What Women Really Wear On Date Night

Date-night style is much more complex than pulling out your "freakum dress.” But, as usual, Beyoncé does have a point. Wearing an outfit that feels so foolproof, flattering, and you makes anyone exude confidence, especially on a certain Cupid-centric holiday. But, squeezing into a sexy dress is far from the only way to do it, and we've got 12 fashion insiders and style stars who can vouch for that. 

On any average day, the women ahead are wearing — and making — the designs that we’d often reach for come date night. And, as we found out, the styles they go to for their most intimate evenings don’t deviate much from what we see in public. Across the board, the models, muses, and fashion’s coolest business ladies could all agree that dating does not mean relying on a wardrobe of LBDs. And because they’ve all got strong sartorial POVs — and plenty of anecdotes when it comes to love — they bestowed their date-night pearls of wisdom on us. Read this before getting ready for tonight.  
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Photo:Matt Baron/BEImages.
Alexa Chung
TV personality, model, designer, and guest editor for Harper's Bazaar

What's your go-to date-night look?
"I went on a date last week…and I don't even remember what I wore. You know that moment you leave the house and you straighten your bed up? You know you’re open to being laid. So, I’m more interested in tidying the house and my hair."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"It’s all bullshit. You should just be whoever you are, and if they love you for that, then that’s great. I think it’s like false advertising if you’ve got on an outfit to catch a man. While it’s nice to walk into a room and have a man tell you you look beautiful tonight, it’s not necessarily what happens. I’ve been in a sweatshirt and underwear and they’ve been like, 'You look really pretty.' And, I’m like, ‘Really?’ So, who knows the inner workings of dudes' minds."
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Photo: Courtesy of Jenny Shimizu.
Jenny Shimizu
Booker at Elite NYC

Relationship Status:
"Married."

What's your go-to date-night outfit?
“Either leather jeans or a well-fitting denim ‘suit.’ And, for good measure, tube socks and a broken-in T-shirt. It makes me feel like Billy Jack or Mad Max and for me that is sexy times!”

If you’re being set up on a totally blind date, what would you wear?
"Same outfit as above. That outfit was like a good editor: It scared away the insecure and timid, and drew in the interesting and courageous.”

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
“Well, I do bust out a three-piece suit now more than ever because I want to complement my wife on certain occasions. She never asks me to dress up and she loves that ‘black tie’ to me means having a pair of clean jeans. I appreciate the juxtaposition in our very different styles."

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
“No. The best reaction would be a physical reaction. The most awkward, weirdest reaction was when they used the ‘I used to’ sentence. Example: ‘I used to have short hair/wear a leather jacket/walk with a slight limp,’ in order to point out what they saw in me was merely a reflection of themselves. That is a major red flag, people! A frenemy flag!”

What are your Valentine’s Day plans? And, what will you be wearing?
"Hopefully I will be watching my models walk the Alex Wang and/or Altuzarra shows! V-Day is a forced stressor and always falls in between NYFW (thankfully), so my better half and myself take a raincheck and celebrate in March. March is the new February.”
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Photographed by LaurenPerlstein.
Kitty Cash
DJ & fashion publicist

Relationship Status:
"Single."

What's your go-to date-night outfit?
"My go-to date-night outfit is a pair of high-waisted black denim, and either a sheer blouse or a cute cropped top with a pair of pumps or booties. High-waisted pants make me look long and accentuate the right assets. I don't want to feel uncomfortable or overdone. Not too much makeup, either — maybe some bronzer and a nice lip color, either nude or red. My must-have item is a signature scent from MiN NY." "

If you’re being set up on a totally blind date, what would you wear?
"I have never been on a blind date. I wouldn't stress out too much in this scenario. It is seriously a 50/50 chance you may or may not like your date. [Wear] flat shoes so you can run out of there if it goes bad."

Would you rather dress comfortably for a date or dress sexy? Are they one and the same?
"I think you can definitely dress sexy and comfortably. It's more in your overall personality and appeal. There are times when I feel very sexy in my sneakers and others when I feel sexy in my heels. It's about owning the look and having the attitude and confidence to go along with it. You might surprise yourself: Sometimes, I feel when I look uber-casual — meaning hoody, jeans, and sneakers — I get way more attention. It’s weird.”

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
"My date usually comments on my style, probably something like, ‘You have great hair/nails,’ or ‘I Iike your shoes.’ The weirdest comment has to be ‘Can I touch your hair?’ which is a big HELL NO."

What are your Valentine’s Day plans? And, what will you be wearing?
"I am not super big on Valentine's Day, but it is an excuse to get pampered. I am going to Aire Ancient Baths NY and having dinner prepared at home by a chef — the menu looks delish and has a Caribbean flair. I can't wait! I'm wearing a pair of G-Star high-waisted black jeans and an Alexander Wang cropped fuchsia leather vest, with black booties because I am not sure what trouble I will get into afterwards."
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Photographed by Martin Scott Powell.
Tziporah Salamon
Fashion consultant, teacher, actress, model

Relationship Status:
"Single."

What's your go-to date-night outfit?
"I have several. Any one of my many Chinese outfits — authentic 1920s Chinese pieces, pants, jacket, coat — heavily embroidered with peonies. I love the way they look, love the feel of the luscious silk against my body. I feel my best wearing them."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"My style does not change for my dates. I stay true to who I am. I dress for myself — always have, always will. I have a very strong sense of style, and any man who is not comfortable with that is not the man for me.”

If you’re being set up on a totally blind date, what would you wear?
"Any one of my favorite outfits, because it's what I feel best in and reflects who I am. A great Comme de Garçons jacket paired with a great pair of pants, or a great vintage dress with great shoes. Of course, I always wear a hat. The point is that I love all my clothes and hence have many options."

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
"Yes, people always comment on my style, usually with admiration. The flip side is that it can be intimidating to some — that's the price I pay."

What are your Valentine’s Day plans? And, what will you be wearing?
"Valentine's Day falls on Saturday this year and on the 10-year anniversary of my father's death. I will go to synagogue in the morning, dressed in my finery, in honor of the sabbath and in honor of my dear father. Later, when I go out to dinner with a friend, I'll probably have on something red, for Valentine's Day.”
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Photo: Courtesy of Rebecca Minkoff.
Rebecca Minkoff
Designer at Rebecca Minkoff

Relationship Status:
"Married."

What's your go-to date-night outfit?
"Tight jeans, great boots, and a leather jacket of some sort."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"I dress for me and if my husband likes it, that's a plus. "

Would you rather dress comfortably for a date or dress sexy? Are they one and the same?
"I think there is a way to do both. I am over suffering in pain for sexiness. If the heels hurt two steps in, they are coming off."

What’s the best piece of dating advice you’ve ever received? What’s the worst?
"Have fun and, as hard as it is, be yourself. That's the best way for someone to see you!"

What are your Valentine’s Day plans? And, what will you be wearing?
"Eating at Peter Lugers, drinking Champagne! Haven't planned my outfit yet, but since there are no kids with us, it's gonna be heels and a short dress for sure!"
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Photo: Courtesy of May Kwok.
May Kwok
DJ

Relationship Status:
"Single."

What's your go-to date-night outfit?
"I normally dress very casual: denim, T-shirt, sweater, and a nice purse and coat. I've always heard men like women who are more down to earth."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"I dress for myself, always! However, this doesn't apply when it comes to undergarments."

Would you rather dress comfortably for a date or dress sexy? Are they one and the same?
“Being comfortable IS sexy."

What’s the best piece of dating advice you’ve ever received? What’s the worst?
"Just be yourself and don't over-analyze every detail. The worst advice given to me was telling me to be patient with someone who was treating me badly."

What are your Valentine’s Day plans? And, what will you be wearing?
"I really try not to get too excited over V-Day plans, because something always comes together — be it with a special guy at the time or my good friends. I like the unexpected and, like most things, I plan the outfit right before it's time to go.”
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Photographed by Mark Iantosca.
Nicolette Mason
Blogger at NicoletteMason.com, contributing editor at Marie Claire, design strategist

Relationship Status:
"Engaged!"

What's your go-to date-night outfit?
"One of my favorite things to wear when we go out together is a leather skirt and a top that's just slightly sheer. My style tends to veer towards the more modest side, so it's always fun to spice things up with a little hint of skin showing."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"Honestly, it doesn't. I'm proud to say I absolutely dress for myself. I've had exes try to influence my style or dictate how I should dress and I absolutely resented them for it. (And obviously our relationships didn't work out!) Personal style and fashion is a huge part of my identity, so anyone who expects me to dress for them and not for me is going to have to kick the curb! My partner really encourages me to dress however I want, and I love that about her. She hates on some of my quirkier sunglasses, though!"

What’s the best piece of dating advice you’ve ever received? What’s the worst?
"Best advice: Don't take anyone's bullshit. Worst: A friend once encouraged me to stay in a really crappy relationship even though I didn't feel things were right. I'm glad I didn't listen!"

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
"I once wore a pair of glittery cat-eye sunglasses (the Miu Miu Noir frames — they're amayzing), and my date said they were too distracting. I mean, whatever. It's called fashion — look it up!"

What are your Valentine’s Day plans? And, what will you be wearing?
"My fiancée, Ali, is surprising me with plans the night before, since Valentine's Day is in the middle of fashion week! I have no idea what we're doing and I'm slightly nervous about it. I'm definitely the planner in our relationship!"
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Photo: Courtesy of Cleo Davis-Urman.
Cleo Davis-Urman
Cofounder and director of creative relations at Tinker Tailor

Relationship Status:
"That's an interesting question."

What's your go-to date-night outfit?
"I’m never a monogamist when it comes to clothes, but recently I have fallen in love with the perfect, army-green, tailored blazer that was given to me by a dear friend. Not only does it fit like a glove, but because it once belonged to someone special I feel great every time I wear it. Paired with my favorite denim and my lucky Kazuko crystal necklace, I am ready for whatever the evening brings."

If you’re being set up on a totally blind date, what would you wear?
"When I was set up on my first blind date I asked my friend and mentor Brad Goreski for some style advice. His reply: Wear Jason Wu! The designer's feminine yet subtly sexy aesthetic is perfect for falling in love."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"My approach to style doesn't change. I dress to express myself, and my romantic, personal, and professional lives intersect — dating is just an extension of everything else."

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
"A truly great look is a subtle success that needs no comment!"

What are your Valentine’s Day plans? And, what will you be wearing?
"This year, it falls on the busiest day of New York Fashion Week, which means runways, runways, and more runways. I won't be celebrating in any real way, but will acknowledge the occasion by wearing my hot-pink glitter Rodarte coat."
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Photo: Courtesy of Kaelen.
Kaelen Haworth
Designer at Kaelen

Relationship Status:
"Married."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"My approach doesn't really change much. I think my husband has accepted that I'm going to do me in terms of wardrobe. I'm dressing for myself, but of course you want your man to think you look good, too. He's pretty progressive, though, so he's usually on board with my sartorial decisions."

Would you rather dress comfortably for a date or dress sexy? Are they one and the same?
“I think they are absolutely one and the same. You cannot feel sexy if you are uncomfortable. Sexy is a state of mind, and I wholeheartedly believe that.”

What’s the best piece of dating advice you’ve ever received? What’s the worst?
"The best advice is the most obvious: Don't be a version of yourself that you can't sustain. Be true to yourself and be honest. The worst advice is probably something along the lines of 'order a salad when you really want steak.'"

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
"He usually just tells me I look nice as opposed to commenting directly on something I'm wearing. Unless it's a really special piece. That's always the best reaction. The worst reaction would be just the question ‘What is that? Are you wearing that for real?’ in response to a sweater onesie that I did, in fact, wear."

What are your Valentine’s Day plans? And, what will you be wearing?
"I don't know; hopefully my husband made some. Unfortunately, since Valentine's day falls during Fashion Week, it's usually not top of mind. That sounds bad, but he understands. I think.”
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Photo: Courtesy of Jessica Hendricks.
Jessica Hendricks
Founder of The Brave Collection

Relationship Status:
"Engaged."

What's your go-to date-night outfit?
"When we go out during the week in Brooklyn, I wear skinnies with a low-cut jersey tank — my Alexander Wang tank is my absolute favorite. I feel effortless, sexy, and comfortable in it. When we go out on the weekends, I like to play dress-up with layers of lipstick and an aggressive arm party."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"Me! Maybe I’ll unbutton a button or two, and I lather up in my Bvlgari Au Tea Vert lotion, which makes me feel like a fancy woman of the world."

Would you rather dress comfortably for a date or dress sexy? Are they one and the same?
"I think clothes should be an extension of all of your fabulousness inside, not constricting or binding. I’m definitely better off in something comfortable where I feel like me — I think comfortable is sexy.”

What’s the best piece of dating advice you’ve ever received? What’s the worst?
“The best was that you should marry someone who you would go into business with — meaning that the relationship must possess trust, mutual respect, and common values, not just a sparkly emotional or sexual connection. The worst advice was to stay in a relationship where the physical connection wasn’t quite there — I learned that boring leads to boring.”

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
"I bought these black leather converse sneakers and I couldn’t tell whether or not to keep them so I asked my fiancé, and he told me I looked like ‘a model off duty.’ Obviously I kept them after that. Now, we call them my Kendall Jenners. The weirdest was when I was dating this guy in college when I used to dress in tight leopard leggings and massive '80s sweaters with fire red lipstick, and he told me I looked like a 90-year-old woman.”

What are your Valentine’s Day plans? And, what will you be wearing?
"We are headed to Vinegar Hill House — that magical little escape! I’m going to wear these gorgeous opalescent Melissa Joy Manning earrings my fiancé got me for the holidays, and a matching two-piece crop top situation from Reformation that I die for.”
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Photo: Courtesy of Sydney Reising.
Sydney Reising
CEO/founder of Sydney Reising Creative

Relationship Status:
"Single."

What's your go-to date-night outfit?
"Jeans and an oxford. Nothing beats a crisp, white oxford. That's my definition of classic, simple, sexy."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"I dress for me. I'm pretty standard in my clothing choices — I know what I like and stay with it."

What’s the best piece of dating advice you’ve ever received? What’s the worst?
"Best: Be yourself. Worst: Join Tinder."

Does your date normally comment on your style? What’s the best reaction you’ve heard? What’s the weirdest?
"Not really. Once someone said I looked expensive..."

What are your Valentine’s Day plans? And, what will you be wearing?
"Fifty shades, obviously — and I'll be wearing kinky lingerie under my jeans, trust me. "
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Photo: Courtesy of Raquel Allegra.
Raquel Allegra
Designer at Raquel Allegra

Relationship Status:
"Engaged for 6 1/2 years."

How does your approach to style change, if at all, when it comes to your romantic life? Are you dressing for your partner or for yourself?
"Lucky for me, my man loves me without makeup, and in sweats! I always dress for myself first, but there's no denying the importance of 'dress to impress.’ When I REALLY want to get my man excited I'll wear tight vintage Levi's and a loose button-up blouse — no bra and half-unbuttoned — drives him wild.”

Would you rather dress comfortably for a date or dress sexy? Are they one and the same?
“In my book, comfortable and sexy are one and the same. My favorite sexy look usually includes a blazer, a pair of cozy track pants, and some high, but not TOO high, heels.”

What’s the best piece of dating advice you’ve ever received?
"If you don't belong…don't be long!"

What are your Valentine’s Day plans? And, what will you be wearing?
"Sofa city, baby! Take out and a movie: No clothes necessary!"
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