what to wear on a first date
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Trying to figure out what to wear on a first date is one of those dilemmas that sounds trite but often causes a lot of anxiety. The challenges to knowing what to wear on a first date are nothing to dismiss out of hand. Every single girl who’s had to dress for a first date – and let’s face it, that’s nearly everyone – knows the anguish and chaos that arises from choosing that first date outfit.

The Importance of Getting It Right

First impressions count big on a first date. This is especially true if your first date is also a blind date. If your first date has seen you before, like when they asked you out on the date, they already saw you wearing something. At least, we presume this is the case. Unless he asked you out on a nude beach, which means he has quite the gall. If you were at work, or just stopping off from work on your way home, your date probably saw you in your fancy office attire. That first impression of you will stick in his mind, and he’s going to be expecting something maybe more formal for the first date. If you work as a garage mechanic, you pretty much have no place to go but up as far as figuring out what to wear for your first date.

The other reason it’s important to get it right is that he might be already seated when you arrive for the date. This is the case if you’re meeting him someplace, like a restaurant or bar. Two things are happening here. One, he has nothing else to do but look you and your outfit over while you walk toward him. Seriously. He can take his leisurely time mentally critiquing every little detail of you. Scary, right?

Two, while he’s been sitting there, he’s had nothing to do but watch every other woman arrive for their dates. There may be a part of him that’s going to compare you with all the other women he’s seen that evening. But try to put that out of your mind, because if this date works out, he’s probably going to do that every time you go out.

Why It’s Hard to Figure Out What to Wear on a First Date

Figuring out what to wear on a first date is really, really hard. For starters, you and your new date don’t have an apparel synergy going on yet. You could be totally out of sync. For all you know, this guy could show up in torn jeans and sneakers, with a knit hat topping it all off. That’s awkward when you dressed in stilettos and your best come hither slinky red dress. Or, you could dress in your conservative navy blue shift dress and kitten heels, while he’s all decked out Brazilian disco style. Unraveling the mystery of what to wear on a first date is a conundrum wrapped in a riddle.

The Dos and Don’ts of First Date Apparel

These dos and don’ts of first date apparel will get you where you need to be as far as the process of elimination. If the outfit breaks any of these dos and don’ts, leave it hanging in the closet.

Do wear something comfortable. If you spend the evening pulling and tugging at your clothes he may think you have an issue.

Don’t buy new for a first date. If it bombs, you will have wasted your time and your money. A double whammy.

Do ask where you’re going. Leave the surprises for the first anniversary dinner.

Don’t change outfits after you see what he’s wearing. Making him wait is kind of rude. Anyway, you won’t want to leave this veritable stranger alone in your living room while you change.

Do bring a coat, a jacket or some kind of wrap. The last thing you need is goose bumps popping up on your arm.

Don’t wear shoes you can’t walk in. A long romantic walk home is the perfect ending to a perfect date. You don’t want to ruin it by complaining about your bunions.

First Date Apparel for Every Situation

Depending on where you go for your first date, you’ll want to have an idea of what to wear.

Dinner and a Movie

For something this casual, nice slacks and a blouse is just fine. A dress could work for the dinner, but at the movies, it’s a little out of place. An exception might be if the night is warm and you choose to wear a sundress or a casual skirt and blouse combination.

Drinks and Dinner

Definitely break out the dinner dress and heels for this scenario. If you’re going to be sitting at a bar with your legs crossed, you want your legs showing, not your pant legs and socks.

Weekend Lunch Date

This kind of situation is easier to know what wear on a first date. Your ensemble should be upscale casual. If you’re the preppy sort, you could rock a cute pair of pants with colorful sneakers and a cardigan/knit top combo. Or you could go all athleisure wear and break out your yoga pants – as long as they aren’t see-through.


If your first date is a breakfast meetup, you’ve both probably talked about jogging or crosswords or something. Most first dates aren’t breakfast dates. But if yours is, feel free to pull your hair in a neat ponytail and wear cute active wear. Your date will probably do the same, sans the ponytail.

Errand Date

Did this guy actually have the nerve to ask you to run errands with him as a first date? Uncool. Don’t bother figuring out what to wear for this date, because it doesn’t matter. It’s probably going to be the last time you see him; if you decide to go through with it, that is.

What about you? Do you have trouble figuring out what to wear on a first date? How did you solve it? Let us know in the comments below!