving your knack for accessorising.
C x
I am loving the outfit for Ice Skating, it’s definitely more my style compared to the others. It looks so nice and warm too without having to add 500 layers. You look gorgeous in all of the outfits though, especially love the dress for a Christmas Ball xx
All these outfits look incredible but you in that burgandy outfit look incredible! The colours really suit you
It can be quite tough in winter as it can be too cold to dress up too much, although I am not very much a dress wearer so it’s not too bad for me x
yess im in love with train driver style hats at the moment! cant get enough of wearing mine!
Ana, you have the most amazing style, seriously. You are a natural “clothes horse”. I read through your post and wanted to choose my favourite outfit, but that was impossible, they were all so pretty. However, if I was going to choose just one, it would be the awesome matching blue boots and jumper! Love your little snippets of advice, too – it’s been a long time since I went on a first date!
These are some really bold outfits and they work so well! I haven’t been on a first date in years, but I did go on a date with my partner a few weeks ago to a country pub. I didn’t ditch the jumper though and decided to dress it up a bit with some heeled boots and jewellery.
You are super cute! I was thinking that I will need to come over and borrow some of those lovely pieces, but then, you made it so convenient to get my very own! Love the style, colors and look of your selections. Well done! <3
These are all such great looks! I love the faux fur jacket and the red suede boots, perfect for winter!!
I like the fluffy coat, that would be perfect for winter.
I love the fuzzy coat! I’m taken so no more first dates for me, but these are also great ideas for date night with the hubby.
I love your outfit choices which look super cute and cosy too, my favourite is that fluffy faux fur coat – great price too.
These are some great styles and sure to impress anyone on a first date!
I’m seriously in love with your style! You did such a great job explaining and showing everything! Love the photos!
I love all the styles but I especially love the furry coat! It is so cute!
It has almost been 20 years since I have had a first date and that was in summer! I really like the patterned tights though.
Fantastic set of looks you have here! The fur coat is my fave!
Definitely that Xmas ball dress, omg, it looks so amazing 🙂 And the flower crown is quite cool too! X
Some great ideas for outfits and love the pastel blue on you. Its such a Winter Wonderland type colour!
Fantastic style tips! If I was going ice skating on a date I think I’d need elbow pads, knee pads and maybe one of those inflatable sumo suits… maybe not the best look 😀
Girl! Where are you getting all these gorgeous boots from? I am loving the collection listed here. That faux fur coat and the sky blue sweater is super cute.
These are all great choices and looks lovely! I definitely love the pink princess dress, too cute!
Those ripped jeans are super cute with the faux fur coat! The boots really tie the whole outfit together!
These all look amazing, Especially love the cacoon coat!
So many lovely winter outfit ideas. I love the midi dress for a date at the theatre. Gorgeous dress!
I love that princess dress, its adorable. My partner and I had our first date in November and he told me to dress for walking through a field haha. So I ended up trying to not dress too casual whilst not wanting to get nice clothes muddy and wearing wellies. We walked through some fields along the river to the next village for a pub lunch x
Okay these are all amazing date outfit ideas but all your Public Desire shoes are what stands out for me! I love and want them all! xo, Suzanne
I really love your faux fur. I am almost ready to start dating again which means I need to get my date nights looks together. Thanks for the push.
Cool clothes. I can’t really wear alot of that Momming’ but I’m sure someone could pull it off. Looking fabulous .
I love those boots, they are killer. The entire outfit really rocks!
I love ALL of these. I would totally wear them on a first date in wintertime. I especially love how you rock the hats with your hair. It is splendid!
I like all the outfits, but the pink midi dress is my favorite!
Cute outfits! You have some amazing shoes. For me I live in Texas so we don’t get a huge winter…maybe 40 degrees but still sun bright lol My cold weather outfit is normally just putting tights under my dresses and wearing boots.
Wow! Great combinations – almost every match is a first for me, but pair that catches my eyes and heart the most is the blue jumper with its lovely boots. The pink dress that makes e feel like a princess is interesting too.
Long jeans are a must for ice skating! and that blue knitted jumper like you say is perfect for a night on the sofa having a snuggle and watching a film. Some lovely ideas and styles
For a winter date you need to be warmly dressed yet look gorgeous. You have chosen such beautiful outfits. I love that light blue outfit.
You always look so glamorous! Love the burgundy colour and a fab fur coat to glam things up in winter 🙂
Love all these looks, Ana, this is such a wonderful source for anyone struggling with outfit ideas for their first winter date. I must appreciate how you’ve come up with so many real-life date location-related ideas to help the lovebirds out there!
These are all such fun looks and would work for just about any date night fun! I love the burgundy look because well – that hat! 😀
Gorgeous as always! My husband and I went out on our first date outside the house in almost 10 years a couple weeks ago. Hopefully we can go again soon so I can dress up nice and fancy! You look GREAT!
Your Christmas market outfit is my favourite Ana, I love all the sparkles! And like you said, if he’s not into sequins, then I’m not into him haha 😉 x
The burgundy faux leather skirt is just gorgeous. If I had a figure like yours I would DEFINITELY be picking one up 🙂
Louise x
First dates make or break the relationship. Really great tips, hun!
These are great looks! So glad I am no longer on the dating scene. I find it hard enough to choose what to wear on a daily basis, it would so hard to try to decide what to wear on a date. When I was still dating I would change so many times before leaving the house, making it harder not to be nervous.
Oh my goodness those cranberry knee high boots are DIVINE!! So many good looks here 🙂
You look so gorgeous in your outfits. and the best look for me is Sequin Brocade Dress and Pink long dress. You had an amazing pick of clothes.
Lol “sausage dogs on ice”… I laughed way too hard at that! I am always having this battle in my head of what to wear, but all of your ideas are super fabulous that I will have to keep in mind! I especially love the hot cocoa date look!
All of these selections are a great choice for a first date. I am currently at work talking about date attire and some of the stories i’ve heard today is so funny, in a good way, but passing over to the girls this post.
OMG! You are so creative it kills me! First of all you look beautiful in each look! Second- where in the world did you come up with these perfect dates too!! I meannnnnn going to the Christmas Market! Going to see Santa! Going to a Christmas ball! WTF! I need all these dates to happen to me ASAP – like now – like today!! Lol my favorite look though is your “Netflix and Chill” look! That all blue combo with those boots! I can’t with you and your perfection! This post was major fab-u-licious!!
You are adorable and I’m loving all these outfits. I’d be a big hot mess trying to date at this point. First dates sound horrendous but I met my husband on a blind date 15 years ago – which is very much now like finding a match through an online app. I’m not sure “blind dates” even exist the same way anymore but pretty much every first date without meeting in person beforehand would be a blind date, right? Your posts are the most fun to read!
All the outfits are beautiful and it suits the occasion too..lovely clicks loved them all.. Thanks for sharing
I love all of these! And the places you take pictures are so cool. And no, it’s not just you lol! Even in the summer I’ve been known to go a week without shaving!
I love the Sequin Brocade combo. It’s one of the best I have seen so far. My gf would love it!
I was really drawn to your set, especially I’m loving the Bordeaux red options, perfect for the season. It would be great if I could wear it for the upcoming Christmas season. 🙂
Love your style!! 🙂
Loving the whole burgundy combo with fishnets!It’s sexy, warm and bold for any date night.
These are all great looks but my favorites are the outfit to meet Santa, and the Hot chocolate outfit.
You have a fun sense of fashion. I personally like the sequin look makes me feel the holiday spirit more.
such a helpful post!
Wow! You have great style! I am married for 5 years now so for me first date is over long ago. But these outfits are so cool, I would love to wear them in some other occasions. You have a great collection of shoes!
I swear while reading this post I kept thinking ok, this is my favourite outfit and then I got to the next one and was like no, this one is… And like this the whole way up until the end. Beautiful choices, and I might steal some ideas for date night 🙂
You have such an amazing style. I love that maroon leather skirt, so cute and versatile.
I haven’t thought about ice skating in forever! When I was a kid, my best friend (a boy named Lloyd) and I used to skate on the creek near our house. Such great memories. I can still remember wearing my favorite sweater, big puffy jacket, flannel scarf and red pom-pom hat. I don’t know which I loved more, the ice skating or the hot chocolate his mom always made for us after. xx ( ps: I bet you were the most beautiful ’80’s glitter ball there ever was. ✨🤦♀️ )
Oh my goodness – all of these outfits are seriously fabulous! I don’t think I’ll be going on any winter dates but it’s deffo given me some style inspiration.
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aw cute outfit pica, love all of them :))
I could have done with reading this 7 years ago on my first date with Gaz!! It was November and unbearably cold and I had no clue what to wear in the winter! I ended up wearing a sleeveless dress with no tights and absolutely FROZE to death! Luckily he kept me warm….maybe that was where I went right!!
This is such a great post! It is hard enough figuring out what to wear in the winter, especially if you have a date planned. I love the hot chocolate outing look. You have amazing style and this post is very helpful
That burgundy jacket and hat looks really nice. 😀 I never really thought of what to wear for dating in winter because we don’t have that. I guess it should really be a big deal, huh?
Wow. I love all your fashion tips. Perhaps I will just wear these on a regular date since I am way past the first one. Beautiful choices.
Fabulous pictures.Going on a date during winter, is super nice!
you have such goreous outfits! Very fashionable lady