So you made it past the second date club? Go team, time to roll out the welcome wagon and give yourself a pat on the back. While first dates tend to be quite fancy and you feel the need to impress, the second date is all about showing a ‘glimpse’ of the real you and demonstrating who you are as a person. After all, you are clearly doing something right if they want to go on another date with you. But what on earth do you wear? Well fear not my little pumpkins, Faded Spring has an outfit to suit every ‘second date occasion’ you can think of. From keeping it casual to tapping into your inner Princess, mama’s gonna show you how it’s done.
Last week readers offered advice on what I should wear for my own ‘second date’ at someone’s house and the top two choices were ‘jeans and a nice top’ and ‘ a midi skirt and top’. Naturally being the disorganized person that I am, I ended up changing my ‘casual outfit choice’ which you can see in 10 Dating Terms and went straight back into my ‘comfort zone’, with a beautiful if over-fancy pink ‘Princess dress’. But I had good reason to A. believe it or not ‘princess dresses are what I feel most comfortable in and B. Mirror Mirror users seem to like it best too. That being said while I listen to readers suggestions, ultimately I go with my gut instinct and the Princess dress seemed to do it for me. But I digress, while the second date ended up being ‘fun’ but didn’t lead to a third date, it made me think what I should wear for different ‘second date’ occasions.
What I Wore On My Second Date
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What To Wear For A Second Date At A Fancy Restaurant
So you might have gone to a bar for drinks for your first date and now your second date is taking place at a fancy restaurant and you are scared shitless. What can you wear that will A. be fancy enough, B. be comfortable and C. hide your impending food baby? Well fear not my pretties because I am the ultimate curator when it comes to ‘fancy restaurant wear’. From dresses to jumpsuits, never let a location compromise your personal style. Ultimately wear what makes you feel comfortable but is still dressy enough for a ‘fancy restaurant’
If You Are Into Dresses
So your date has checked you into a fancy resturant in the Shard and you’re feeling nervous, especially when your idea of fancy is Nandos. Nevertheless you want to make a good first impression and have picked out a beautiful dress to set the mood. Word of warning though, if you are a messy eater then stick to darker colours, as any food spilled will show up less than if you are wearing a pristine white dress. I tend to not go for ‘bodycon’ when I am eating as it gets too tight around the stomach when I am eating and I want to be comfortable when I eat. When it comes to choosing a dress, a skater or a-line style ‘dress’ is still fancy but because it is fitted at the top and flared at the bottom, it means it will not tighten around the stomach , leaving you room to eat ( and breathe).
A Perfect ‘Fancy Resturant Outfit’, especially since it has a ‘fitted top half’ and a ‘skater’ bottom half.
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If Jumpsuits Are More Your Thing
We all love a jumpsuit or two and whether your choices are flared, slouchy or fitted, jumpsuits can be the perfect dinner companion. Not only can jumpsuits double up as a great ‘club’ outfit if you choose to take the party elsewhere but choosing a tailored but comfortable jumpsuit will make you feel super relaxed on your date. The key to a fancy resturant ‘jumpsuit’ is to look at the tailoring. I find that a fitted ‘upper silhouette’, with flared 70’s style bottoms still creates the illusion of a ‘great shape’ but allows you to move around easily and more importantly eat.
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With A Sweetheart Neckline and Peekaboo Detailing, The 70’s Style Jumpsuit Is Ideal For Fancy Restaurants
If You Are Going On A Picnic
Picnics are by far one of my favourite date pastimes, especially as it makes me feel nostalgic for my youth. There is nothing more romantic than curling up with your date and tucking into cheese, wine and grapes on a checkered picnic blanket. Question is what do you wear to a picnic? Well dependant on weather, there are a few key choices that ‘scream picnic couture’.
If It’s Winter
God forbid you would want to spend some time outside in the cold but if you do, jeans and a cute top, with a winter coat will still look classy but it will keep you warm too. I find that jeans have often been ‘stereotyped’ as boring but that is certainly not the case, especially if you find a pair of distressed mom jeans and pair with a floaty floral 70’s blouse and a killer floppy hat. Alternatively a pair of embroidered ripped jeans, with a matching embroidered shirt and matching boots, means that you will still be toasty but not look like you are dressed for the Antarctic either.
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Distressed High Waisted Mom Jeans Are ‘Super Comfortable’ And Ideal For ‘Winter Picnic Dates’
If Its Spring
The birds are trilling and the flowers are blooming, the cool breeze with a hint of sun means that spring is here. Having a ‘spring themed picnic’ is quite honestly the best time of year to go, especially when you can ditch the winter coat. But what do you wear? A floaty midi skirt with an off the shoulder top, complete with floral embroidery captures the mood of spring picnic dates perfectly or if skirts are not your jam, some culottes and ankle gladiator sandals should do the trick.
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A Flirty Off The Shoulder Top And A Floaty Midi Skirt Is Ideal For A ‘Spring’ Picnic
If Its Summer
Picnics in the summer are glorious, especially when you crack open the champagne and feed each other strawberries. A summer ‘picnic’ look is quite similar to what you would wear to the beach; whether you choose to wear shorts and sandals or a flirty playsuit, ‘comfortable’ tailoring is key. Kimono’s are a great shout, as they can be paired with pretty much anything.
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Kimono’s And Skorts Are Great For Summer Picnics
If You Are Going To The Beach
Speaking of beaches, what could be more fun than a date on the beach. There are no fancy dresses here, just slouchy beach wear that is perfect for chilling on the beach. From skorts with kimonos to watercolour kimonos and gladiator sandals, remember the key to nailing ‘beach wear’ is comfort and practicality. I tend to go one of two ways; either a kimono cover up with a bikini underneath and gladiator sandals or an off the shoulder midi beach dress complete with a floppy hat. I also wear skorts and vest tops. After all going down the beach, especially on a second date does not mean that you are going to be jumping into the sea anytime soon. That being said since I love to swim I also keep a bikini or a swimsuit on underneath just in case.
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Kimono’s Are The Perfect Beach Cover Up
If You Are Going Clubbing
So you are both party animals and like nothing more than to drink, dance and party the night away. Well no bother, because the hottest bars and clubs in town are waiting your return. Here is the issue; when it comes to choosing a ‘club outfit’ you have to bear in mind whether you will be ‘dancing’ or ‘drinking’ or both. If you are dancing then it can be quite hard to dance in a short bodycon dress, especially when you are conscious of flashing everyone in the room. That being said if it is a skater style dress or a playsuit, that is probably best suited to ‘dancing’ as you will most likely feel more comfortable and less conscious.
Dresses For Drinks
While I can dance in the dress below it is ‘quite short’ which means it might be a little difficult to ‘cut shapes’ and not show the whole world my underwear. Thus when I wear ‘bodycon dresses’ they usually tend to be for when I am drinking at a club and there is little possibility of a dance, as the second date is focused purely on drinks and conversation.
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The Off The Shoulder Detailing Combined With A Bodycon Fit Makes It A Great Dress For Drinks
Dresses To Dance In
As I said a-line and skater style silhouettes tend to be the easiest to ‘dance’ in but if you want to be sexy but not flash your pants, a midi dress with a slit and wrapover top detail will ensure that all eyes on you. The key to nailing the side split dress is to choose a dress where the split goes up ‘mid thigh’ rather than up to your crotch as that is the difference between keeping your underwear intact and showing your date more than they bargained for. Then again I am sure they wont be complaining but you might be!
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The Side Split Makes The Dress Ideal To Dance In
If Shorts Are More Your Thing…
The great thing about shorts are how versatile they are to style but more importantly when it comes to ‘clubs’ they are comfortable and practical. Choosing a ‘club style shorts ‘ may lead you to choose hotpants and while that is great, if you want to dance mini-culottes are great to twirl around in. Choose sequins and metallic shorts to make your outfit look anything but basic.
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Metallic Shorts Are Party Ready And Comfortable To Dance In
If You Are Having A ‘Home Movie Night’ and He’s Cooking You Dinner
As you know, my second date was at the guy I was seeing’s house and he cooked me dinner and made me dessert. Because I panicked I settled on a Princess dress, but if I was to re-do a second date outfit at home, I would settle for something that was a bit more casual but still flirty. A nice blouse and skirt with kitten heels or ballet pumps would still be comfortable or if you want something a bit more casual that is suited to having a home movie- and no I don’t mean porn, get your mind out of the gutter- jeans and a nice bodysuit or bardot top with sandals or boots rather than heels nails casual-glam dressing.
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A Floaty Blouse, Boots and Embroidered Jeans Are The Perfect Home Movie Outfit
If You Are Going To A Museum Or Botanical Garden
Going to a garden or a museum not be the idea of your perfect date, but as a history geek and someone who loves nature, having a stroll through a garden or museum is quite romantic. After all if you find by the second date that you have nothing left to say to each other then at least you have something interesting to look at! Flirty dresses, lace and floral skirts are best suited to a garden stroll, while a museum-especially if you are going to spend a lot of time walking- tends to be a little more casual so a hat, blouse, jeans and boots – substitute for a skirt if you want to look a bit more risque- should do the trick.
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An Embroidered Skirt With Boots Is Perfect For A Museum Visit
So there you have it, Faded Spring’s Guide to nailing ‘Second Date Chic’ has come to an end. While there are plenty more ‘dating scenarios’ and outfits that you can imagine, this was a sample of all the most common second dates you could think of. Want more advice on your ‘second date couture’? Then download ‘Mirror Mirror’ today
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What Would You Wear On Your Second Date And Where Would You Go?
Disclosure
Please note I was compensated for working in collaboration with Mirror Mirror, but all thoughts and opinions are my own.
Picnic, please. That sounds like a great second date for me, assuming my pooch can go. 😉 Great post and ideas.
I don’t remember what I wore during my second date but I think its not too fancy. Lol. Still such an unforgettable date.
Great tips, it/s so important to be comfortable but also dress to impress.
These dresses are gorgeous! I wish I was able to see this before. Can’t remember what I wore during my second date though.
I think you look great in all the outfits although the second dress has to be my favourite. It oozes style and sophistication and is perfect for a nice restaurant.
I love the “movie at home date” outfit on you – really casual. I really like the jumpsuit too, but I just looked and they only have it in L and XL left, boo! 🙁 x
Oh my Ana! You look so stunning in each of these outfits! That dress at the start is my favourite – so pretty!
I was going to say that the kimono and the jumpsuit were really cute, but then you kept going. All of the different outfits here you are just simply stunning. Whether it’s the dress with the slit for dancing or the metallic shorts and faux fur top . . . just wow Ana. Wow! Your second date is one lucky guy!
Love all of these outfits u look stunning in all of them. I like to feel comfortable when I go out on dates with my hubby. I can’t remember what I wore when I went on my second date with him.
this is an interesting set of dating tips Ana… for a guy like me.. i actually don’t mind what my girl is wearing on our first , second or succeeding date but much like girls.. boys also dress to impress so I fully understand that it is more like an integral part in making a date successful
i love all your outfits and you look gorgeous as always
I can’t remember my second date outfits, but I sure remember my first. When I found myself almost 40 and single, I tried online dating (for the shortest of whiles). Every time I put on my black and white shift dress, my daughter always smiled and said “Good luck on your first date. Want me to call you in an hour in case you need to escape?”
You have tons of awesome looks here. Those metallic shorts are hot – you rock them!!
I think wear something that you are comfortable in so you are instantly more confident. Love the outfits, especially the metallic shorts!
The pink dress at the start of the post is definite;y my favourite. Love it!
Seeing all of those different outfits (which all look great) honestly just made me feel lucky to be a guy… Our choice in fashion is so much more limited that it makes it really easy to choose what to wear, haha.
What beautiful dresses! These are all great choices to wear on that big 2nd date!
These are all gorgeous outfits. My favourites are the museum outfit and movies at home outfit.
I’d love to have a picnic date, it’s not something I’ve ever done for a date before!
If I was to dream right now, especially that a very important birthday is coming up soon for me (and not a second date, but I guess the outfits still apply), I would love to wear your fancy restaurant outfit on the day. I really love the dress and how it transforms you into an elegant lady (which I have to admit, on a day to day basis I am not, I only wear jeans and tshirts). But I feel that this outfit can definitely make me feel special on the day. 🙂
Love all these looks. Your wardrobe is just so dreamy 🙂
These are such great outfits! I adore the first one and it is such my style so I love it the most especially those shoes. All the other outfits are cute too. I haven’t been on a date let alone a second so I wouldn’t be of help but if the time came for me this would be so helpful and gives me a guide on outfit choices.
You are so stylish, Ana! I love your taste in clothes as well. I think these are all lovely and perfect for the dates that you’re going to.
Awesome ideas here and once again your outfits are on point
I can’t even choose which of these outfits are my favourite. absolutely flipping adore this post and will be bookmarking it for all my future date outfit ideas! xx
My favorite its the off the shoulder bodycon dress its perfect to wear on a date it also looks sexy and classic at the same time…you’re really stylish you rocked in all the outfits
Gorgeous outfits! You look amazing! I’d total wear a dress, they are definitely my go-to, feel good clothing choice!
Dresses are such an easy go to. I wear dresses almost every single day to work and I definitely wear dresses on dates with my husband!
I enjoyed checking out your outfit. I am not into fashion but I love your stylt.s
I like the second dress the most. But all are great outfits and you look good in them
Stylish dresses here. I love them all. Can’t remember what I wore on my dates. I doubt I was this stylish.
These outfits are all stunning. I think the most important thing is to wear what you’re comfortable in and wear the sort of thing you wear regularly, if you’re typically not a dress wearing girl don’t wear one as you don’t want the guy to be shocked when he stops seeing you in dresses and sees you in jeans and tops all the time x
The dress has to be impressive after all, you don’t want a drop of the impression on the second date. The tips and dresses are amazing. I am surely going to look for these when I go for shopping, just to have in stock!
Some great ideas for outfits here, I really don’t miss arguing with my wardrobe before dates x
I really love your style. My favorite dress its the off the shoulder bodycon dress it looks sexy and classy at the same time. I will surely wear that on a second date
Wow – this is a real go to list for every occasion! Mama has really got our backs!!!
Thanks for sharing!
Leigh at Fashion Du Jour LDN x
You nailed all the style choices for each kind of date. I really like how you dress and these outfits are just perfect for the second date.
You look amazing Ana, you always do. Love the Quiz dress, pretty pastel pink, so chic 🙂 x
I guess it really depends on where you are going on the date. The kind of places I would go on a date, I would be overdressed wearing this.
So many great looks here and though I am out of the dating scene at the moment I’m thinking as i’m newly single again that I may be facing first date dilemma quicker than I think. My favourite is the navy 50’s style dress at the beginning with the large flowers.
All of your outfits are gorgeous!
I particularly like the fur coat 🙂
Dani x
I love these outfits, the first one is my favorite
I had never thought about what to wear on a second date. It looks so amazing to be like you are telling us !
I like the blue dress with the A line skirt. It looks comfortable enough to wear but still very classy. I don ‘t remember what my second date looked like. Haha. Maybe because it was not a memorable one?
I love the looks you’ve picked out, you have every second date scenario covered! x
They all are great outfit! I love the pale blue jumpsuit and the outfit with the faux fur jacket! so so nice! xx corinne
Of all the options you presented, there are two that are my hands-down favorites. 1.) I’d invite you on a picnic just so you could wear the kimono and skort outfit…it looks great. 2.) The silver, off-the-shoulder dress actually made me say “D#**” out loud…anytime that happens, you’re definitely doing something right!
All of these outfits are great, but I’m particularly fond of that beautiful, embroidered floral skirt!
I have a second date today but because of my new tattoo, I can only wear a skirt or shorts, whoops!
Ooh congrats on the second date! I am excited to hear more! xx
Some great ideas and pictures. I think the jumpsuite one!
Great ideas! I agonise over every date outfit, which is ridiculous when he’s known me ages and seen me at my worst! It’s good to put effort on, I love the Dorothy Perkins dress.
All outfits are so pretty and stylish! My favorites are jumpsuit and fancy restaurant outfit x
All of these outfits are really pretty, if I was about to go for a second date having your wardrobe I’d have no idea what to chose! For me the most important thing is to be comfortable as that’s when I feel myself so I’d probably go for something classy, simple and discreet Xx
Well.. if you ask me… I don’t give much attention to what I wear on the first date.. I’m just trying to be as comfortable as possible. As for the place.. I would take my possible gf to a meal.. probably a brunch… or pizza. Dinners are way too official lol.