11 First-Date Outfits My Single Friends and I All Swear By

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(Image credit: @anna__laplaca)

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 T-shirt or dressy 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

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(Image credit: @amaka.hamelijnck)

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.

Flirty Top + Leather Pants + Platform Boots

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(Image credit: @emmarosegreis)

"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

Statement Top + Flattering Jeans + Heels

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(Image credit: @_sierramayhew)

"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

All-Black Staples

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(Image credit: @just_a_taste_of_fashion)

"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

Oversize Shirt + Tights + Knee-High Boots + Blazer

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(Image credit: @kellychristinereed)

"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:

Leather Jacket + Fitted Top + Print Pants

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(Image credit: @anna__laplaca)

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.

Jeans + Off-the-Shoulder Top

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(Image credit: @luciacuesta_)

"My perfect first-date look is always a great-fitting pair of jeans with an off-the-shoulder top." — Zoe Peretz

Pretty Top + Comfortable Pants + Everyday Jewelry

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(Image credit: @kendall_becker)

"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

Long-Sleeve Midi Dress + Knee-High Boots

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(Image credit: @ali_tate_cutler)

My co-worker Aniyah has impeccable style and shared that her date outfit consists 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.

Midi Dress + Sneakers

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(Image credit: @champagnemani)

"I usually go for a midi dress with sneakers. Comfy, cool, and cute." — Danielle Goldmark

Silk Shirt + Cool Pants

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(Image credit: @aninebing)

"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

This story was originally published at an earlier date and has since been updated.

Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.