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As a general rule, if I’m meeting someone for the first time, I wear clothes that make me feel very much like myself — a security blanket outfit, if you will. That one striped sweater I’ve replaced three times, the flannel shirt I’ve had since college, those flowy, high-waisted pants I always get compliments on.
But there are occasions where my ratty flannel just doesn’t work, and if someone I actually like is taking me out somewhere a little fancy, I want to make sure I look good. As I’ve eased myself back into the dating game, one thing more than any other has become abundantly clear: My date night wardrobe is not on point. Whoops.
So rather than blowing money trying to re-stock my options, I figure I’ll crowdsource a little advice: What are other people wearing out on dates?
Here, Racked editors and some readers share their best tips for what to wear on the first date and beyond. Want to share your own go-to? Tell us about it in the comments.
What should you wear on a date? NOTHING! Hahahaha! Just kidding, you should wear a dark floral dress (I love to look like my Bubbe's wallpaper) along with opaque black sweater tights and your favorite jacket if it is cold. The dress should be short but not too short, tight but not too tight, and relatively easy to remove should the date go extremely well or so terribly that all you want to do when you get home is rip it off and take a long, long shower. (Another piece of advice: Sitting down in the shower can eliminate most if not all bad date-related ennui.) This is the sort of dress that magazines describe as "flirty," which is annoying, but also accurate. —Alanna Okun, senior editor
On a date, I like to be me. I never dumb down my style, but just keep it a little simpler. A little less makeup, a little less jewelry, but always hoop earrings and black jeans or a black skirt, and always cute shoes — usually boots of some kind. —Emily, Boston
My go-to first date outfit is skinny jeans, high heels, and a T-shirt — preferably a soft, slouchy, vintage T-shirt. From there, it depends on the weather: a leather jacket in the spring, an oversized men's sweater under a coat in the fall. It's both the outfit I feel most comfortable in and one that I think works for just about anywhere in NYC. —Britt Aboutaleb, editor-in-chief
I'm going to out myself as someone who goes on a lot of first dates, so I'm kind of an expert here. I usually start with a base of jeans and prefer a leather jacket and some sort of comfortable-enough heel (ankle boot, suede slide). What I layer on top of that is usually dependent on the guy, the place we're meeting, and of course the weather.
I've been going for cozy, form-fitting sweaters with a little bit of sparkle in the form of jewelry (a conversation starter if done right) in these colder months, but when we had a warm spell a few weeks back, I picked a fun floor-sweeping tie-dye dress with really high slits — still with jeans on. Bottom line? Have fun, be comfortable, and above all, feel like yourself. —Laura Gurfein, deputy managing editor
I would wear the one T-shirt that was low and sexy without looking like I was going for low and sexy, with skinny jeans and Chucks. —Amber, Brooklyn
My rule of thumb for first date outfits has always been to wear what you feel most comfortable in, which is why on my first date with my now-boyfriend I wore a pair of black high-waisted jeans and a black turtleneck. When I showed up to the bar, he was essentially wearing the same exact thing. It was a hilarious icebreaker then, but a pretty standard occurrence now a year later. —Tanisha Pina, associate market editor
Let's see, for a casual, non-food-centered date: leotard and tomboyish jeans. For a fancier and food-ier date: a slip dress, or a sheer or lace dress with a slip underneath, or jeans with a silky button-down. I like it when at least one piece makes me feel like I'm lounging in my PJs and/or underwear. Plus, a slip dress is cute while allowing for max pasta intake. Red nails, little rings, minimal makeup — never lipstick. —Nicole, New York
If it's a dinner date, my go-to outfit is always brown loafers and a brown belt (black is too formal), dark blue trouser pants (brown and blue always looks good), and then any formal, button-down, long-sleeved (major key, so sleeves can be rolled up nonchalantly) shirt in colors like burgundy or white, tucked in. The only thing to be careful of is making sure the shirt isn't too office-y, which is why I stay away from light blue. If it's a super formal spot, I’ll top it up with a jacket. —Fahad, Karachi, PK
I usually wear some formula of high-waisted jeans and either a loose sweater or button-down worn slightly open. The jeans are kind of the non-negotiable, because they’re what I’m the most comfortable in, and I want to be casual. I feel a little too done-up in dresses or skirts on first or second dates. Plus, every restaurant that I'd end up in in New York has a lax dress code anyway.
My main thing is I want to be comfortable and I don't want to be tugging at my clothes — if we're going out to dinner, I'm not wearing a tight dress because I want to eat! And I don’t want to be thinking about where that dinner is sitting on my body. That being said, I almost always wear an unlined sheer or lace bra or bralette under my shirt. Even if I'm not sure what direction the date is going to go in, I like knowing that I feel sexy and not too fussy underneath my clothes. —Tiffany Yannetta, shopping director
A black dress I bought at Forever 21 for $9 about five years ago and still looks perfect. Plus, I can spill just about anything on it. — Polly, New York
I usually wear dark skinny jeans paired with high-heeled boots, because my butt looks great in tight pants and the heels make me look slightly longer and leaner. If I don't want to look like I'm trying too hard, I wear Converse sneakers.
What I'm wearing on top depends on the season and where we're going... usually some sort of flowy, sleeveless shirt. I feel like it's a good halfway point in between casual and dressy. However, on my first date with my significant other, I wore a Madewell flannel over an American Apparel tank top. Not really my go-to, but it worked! —Ali, San Diego
Probably a dress shirt (with a tie if I feel like), dark jeans, and this amazing black SNS Herning cardigan. This is actually what I'm wearing tonight to a Valentine's Day singles event thing... —Ron, Toronto, CA