Picking Out A First Date Outfit: What To Wear & What To Avoid

You finally bag a date with that super hot person you’ve had a crush on for ages and you have plans for Saturday night. You’re ridiculously excited, but there’s just one problem: You don’t know what to wear. If you’re struggling when it comes to picking out an outfit for your first date, don’t freak out. We have the lowdown on what kind of clothing you should wear the first time you meet up and which items you’re better off skipping.

What kind of outfit should you wear on a first date?

When it comes to picking out the best clothes for your first time out with someone new, there’s no one set answer. That’s because this changes depending on what you’re doing on your date. For instance, if you’re going for something adventurous, such as visiting a climbing wall or going on a hike. you won’t want to wear a dress. In addition, the time of day you’re having your first date determines the best first date outfit.

Assuming you’re going on a standard date for dinner or to a local bar one evening, there are some general guidelines that you should follow to guarantee you make the best possible impression on your new love interest.

For women, this could include:

  1. Jeans or tailored slacks While you probably want to leave your well-loved pair of ripped Levi’s from six years ago at home, jeans can absolutely work for a date. Make sure they fit well and are a bit more dressy than casual. If jeans aren’t your style, you can’t go wrong with a pair of tailored trousers. They look super smart without being overly formal.
  2. A button-down shirt or blouse While you don’t want to just pick out one of your work tops from the closet and turn it into your first date outfit, do go for a smart shirt or blouse with your jeans or slacks. This ensures that your look errs on the side of casual while still looking like you made an effort.
  3. A little black dress, maxi dress, or skirt with top If you’re more comfortable in feminine clothing, there’s no reason you shouldn’t put on a cute dress or skirt for your date. This can be anything from a sundress or maxi dress in summer to a corduroy or velvet skirt with tights if you’re giong out during the colder months.
  4. Heels or flats — your choice Don’t feel pressured to pair your first date outfit with heels if that’s not your style. If you do love rocking a pair of stilettos, more power to you. (However, you may want to rethink this if your date is already much shorter than you.) If you’re someone who generally always wears flats, stick with that. A nice ballerina shoe, loafer, Oxford, or other flat will complete your outfit.
  5. Your choice of jewelry There’s no need to turn up the glitz and glam the first time you go out with someone. In fact, you should avoid overaccessorizing, as this can detract from your overall look. Embrace the idea that less is more when it comes to the jewelry you wear. One or two statement pieces can make all the difference.

For men, aim for:

  1. Well-fitting jeans or chinos This is gentleman’s choice based on what you’re most comfortable wearing. If jeans are more your style and the occasion calls for it, go with a nice clean (and maybe even ironed) pair. Otherwise, chinos or black trousers will work just fine.
  2. A button-down shirt or polo While you don’t want to look like you’re going to a funeral or a board meeting, you do want to look presentable. Pairing a button-down shirt can make your look seem more fun and relaxed. Feel free to choose a shirt with stripes or a light pattern. And, if your shirt has been hanging at the back of your closet or shoved in a drawer, don’t forget to iron it.
  3. A nice watch Clothing isn’t the only thing you need to consider when going on a first date. A nice statement piece such as a watch can really complete your first date outfit. It doesn’t need to be flashy or over the top, either. Choose something simple
  4. Basic dress shoes such as Oxfords or loafers It makes no sense to put effort into what clothing you’re wearing on your first date, only to ignore what’s on your feet. Choose a pair of nice shoes to go with your outfit to complete the look.

What clothing isn’t appropriate for a first date?

  1. Sneakers It goes without saying that unless you’re going to do something outdoors/something sporty, sneakers are not appropriate. Maybe on a second or third (again, depending on the activity), but leave your sneakers at home for date one.
  2. Sweatpants or tracksuits You’re trying to make a good impression. Turning up in your favorite raggedy sweatpants is not the way to do it. Again, unless you’re doing something active in which activewear is appropriate, don’t wear sweatpants or a tracksuit on a first date.
  3. Ratty t-shirts Just as with sweatpants, there is such a thing as being too casual. Ratty t-shirts are for lying around on the couch on the weekend. They’re not for trying to get to know someone new. T-shirts in general should probably be skipped, particularly graphic tees.
  4. Formalwear of any kind Just as you can be a little too casual, you can also be too dressed up. It’s a first date, not a wedding. This means you shouldn’t wear evening gowns, ballgowns, tuxedos, or anything too sophisticated. Otherwise, you could alienate your date.
  5. Wild prints or “loud” clothing items There’s nothing wrong with expressing your personal style. However, dressing too outlandishly could turn your date off or overshadow them, which is the last thing you want to do. Choose an outfit that’s representative of your personality but not too wild.
Bolde has been a source of dating and relationship advice for single women around the world since 2014. We combine scientific data, experiential wisdom, and personal anecdotes to provide help and encouragement to those frustrated by the journey to find love. Follow us on Instagram @bolde_media or on Facebook @BoldeMedia