From Overalls to Slips: 7 Women on What They Wear to Feel Sexy

There is a moment in Mad Men (yes, I’m years behind) wherein Roger instructs Joan to “wear something sexy.” Putting aside (for now) the fact that Roger is a misogynist asshole, his request made me think: What is “something sexy”?

The word “sexy” is so subjective that it’s almost polarizing. What I picture in my head when I hear it (the car washing scene in Cool Hand Luke, Gilda’s hair flip, Rihanna, generally) is worlds away from how I picture myself within its context. My antiquated associations with the word are not at all reflective of the complex thoughts I maintain about everything it can mean. And despite the fact that I know how to dress when I’m asked to look professional, or casual, or fancy, with sexy? I’m not so sure.

Rather than contemplate this complicated directive all on my own, I asked a few women whose style I admire to interpret the word themselves. While each of their outfits were totally different, the one thing everyone seems to agree on is that “sexy” is more a state of mind than anything else.

Crystal Anderson

Crystal is Operations Manager and event producer at Man Repeller.

Why this outfit?

I bought this dress this summer and I literally have never felt sexier in my entire life than when I wear it. Reformation has a way of cutting its garments to hang on a woman’s body like they were made specifically for her. It shows just the right amount of cleavage and accentuates my collar bones. I’m an equal opportunity dresser and don’t like to wait for an “occasion” to wear something. I don’t think of myself as typically sexy, so I’d wear this dress to work, on a date, brunch — wherever.

What is your personal definition of sexy and how has that definition evolved over time?

I saw a shitty ad on the train the other day that said,“Finally, Sexy AND Comfortable,” and I thought, What a load of bullshit. These things have never been mutually exclusive for me. My definition of sexy is the way my body feels. I feel sexy when my girlfriend looks at me from across a crowded room. Sexy is me naked after a hot shower, slathered in goat’s milk Shea Butter. Sexy is sweat on the back of my neck after sex. Sexy isn’t always a clothing option, it’s a way of life.

I think people used to think of sexy as a negative thing. As if being sexy meant you couldn’t be smart and beautiful and commanding. You were just the sum of your parts; a siren to be ogled. These days, women are reclaiming the complexities and intersections of the word. It means so many things and is a badge of honor and I say to all you sexy women out there: I’m proud of you! Keep doing the damned thang!

The sexiest song of all time is:

Hands down, “Darling Nikki” by Prince.

Anum Bashir

Anum is the Founder of Desert Mannequin, MR contributor, a podcast host, and co-creative director of NDUO.

Why this outfit?

The “sexy” genre is something I feel I know nothing about and this was a total mental freeze (sartorially speaking), so I thought I’d outsource the styling — my husband actually styled me from the ankles up. I only had a say when it came to the shoes. It was interesting because by the time he was done, I actually did feel sexy, and loved the look. It was cute… we bonded! He made me feel good about myself.

I find black to be a color of confidence, and looking/feeling confident to me is what comes across as sexy. The blazer’s sleeves add so much drama; the tights show off the shape of my legs without actually showing them off. The purpose of this outfit was to also come across as relaxed and not too stylized. I’m a relatively modest dresser so we were trying to achieve sexy through modesty. I think we did quite well. The red lip and pearl earrings added an air of sophistication to the whole look.

I think the last time I truly aimed to look “sexy” was in college. (Think: a tube top dress at a house party.) Ever since I got married my style has evolved so much, but I’ve never felt more like myself than right now.

What is your personal definition of sexy and how has that definition evolved over time?

Confidence, boldness, taking ownership of what you choose to cloak your body with. A smile, and good eye contact. It hasn’t changed. I just express it differently.

The sexiest song of all time is:

Oh man, there are quite a few, but “Wicked Game” by Chris Isaak is a good one. “Pour Some Sugar on Me” by Def Leppard. “Gett Off” by Prince. Lots of stuff by Beyoncé!

Claire Beermann

Claire is an editor and writer at ZEITmagazin and the founder of C’est Clairette.

Why this outfit?

The outfit makes me feel sexy because it makes me pleasantly aware of, yet not self-conscious about, my body: The blazer accentuates my waist, the trousers are fitted on the hips and butt, the high heels make my legs appear longer and lend my posture an S-shape. It may sound funny, but this outfit actually reminds me that I have a body while not exposing too much of it, and that I find sexy. My idea of a sexy outfit makes me feel like my body is right here with me, ready to do anything.

I’ve come to realize that I actually don’t dress for occasions anymore — I just follow my gut. One day I’ll wear something really boring to a party, and then the next morning I’ll wake up and feel like going to work in a funky cocktail dress. I could actually totally see myself wearing this outfit to the office because it’s a place where I want to feel confident and powerful, and that’s what this outfit does for me.

What is your personal definition of sexy and how has that definition evolved over time?

“Sexy” for me is much more about feeling than of looking a certain way. My calculation is that if I feel sexy, I will also look sexy – whereas dressing “traditionally” sexy doesn’t always lead to feeling sexy. I personally don’t feel sexy in a miniskirt (it makes me worry about my legs the whole time), whereas a really good song I’m dancing to in my bedroom while dressed in sweatpants can make me feel very sexy. An outfit that makes me feel sexy is one that doesn’t force me to tuck in my stomach or walk in a certain way but one that lends me confidence and grace. I really think confidence is the key to sexiness.

I think I’ve always thought that way. Unlike my mom, who once famously dressed as a dominatrix to go to a costume party with her shy boyfriend of two weeks (my dad!), “sexy” for me never meant “meet me in the bedroom.” I’m not judging anyone who thinks that way and I admire my mom for her bravery! I just know myself: I probably wouldn’t stop giggling if I “surprised” my boyfriend with sexy lingerie. Or maybe I’m immature.

The sexiest song of all time is:

“Vogue” by Madonna. Makes me feel like I own the town.

Jac Cameron

Jac is the co-founder and Creative Director of AYR.

AYR high rise skinny jeans, thrifted black turtleneck -- similar here and leather jacket -- similar here, Soludos heelsAYR high rise skinny jeans, thrifted black turtleneck -- similar here and leather jacket -- similar here, Soludos heels

Why this outfit?

Jeans always make me feel sexy, especially a high-rise skinny with a heel. A jean that truly fits perfectly. Something that hugs and holds and makes me carry myself more confidently is my “go-to” when I’m trying to feel sexy. I love the way these heels frame my foot and ankle in such a flattering way. I always tend to feel sexy in a jacket, especially this little vintage leather one. Something about the fit — the slim sleeve and the leather — makes me feel powerful and confident.

What is your definition of sexy and how has that evolved over time?

Feeling good in my body and my clothes stems from a place of confidence. I dress to feel sexy and confident for myself first, to feel in touch with my body and, in turn, great in my clothes.

When I was younger, I felt that “sexy” was a way of dressing to attract attention. That changed as my opinion of design evolved. What is prescribed as a “sexy” garment traditionally did not fit with my personal opinion. Growing out of those prescribed ideas in my mid-twenties opened up my view on what it means to feel confident and dress truly for myself.

The sexiest song of all time is:

“Nightclubbing” by Iggy Pop (obviously).

Jennifer Buckingham

Jennifer is a fashion and lifestyle blogger.

Why this outfit?

I am obsessed with this dress — emerald velvet, deep V-Neck, and kimono sleeves. It makes me feel sexy because of the cut and the way it flatters my curves. It has the dramatic flair I always like to include in my sexier outfits. I love any excuse to dress up, and I usually express my sexier side via evening-wear. I always love to go that extra step, whether it’s for date night, an event, or out with my ladies for drinks.

What is your personal definition of sexy and how has that definition evolved over time?

My personal definition of sexy is finding ways to own and empower myself in my sensuality and sexuality as woman on my own terms. I find that feeling sexy is a lot about a mentality and can be expressed through a bunch of different fashion choices, and most importantly in just being authentically yourself.

When I was younger I definitely wanted validation that I was sexy from the opposite sex. What I’ve now learned is that it is about validating myself and feeling it, whether I am walking into a room dressed in my best or just out of the shower singing/dancing in front of a mirror. I’ve learned to appreciate the different sides of sexy in myself.

The sexiest song of all time is:

“Black Dog” by Led Zeppelin.

Juliana Salazar

Juliana is a freelance stylist, brand strategist and contributing writer for Man Repeller.

Why this outfit?

I would have never deemed this a “sexy” outfit per se, but I recently wore it out one night and felt really great in it — comfortable, confident, cool, all the things. I also have never been approached more by guys at a bar, so there’s that.

I am honestly never inspired to put together a traditionally “sexy” look. The last time I can remember doing so was for a boyfriend years ago and I classified it as a gift.

What is your personal definition of sexy and how has that definition evolved over time?

To me, sexiness has nothing to do with superficial or physical seduction and everything to do with your attitude and how you carry yourself. If you feel good within your own body, that radiates stronger than anything else. I find that the most attractive people are so comfortable in their own skin that that’s what is intriguing about them — they have a way about them that makes you want to know more.

I’m not sure when [sexiness] began equating to skin-tight dresses and cleavage (if not a straight-up lack of clothing), but I’m going to assume that just comes from a long history of women’s bodies being viewed as prizes. I think people like Phoebe Philo, a woman designing with the modern woman in mind, and Leandra (!) really helped to push the notion that we can wear things for ourselves rather than our audience.

The sexiest song of all time is:

Hmmm, this is tough. Probably some Jeremih song, or Beyoncé.

Nina Wheeler (me)

I’m a freelance writer and the Brand Director at AYR.

Why this outfit?

For me, the sexiest thing is a combination of slouchy and seductive; like a voluminous but slightly sheer dress, or overalls over lingerie. I think my sexy aesthetic has an element of appearing unintentional — even though that’s not always the case.

I think it basically boils down to when I want to be noticed, which is far more about a mood I’m in than a specific occasion. If I’m feeling myself, drinking wine and listening to music while getting dressed, often that’s when I’ll decide to bust out the sex appeal and it doesn’t really matter where I’m going or who is going to be there. I should mention that when I was single, I’d definitely dress in my version of sexy when I knew I’d be seeing someone I liked, but only if it was a group situation — I’m either never brave enough or never inspired to put on a sexy outfit for a one-on-one meeting.

What is your personal definition of sexy and how has that definition evolved over time?

A lot of it is about the dichotomy between being comfortable with yourself and being willing to leave your comfort zone. Confidence is appealing, but I think what brings confidence into the realm of sexy is an attitude of openness and an interest in other people. If someone looks me in the eye during a conversation, nails the flirty banter, makes me feel heard…they could be wearing a burlap sack and I’d still find them sexy.

When I was younger, I thought there was a formula to being sexy: Straighten your hair, wear skinny jeans and a loose, low-cut top, etc. I also thought there was a way to act sexy, which I have since determined there isn’t. If you can be yourself, if you can take ownership of your look, your body, the energy you’re putting into the world…that’s as sexy as it gets. I’ve also slowly gotten/am getting over the need for validation — if I think it’s sexy, then it is. It doesn’t matter if anyone notices or agrees with me.

The sexiest song of all time is:

“Is This Love” by Bob Marley.

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