What I Wore When I Fell In Love

A little black dress vs. big gray sweatpants — does it make a difference what you're wearing when you meet the love of your life?

Costume designer Edith Head is famous for suggesting, “You can have anything you want in life if you dress for it.” But does that apply to everything? Even true love?

I feel my best when my skin is gleaming, outfit is runway-ready and my hair is tousled to the sky,” said fashion and beauty influencer David Ruff, who was wearing ratty workout gear when he ran into his ultimate crush, Shawn Mendes. “But your look, like life and love, won’t always be perfect,” Ruff said.

Indeed, there’s something liberating about attracting your heart’s desire when you’re feeling less than fresh. But the question remains: Are you more likely to fall in love when dressed to the nines or when you’re barefaced, wearing athleisure? Below, fashion influencers known for their killer sense of style reveal what they were wearing when they found love.

Carina Chaz, founder and CEO of DedCool

“I met the love of my life when I had sworn off dating. On a nondate in the park, microdosing mushrooms, I’d dressed for comfort: an oversized Aerosmith vintage T-shirt, a pair of mid-rise, faded red, ankle-cropped Mother jeans and platform Dr. Martens boots. I’ve been on a vintage kick to live more sustainably and in sync with clean beauty practices. I feel most confident by being good to myself and the environment.”

Dr. Martens boots made their way into two love stories on the list.
Christian Vierig via Getty Images
Dr. Martens boots made their way into two love stories on the list.

Sibyl Buck, musician, model and yogi

“I was wearing a red tank top with thin blue ringers around the armholes, a low-cut undershirt and my favorite bell-bottom Lees from the ’70s. My skin was awful! When I stopped modeling, it went crazy and looked like a heat rash all over my face and neck. I was deeply humbled. I was fronting my band that night, and I used swagger and the heavy music to make my angry-looking skin part of my frontwoman look. And that’s the night I met my beloved.”

“It was Valentine’s Day and we were going to dinner with a group of people at a restaurant in Hollywood. I was cute casual, nothing too fancy. Makeup was minimal to none. I had on cream highlighter and that’s it. I felt great in my skin. Being natural is when I feel most confident. It’s when I start layering on the makeup (Does my lipstick look all right? Is it smudged?) or when I do my hair (Are my curls flat? Did my blowout get frizzy?) that I start feeling less confident. The less effort I put into my look and the more effort I put into overall health and happiness, the better I feel and look.”

Susan Korn, founder and designer of Susan Alexandra

“I had just come from a dinner with some girlfriends, so the mood of my look was decidedly femme and soft, not sexy and adventurous. I’m always 70% uncomfortable in my skin and that’s just me. But this was summer and I was tan and my hair was long. I feel most divine in a summer dress. It’s as good as I get. This one was sheer, black and vintage with an uneven fluttering hem. It had a mix of pink polka dots, pink roses and trails of sparkly thread throughout. Dresses are God’s gift to romance, and even with the little heel I was wearing, I felt tall and cool, cinematic and, dare I say, charming!”

Jiashan Liu, designer

“I was working for New York Fashion Week. He was modeling in shows. We met when he faked running into me, then asked to take a picture. I was wearing a black tube top with thin spaghetti straps, black flowy pants, an oversized white shirt which I stole from my dad and platform Dr. Martens. I did my everyday signature winged eyeliner, paired with a little highlight on cheeks and nose, and gloss from YSL to finish. I used Dior’s Sauvage, which reminds me of a mysterious forest. The overall look was sexy without trying too hard. I like to show off my figure but love the empowered feeling that comes from oversized clothes.”

Sometimes, a vintage Aerosmith T-shirt can be just as romantic as a little black dress.
Marc Broussely via Getty Images
Sometimes, a vintage Aerosmith T-shirt can be just as romantic as a little black dress.

Lindsay Jones, creative director, designer and advocate

“I was looking through vintage books in Paris. At the time, I was into wearing silk robes and silk pants with Gucci slippers and socks. Think a power femme version of Hugh Hefner. I used to be a dirty punk rock gangster and still am, so it’s fun to clean up and hold presence in a room. Clean, exfoliated skin is the look, with Nars matte lipstick and blush in Orgasm, plus Milk cosmetics’ Kush Mascara, which gives major BDE. I have a Sephora addiction. These are my go-tos when it comes to casual seduction.″

Samantha Conn, founder and creative director of Luna Skye

“I host dinner parties every month at my house. Musicians of all kinds gather for food and drinks. One of my oldest, greatest friends brought this guy along. It was a really casual environment with no pressure or expectations. I remember I was wearing Le Labo Santal. I’m always wearing Le Labo Santal, which has embedded itself in my clothing and skin so even when I haven’t applied it, it lingers. I was dripping in jewelry. This is when I feel the most beautiful and confident — minimal, but put together.”

Madison Williams, TV producer, host, fashion blogger

“The night I fell madly in love with my now-fiancé, we had just moved to Los Angeles and he threw me a masquerade party. I wore a little black dress. It was a tight, short-sleeved, one-shoulder number and I wore a pair of pewter-colored Juicy Couture pumps. I opted for a mask that was structured and dramatic, with one side silver and the other black. I wore it more as a headband to show off smoky eye makeup. To top it all off, a spritz of Britney Spears’ Fantasy perfume. I remember feeling SO confident that night about myself, my outfit, my relationship with Sonny and my future.”

MacKenzie Crawford, shop owner, Babes on Legs

“On this particular first date, I remember planning my outfit as if to warn him, ‘This is what it will be like with me.’ Business on top, party on the bottom! I wanted to be taken seriously as a responsible, mature adult, so I opted for a sheer black turtleneck paired with a black leather bomber jacket with brown mink-lined collar and cuffs, which gets the most compliments from strangers when I’m out. I went for Pucci pants with a mint green and gray swirl print with little triangles all over them. I paired those with cow print boots. I always wear something I’m really comfortable in so that I have one less thing to feel anxious about when meeting someone for the first time.”

Matthew Milèo, owner/creator of Milèo New York

“At the research lab at school, I froze in my tracks for what seemed like an eternity when I saw the new grad student. My first thought was, ‘What the hell am I wearing right now?’ The outfit was a flannel hoodie with baggy AF corduroys, neither of which showed my body. Within 10 minutes, my newfound crush says he’s not into baggy clothes. In that moment, the need to undergo metamorphosis could not have been greater. I spent hours trying on clothes that were fitted. I tailored some. Looking back, I was probably concealing myself because I didn’t want to be noticed in a sexual way yet. But he shook me to my core and I let go of the baggy body armor.”

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