Sign up here to be the first to know about everything Song of Style


SOS! I Asked Aimee What I Should Wear On A Date

Hi everyone! This is Sophia from the SOS team. As someone working in fashion, I would say I am pretty good at deciding what to wear. But there’s one occasion that always had me at a loss for ideas… the first date. People always say you dress like your normal self and be comfortable… but in reality, don’t we all try a little bit harder to leave a good first impression?

My problem with dressing for the first date is that I want to wear something flattering, shows my personality, but is not too fashion forward. I try to stick with my usual style but I don’t think a chemical engineer from Tinder would understand why I’m wearing those “ugly” split-toe Tabi boots.

With that said, I always find myself flipping through my whole closet right before the first date to find the “perfect” outfit. As the Valentine’s Day is approaching, I make it my mission to find out what’s the best outfit one should wear to a first date and of course, my first thought is to turn to my very stylish boss and co-workers. So here are what Aimee and the SOS team would wear to a first date:

Aimee: Mixing red and pink

Since I’ve started attending New York Fashion Week, Valentine’s Day always falls in between or towards the end so I haven’t been able to do a proper ‘date night’ but that hasn’t stopped me for dressing up for the Valentine’s day spirit. I love mixing red and pink with a touch of fun accessories.

When I asked Jacopo, he said his ideal date night outfit for me would be an oversized red turtleneck with a pair of denim for a casual look with a red lips or a simple black midi dress (he just loves an all-black look) so I’d probably do a black slip dress with an oversized teddy coat and a pair slouchy black boots.

Her Ideal Outfit:
Sies Marjan Pipa Shearling Peacoat 
Orseund Iris Ruched Satin Dress 
Cinq A Sept Feather-embellished Silk-satin Camisole 
Victoria Beckhem Panelled Flare Trousers 
Grlfrnd Carmen Frayed Mid-rise Straight-leg Jeans
Miista Croc Skin Leather Boots
Chloe Gold Femininities Necklace

Maggie: No such thing as ‘dress to impress’.

To me, there’s no such thing as ‘dress to impress’. If my date doesn’t vibe with my personal style, then there’s no second date.  I don’t like dressing for anybody but myself. My go-to outfit is probably tucking an oversized half-buttoned white dress shirt in my wide-leg suit pants. If I feel extra fancy I would throw on something like this Vince delicate cozy sweater dress, paired with my Maison Margiela Tabi boots (some might say they are man-repelling, but oh well). And there’s no better to carry The Row Ascot Satin Bag than a date. It holds your phone, wallet and your favorite shade of lipstick, nothing more and nothing less.

Her Idea Outfit:
Tibi Twill Tapered Pants 
H&M White Dress Shirt
H&M Hoop Earrings 
COS Mesh Underwired Bra

Patricia: Confidence is all I need

To be honest, I don’t really buy outfits for a date. I usually wear my tried and tested outfit formula and amplify it with extra swipes of lipstick and whips of mascara. There’s nothing like a flattering pair of pants that give me confidence – all I need for a date. If I happen to have a date this Valentine’s day, I would wear my favorite outfit formula: high-waisted wide leg pants paired with a cute top or sweater; topped off with an oversized blazer and a pair of brown boots. To add a little fun to the look, I would reach for some gold jewelry (like this and this) and a cute handbag.

Her Ideal Outfit:
L’AGENCE High-waisted Pants
Brighton Crop Top 
ASOS Oversized Camel Blazer
Frye Leather Western Boots
Simon Miller Bucket Bag
Maison Irem Coin Drop Earrings
Gorjana Quinn Delicate Wrap Necklace

Ruth: Major points if they notice my cool shoes.

For dates, I usually wear my signature outfit: A nice blouse, high-rise jeans and a pair of interesting shoes. I keep my outfit pretty simple because I don’t want to reveal all of me at once. But I always wear a pair of interesting shoes to spice up my outfit! (Major points for your date if they notice my cool shoes.) Personally, I love a pair of nice snakeskin boot or a colored heel. A heel for height purposes + that extra confidence it provides- never hurt anybody!) But honestly wear what you feel best and confident in (whether that be your much loved in sneakers or that kimono that never fails to get you noticed). Keep it light and interesting and HAVE FUN.

Her Ideal Outfit:
Matisse Frame Sandal 
Topshop Hurricane Bootie
Topshop Jessica Print Shirt 
Topshop Satin Cowl Neck Camisole
Madewell Coin Necklace

Recommended for you


8 months ago

15 Best Blazers and How I Styled Them

When in doubt, wear blazer jackets. They are the most versatile jacket for fall, or any season really. I wear them with midi dress...


7 months ago

My Favorite Designer Bags Are On Sale Now

All retailers like Net-a-Porter, Matchesfashion and SSENSE are having their biggest end-of-season sales. This is the perfect time ...


3 months ago

Sweatpants But Make it Fashion

Almost 4 weeks of quarantine has furloughed everyone’s closet. Sweatshirts and sweatpants are receiving more love than ever ...

Recommended for you