What Do You Wear on First Dates?

Recently I was noodling around on Instagram when a question by stylist Amanda Murray caught my eye: “What do you wear on a first date?”

My last first date was six years ago at an Italian restaurant with a funny guy who had hot hand tattoos and dimples. My outfit of choice? A chiffon swing dress and too-high heels that made me hobble. Looking back on that outfit makes me giggle. Instead of leaning into my personal style — say, platform sneakers and maxi dresses — I was more concerned about achieving an old-school “first date look,” alluring and polished.

Since then, so much has changed. New couples quarantined together during a pandemic. Women are opening up more and more about what they want in bed. People are wearing fanny packs — voluntarily! So, are daters still trying to look like shiny 2.0 versions of themselves? Are magical dating dresses still a thing?

Curious, I asked three single women about the dating looks that never fail them…

Ethaney Lee, 34, Berkeley, CA
A little black dress

“I recently went on a first date after getting out of a five-and-a-half-year relationship with my ex-fiancé and I had no idea what to wear. Younger me would have worn something that made me feel sexy albeit uncomfortable. But older me wants to feel sexy and comfy. With the help of my best friend, I chose a low-back black dress and my signature shoe Onitsuka Tiger sneakers. I paired it with minimal makeup and felt effortless and chic. It was how I like to dress in everyday life, date or no date, which made it easier to be myself when I am struggling to remember how to date in the first place!”

Victoria Lacon, 27, Dallas
Jeans and a nice top

“I wear a signature outfit on all my first dates: an emerald green long-sleeved top, straight-leg jeans and Superga sneakers. I prefer jeans for first dates because I like to feel covered and not worry about a skirt riding up. I wear it on repeat because it’s so hard to find an outfit that you look and feel good in, plus the people you meet don’t know you’ve worn it on the three other dates before them!”

Jordan Sondler, 33, Brooklyn
Matching sets

“I’ve been dating for six years, and over time I’ve learned to lean into clothes that make my body feel comfortable and unconstricted. I like pairing a fun matching set with a denim jacket. Sets feel like something you’d lounge in at home, and you can always use statement pieces like a beaded bag or bold hoops to elevate a casual outfit. Whenever I deviate from these pieces and wear an outfit that’s tight or has multiple layers, I find myself worrying about whether I’ll get all sweaty and flustered by the end of the date.”

Now it’s your turn: what do you wear on first dates? Please fill us in…

P.S. A first date conundrum and first date rituals.