What I Wore On the First Date with My Guy: Who What Wear Edition

First date stories are always a crowd-pleaser, and here at the Who What Wear HQ, what we really want to know (unsurprisingly) is: What you were wearing? So we asked our staffers to dish on all the outfit details from their first dates with Mr. Right. Scroll through to read about the flared jeans, high-top sneakers and silky button-downs that helped win their guys’ hearts.  

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Who What Wear

“I kept it really simple with skinny jeans, a black top, a black leather bomber jacket, and ankle boots. It was January in New York City, so I was probably freezing in that outfit. There was also a grey leather handbag, which became a first-date casualty when a drink was spilled on it at some point. It's been six years since that date, so I guess there's something to be said for simplicity!” – Allyson

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Who What Wear

“The first night that I hung out with my husband—eight years ago now—I wore my favorite well-loved 1921 Denim flare jeans covered in hand-sewn patches (and he was wearing his favorite hand-sewn patch jeans—a major talking point), a pink Patagonia Live Simply T-shirt, a vintage scarf in my hair (because I had been surfing all day and didn't want to brush it), and my trusty old Birkenstocks (way before their fashion resurgence—always a trendsetter, clearly). And I still have this entire outfit because I am incredibly sentimental.” – Jenna

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Who What Wear

"I wore nude Repetto ballet flats, waxed black J Brand jeans, a halter from Reformation, and a vintage jean jacket. While I sometimes sub the jacket for a fun blazer, I am without fail, a flats on the first date kind of gal." – Julia

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Who What Wear

“On my first date with my boyfriend seven years ago, I wore a T-Bags cotton dress. I remember it had a deep-V and featured a colorful print. I paired it with my trusty Frye ankle boots for a look that was approachable and feminine. I would never wear an outfit like that now, but back then, it certainly did the trick!” – Kat

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Who What Wear

"I wore my all-time favorite, go-to Mackage leather jacket with a basic white tee, dark wash skinny jeans, and high-top white Converse. Since day one, we've been keeping it casual. That is, until he popped the question six years later." – Raleigh

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Who What Wear

“I wore white J.Crew shorts and a blue-and-white striped cardigan from the now defunct Rugby Ralph Lauren line. It was a baseball game, but instead of sneakers I wore gold Jack Rogers Navajo sandals. I guess it worked cause we're getting hitched!” – Liz

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Who What Wear

"Our first date was a blind date, so I wanted to keep things simple yet polished. I went with an ochre just-above-the-knee structured skirt from Prada, with a white loose-fitting shirt that I tucked in. I knew he'd be 6'4” compared to my 5'5” so I wore heels!" – Megan

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Who What Wear

“On my first date with my now ex-boyfriend, I wore an off-the-shoulder black top, white shorts, and nude wedges. I remember it perfectly—it was 2008, in the middle of the summer in Kansas, and I had sunbathed all day so I was super excited to show off my bronzed legs.” – Michelle

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Who What Wear

“It was August in NYC. My outfit: a sheer, printed tank top from Anthropologie, which I tucked into a black pencil skirt and wore with my brand new Vera Wang wedge—they were bright patent pink, I loved them so much. I carried my Furla tote in python-embossed gray leather. I distinctly remember my feet hurting. We're still together two years later, which just proves a good outfit can take you a long way." – Meghan

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Who What Wear

"I wore a silky, oversized Equipment button-down shirt, slim jeans, and my favorite pair of mules. It felt like a good balance of casual and sexy!" – Riley

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Who What Wear

"My first date with my guy (who now happens to now be my husband) took place 13 years ago. Today, my outfit would be considered horrendous, but at the time it felt quite relevant. We went to the beach, walked the sand dunes, and watched the sunset, so I went the casual route: I wore low-rise Abercrombie & Fitch flared jeans, a thin white studded belt from Hot Topic (yikes), sandals, a shelf tank (with a hint of midriff, of course—it was 2001!), and a knit cardigan from Nordstrom's Brass Plum section that swept past my knees and tied at the waist. In retrospect, I'm pretty sure this Britney-Spears-circa-Crossroads-inspired ensemble was perfect for the occasion...and it clearly won his heart!" – Alex

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Who What Wear

"Our first date was planned for a Sunday brunch. I was running late of course, so I threw back on the neon hot pink sheath dress from my girls' night out the night before, along with a pair of black leather studded sneakers (to keep it causal, right?!). Wasn't my finest fashion moment, but luckily he was really into my juxtaposed style that day, and he still talks about how badly I stood out in that ‘50s style diner." – Shanelle

What did you wear on your last first date? Tell us in the comments!