My first-date track record is hit-or-miss, but I chalk that up to chemistry and not what I wear (thank you very much). When I’m picking out what to wear on a first date, I’m a creature of habit. Having spent a few years navigating dates with strangers, I’ve made a habit of deliberately dressing “normal,” which for me usually entails jeans with a pretty top and a pair of comfortable shoes. Despite what that description may lead you to believe, that’s not to say I don’t put in the effort. As a distinctively low-key person, I’ve realized that I want a first impression to be an honest representation of who I am.
Still, since dating is a process that’s a bit of a closed feedback loop (it’s rare and frankly weird to get a review afterward), I was curious to know how other women dress for a first date. So I decided to ask single friends on social media about their date-night dressing habits. I hope that crowdsourcing other people’s tricks for a first date will make things that much easier for you the next time it’s your turn. Read on to learn more.
An “Interesting” Basic Top + Trousers + Layered Jewelry
Comfort is my top priority when getting dressed for a first date. If I feel good about what I’m wearing, I know that my attention will be 100%, and I won’t be distracted by the need to adjust my clothes during the date. Recently, my favorite combination has been a simple top with a hint of trendiness (think a sweetheart or asymmetric neckline) paired with some relaxed trousers, which are my top wardrobe classic. I usually finish it off with a few fun jewelry items that can act as conversation starters.
Reformation
Cello One-Shoulder Knit Top
$78
The kind of top I’d buy for date night but also wear for everything else.
Topshop
Low Slug Slouchy Pants
$72
Every closet needs a pair like these.
Petit Moments
Rainbow Freshwater Pearl Necklace
$50
Trendy and actually really wearable.
Flirty Top + Leather Pants + Platform Boots
“I like to show my personal style on a first date while keeping it fun and flirty. My go-to outfit formula in the winter is leather pants, platform Dr. Martens, and a cute top that shows some skin (but not too much). Accessorizing is the key to keeping the outfit true to my style. I always wear bright red lipstick, a standout piece of jewelry—either a gold necklace or statement earrings—and a mini purse to keep the look sophisticated and feminine. Lastly, I like to wear a bright-colored coat for a fun pop of color to complete the outfit.” — Emma Greis
Interior
The Vera Top
$580$174
A pretty find.
Coach
Tabby Shoulder Bag
$350
Every fashion person’s go-to shoulder bag.
Mango
Mid-Rise Leather Effect Trousers
$90
Faux-leather pants that only look expensive.
Statement Top + Flattering Jeans + Heels
“My go-to outfit for a first date is extremely simple, and there’s a science behind it. Being stressed out trying to put a sophisticated outfit together before heading out for the night is not going to help you radiate your best energy when you arrive. I always tell my friends that their date is only going to see them from the waist up for the majority of the time, so just focus on finding tops that flatter your figure without being too revealing. That’s why I always choose a statement top and flattering jeans, gravitating toward pairs that make my legs longer. Oh, and high heels are a must no matter how tall he is.” — Sierra Mayhew
Jaded London
Checked Shirt Corset
$59
When it comes to statement tops, this one is supreme.
Madewell
The Perfect Vintage Raw Hem High Waist Crop Wide Leg Jeans
$128
There’s a reason these jeans have the cult following that they do.
Jeffrey Campbell
Caviar Platform Slide Sandal
$140
WWW readers are especially keen on these cute mules.
All-Black Staples
“My go-to first-date outfit is always casual but chic. I lean toward an all-black ensemble because I feel the most confident and comfortable. A little bit of leather never hurts.” — Isabel Campbell
AllSaints
Balfern Leather Biker Jacket
$529
I love the boxy fit of this jacket.
Nordstrom
Relaxed Fit Pima Cotton Crewneck T-Shirt
$40
An A+ basic.
Reformation
Mason High Waist Wide Leg Pants
$178
Everyone’s favorite pants.
Oversize Shirt + Tights + Knee-High Boots + Blazer
“I reach for an oversize shirt or a dress with tights and finish it with knee-high boots and a classic blazer.” — Kelly Reed
Shop the look:
Open Edit
Relaxed Fit Blazer
$80
It’s not every day I call a blazer pretty.
Nordstrom
Long Sleeve High-Low Shirtdress
$90
How to go from the office to a date.
Oroblu
V-Slim Zero Sheer Tights
$35
There’s never a bad time to stock up on these.
Leather Jacket + Fitted Top + Printed Pants
I’ve worn a version of this outfit more times than I can remember on a first date, and it’s never failed to make me feel like the coolest version of myself. I like to add personality to the jeans-and-a-cool-top formula by opting for a pair of checkered jeans. I like that they let my personality shine through and usually earn me a compliment.
Mango
Leather Bomber Jacket
$130
A moto jacket makes me feel cool AF.
Madewell
Sheer Long Sleeve T-Shirt
$42
This top was made for wearing with jeans on a night out.
L’Academie
The Rosie Pant
$218
Meet your new favorite striped pants.
Jeans + Off-the-Shoulder Top
“My perfect first-date look is always a great-fitting pair of jeans with an off-the-shoulder top and a pair of hoop earrings.” — Zoe Peretz
Jenny Bird
Slim Doune Hoops
$130
So pretty.
Silence + Noise
Grace Fitted One-Shoulder Top
$35
Exposed shoulders are underrated, IMO.
Madewell
Super Wide Leg Jeans
$118
For that perfect fit.
Pretty Top + Comfortable Pants + Everyday Jewelry
“When picking out a first-date outfit, I always focus on choosing a pretty top that flatters my collarbone and jewelry that fits my personal style. Since we’re typically sitting at a table or bar, that’s what they’ll be seeing the most, and I keep the rest simple.” — Kendall Becker
ROTATE
Metallic Crop Top
$98
I can confirm the fit of this top is so good.
Rag & Bone
Irina Ponte Wide Leg Pants
$225
Currently eyeing these.
Heaven Mayhem
Beanie Earrings
$115
So chic.
Long-Sleeve Midi Dress + Knee-High Boots
My co-worker Aniyah has impeccable style and shared that her date-night outfits consist of a sleek midi dress layered atop knee-high boots. It’s simple but sophisticated and now I want to try it out for my next date.
Freja New York
Mini Chrystie Oat
$268
Reformation
Jamen Knit Dress
$148
Little black dresses are always a great idea.
Schutz
Abbey Knee High Boot
$258
I’m in love.
Midi Dress + Sneakers
“I usually go for a midi dress with sneakers. Comfy, cool, and cute.” — Danielle Goldmark
GANNI
Bow-Embellished Pleated Organic Cotton-Poplin Mini Dress
$255
Simple and sweet.
Brandon Blackwood New York
Nia Bag
$575
Love at first sight.
Nike
Cortez Sneakers
$90
Comfort is key.
Silk Shirt + Cool Pants
“Silky button-down shirt with a cute lace bra peeking through with a pair of cool pants. A good pair of raw denim and low-heeled mules for something more casual, and then to dress it up a tad, I’ll go for flared pants that match the top for a monochrome moment.” — Vanessa Powell
Calvin Klein
Classic Button-Down Tunic Shirt
$89$36
Silk shirts are always a good idea.
Gap
High Rise Vegan Leather Cheeky Straight Pants
$35
A hint of trendiness is all you need sometimes.
Tony Bianco
Denver Mule
$160
