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
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.
Shop The Ice Skating Faux Fur Coat & Boots Combo Below
Shop Ice Skating ‘Date’ Looks Below
What To Wear On A First Date In Winter…If You Are Going On 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.
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
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.
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
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!
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
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…
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
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.
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.
Shop The Christmas Ball Look Below
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What To Wear On A First Date In Winter… If You Are Going To A Christmas Market
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.
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
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
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
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?
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Please note this is a paid partnership between Nakturnal and Faded Spring but all thoughts and opinions are my own.