DRESS CODE: Choosing Cute Outfits That'll Help You Win Your Next Date Night

  • PublishedFebruary 16, 2018

Some people love getting ready for dates. They consider it the fun part! Not so for the rest of us. In our latest installment of Dress Code, we’ll help you execute an appropriate outfit for some common dating scenarios.


Some people like dating. More power to them. For many of us, it’s a stressful necessary evil made even more disspiriting by a wealth of “meet-your-soul-mate!” screeds that pepper the airwaves. But whether you’re trusting a friend, compatability points, a promising chance meeting or just fate, we all need to go on first dates sometimes, and it’s generally advisable to wear clothes. I polled a lot of friends on this issue and came up with a staggering array of approaches, from “I’ll wear my vintage majorette costume and if he doesn’t like me for me then he’s not worth it anyway!” to “I always buy a new outfit.”

Most of us fall somewhere between the two, wanting to look attractive but not trying too hard, hoping to balance expectation with excitement. Here’s what I can tell you for sure:

Wear your magical clothing

If you have something magical, wear it. You know what I mean: it might be a pair of jeans that’s good luck, or a shirt that makes you look awesome, or just a pair of shoes you associate with something good. Nothing – not the most expensive denim or most artful undies — is a match for something magical when it comes to confidence-boosting.

Don’t assume you need new clothes

If you really like wearing something new for a date, I guess go for it. Personally, I’m wary — it puts a lot of pressure on both the date and on you (to find something magic.) That said, if something novel makes you feel good, who am I to object? I am a great believer in new underwear — no, not because “someone might see it”, although, sure – but because you’ll have that sense of specialness conferred by newness, without the pressure. Plus, it’s kind of nice to have Underwear Without History (which has, oddly enough, never been used as an album title.)

I am also in favor of being both a borrower and a lender. Borrowing from a sympathetic friend whose look you like is like having an ally with you — plus, you get the sense of something different without the outlay or the pressure. NB: I am talking about consensual borrowing, not “stealing.”

If you feel like you need something new to give the event sufficient occasion, sometimes splashing out on a little grooming — say, a manicure or (a few days prior) a facial — scratches the itch. It’s a nice confidence boost (or maybe that’s a curly-haired thing, because you never feel like your grooming is completely within your control.)

Be Comfortable

This should, I hope, go without saying. Painful shoes and jeans that dig into your stomach are not sexy. You want to be able to walk, sit, and eat without thinking about it.

Look Like Yourself

Another “duh,” maybe, but a first date is not the time to try out a new persona, no matter how cool Brigitte Bardot looked in Contempt.

Bring A Sweater.

You might get cold.

Oh, and Practice Sitting Down.

Some things get really low-cut when you’re sitting. This can be awkward. You’ll end up tugging at your neckline. Trust me on this one.

Have a “Confidence Soundtrack.”

No joke, I have a playlist on my computer entitled “Confidence Dressing.” It’s what I play when I’m feeling shy and apprehensive and need to amp myself up. I always play “I Touch Roses” by Book of Love last, so I feel extra-sassy when I walk out the door.

Now, let’s get down to brass tacks!


This can mean a lot of things: brunch, a picnic, a museum, an outdoor concert, a daytime movie, coffee…you know the drill. These dates tend to be cheap and casual, so the idea is to dress as you would normally – except you happen, normally, to look completely awesome and effortless.

These are, obviously, natural jeans events. If, like me, you aren’t a jeans person, a print dress is a good alternative. In general I think a good rule for looking casual-but-not-shleppy is “Balance.” If you’re wearing a dress, throw on a denim jacket. Doing jeans? A blazer or a non-sneaker polishes it right up. Don’t sweat being sexy. While I stand by “being yourself,” I also don’t think it’s wrong to put on your confident persona when you walk out the door — yes, the music helps. Oh, and always pack that sweater — movie theatres are cold.


These are tricky. First things first: do your due diligence. Find out how fancy the restaurant is. Being underdressed is always preferable to being overly fancy, but it’s not wrong to make an effort. If you’ll be coming from work — and if this means your date will be in a suit — take this into account.

Here, more than in any other situation, I believe in plying the “balance” rule. Wearing jeans? How about a heel, or a hunk of jewelry? Going with a dress? Make it a casual one, or throw on flats or a low-key jacket, denim or whatnot. (I am, I think it is obvious, a great believer in print dresses: they can be cheap, and it takes out a lot of the guesswork.) For dinner dates, as a rule, I’d say avoid sneakers. Carry a grown-up purse. Don’t wear silk, unless you’re a really neat eater. Make sure your clothes allow you to eat. And here, more than anywhere else, do the sit-down test. I cannot stress this enough. The cleavage is totally different than when you’re standing. Once again, carry a sweater: you might get stuck with the door table.

The Active Date

Maybe you’re on some MTV dating show where you have to do something crrrrazy like play paintball or throw water-balloons at each other or do finger-painting. Maybe you’re bowling or going to a batting-cage, because a date isn’t stressful enough already! Maybe your date has something “creative” or “whimsical” planned and has just said “wear walking shoes.” I hate these dates.

I’m not saying I didn’t enjoy climbing that 15-foot fence and trespassing into that abandoned Grecian structure in Prospect Park so we could catch fireflies and hear the “amazing acoustics,” but I still kind of hold it against my now-fiance that I ripped a perfectly nice and surprisingly overpriced Built by Wendy dress. (At the time, of course, I had my “up-for-anything good sport” face on, so I pretended I didn’t care at all.) So let’s think of this as your “Good Sport” costume.

This is when, yes, you’re probably going to need jeans. And comfy shoes. Gym glass-style, avoid dangly jewelry (although I wouldn’t go so far as taping it to your chest.) But there is no need for looking like a schlep: keep things relatively fitted (as opposed to tight) and bring on the patterns. I’m also a fan of a jaunty kerchief, but that’s me. You want a bag that’ll go over your shoulder and things that don’t need to be dry-cleaned. And, yes, hair out of your face.

The Fancy Date

Maybe you’ve been asked, strangely early on, to be a wedding date. Or go to a cocktail party. This will be tricky because, absent of the physical invitation, it will be very hard to determine the level of formality required. Some might say “LBD,” but I say, go “gently quirky.”

I’m not saying be the wacky chick in the vintage prom dress, here. Mix basics with contrasting shoes, or a bag. This looks confident and fashion-y and people will assume you know what you’re doing. Also, this will allow you to err on the side of slightly-underdressed which is, as we know, better than the alternative. A belt can do wonders. As can something in one’s hair. (Dodai is, obviously, the master of this: she owns the flower.)

The Group Date

Perhaps the most tricky of them all! This can be any number of things, from a bash at someone’s house to a dinner party. Either way, it involves meeting people you don’t know, who could be arch-hipsters or fashionistas or jerks or awesome or all of the above. There’s really no one formula for these profoundly stressful situations: my advice is be yourself, amped up.

More than any other time, you’re going to want to feel comfortable. You won’t be shocked the hear that, as usual, I advocate a balance of smart and casual, and that I personally go for a print dress, black tights, and some easy jacket. You will have your own uniform, but I would say: don’t bother trying to blend in or be the stand-out in the miniature hat (which, yes, I have done.) Just be the you that you want to be when your confidence-dressing song is playing. Here are a few ideas that I think are appropriate for just about any of these situations, but obviously they won’t work for everyone.

You’ll get my point, though: basic shapes, made interesting – or basic outfits enlivened by a personal accessory. You don’t want to have to think about what you’re wearing — but when you happen to, you should feel good.

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