What To Wear On A Date

Look at both your own and your date’s personality and interests.

If you want to make a good impression, it’s important to dress appropriately—obviously, but choosing what to wear can be challenging! It helps if you know what your date is interested in. If they’re going to a concert, wear something representative of the band. If they’re taking you out to a fancy restaurant or museum, tone down how casual your outfit is. Remember: this won’t be the last time you see them; there will be plenty of opportunities for you to get comfortable with each other and show off your personal style later!

Also think about whether you’ll feel comfortable in your outfit. You don’t have to wear something that doesn’t reflect who you are just because it’ll please your partner.

Don’t go overboard with fashion, though.

Please don’t get dressed up just because you think you have to. While your date may be wearing a suit and tie, that doesn’t mean you should wear a ballgown. If your date is wearing high-end designer clothes, that doesn’t mean you need to similarly buy expensive clothing items. Your date’s expensive jewelry doesn’t mean you should put on all of your jewelry (and worry about it getting lost or stolen). Your date might be wearing cologne, but please don’t go overboard with the perfume. It’s also worth pointing out that if your date is looking like they’re ready for Fashion Week in New York City, that does not mean you need to change into something uncomfortable for yourself. On the other hand, if your date has a pierced nose, green hair tips and combat boots, this does not give you permission to dress down from the level of comfort you normally feel.

You don’t have to dress up like you’re going to a three Michelin star restaurant on a date!

If you’re the kind of person who is always five minutes late, or who waits until the last minute to make dinner reservations, you’ll want to err on the side of overdressed. I don’t mean that you need to show up in stilettos and a ball gown for a trek through your local park (unless you’re down with that). But don’t wear your oldest T-shirt and flip-flops when there’s a chance you might end up at an upscale restaurant.

You also shouldn’t assume that your date will dress a certain way. If it’s been three dates already and she always has on sneakers and jeans, she might still surprise you on date four with stilettos and a pleated skirt. Conversely, if he wears business casual even when hiking, he might be saving his rock climbing shorts for something special (or maybe he just really likes to wear business casual). You can’t read someone else’s mind! It’s better to not be caught wearing something so formal it looks like you’re trying too hard; or so casual that it looks like you didn’t even try at all.

Make sure you can be yourself on the date.

So, what does that mean, in a practical sense? Well, first of all, don’t put on an outfit you wouldn’t wear to work or even in your own home. Sure, you want to look nice, but it’s more important to be able to relax and feel like yourself. If you’re going somewhere fancy and you’re not comfortable in fancy clothes, let him know beforehand that you’d rather go somewhere more low-key—and if he doesn’t agree with your approach to dressing up (or down), then maybe this is a sign that he isn’t the guy for you. Similarly, if he seems disappointed when you arrive wearing jeans instead of a dress or a suit instead of cargo shorts—well then again: Maybe this isn’t the guy for you, or at least the guy for right now. You should never feel pressured into wearing something specific for someone else’s benefit; yes it’s important to be considerate of your date’s wishes, but ultimately this date should make both people happy.

Just because you’re dressing up for a date, doesn’t mean that you can’t be comfy!

Dressing up? Yes! Feeling uncomfortable? No! Just because you’re dressing up for a date, doesn’t mean that you can’t be comfy. The key is to avoid clothes that are too tight, itchy, or otherwise unpleasant to wear for long periods of time.

  • Too tight: Do not wear something that presses uncomfortably into your skin. You should not have to adjust your clothing every five minutes (for example, pulling down a dress or shirt that won’t stay put).
  • Too lose: On the other hand, do not wear something so loose that it’ll get in the way of fun activities and interactions. For example, if you plan on going on an amusement park date where you’ll ride the Tilt-A-Whirl together and eat some cotton candy at a picnic bench, you don’t want to be wearing a floor length skirt with a train. While elegant dresses are beautiful and princessy, they are not practical unless you’re going to a ball or other fancy event.

Be prepared for any situation.

It is also important for you to be prepared for any situation. Here are a few essential things you should have with you at all times:

  • A spare pair of underwear
  • Mints or gum
  • Extra shoes (for an impromptu shift in location, such as a walk on the beach)
  • A wallet (to pay for activities and/or refreshments)
  • A jacket (to stay warm on a cool day)
  • A charger (so your phone doesn’t die), as well as a phone itself. It’s the modern-day Swiss Army knife; with one, you have access to something that can solve any problem. Some phones even come equipped with built-in Swiss army knives!
  • Towel(s). “A towel is about the most massively useful thing an interstellar hitchhiker can have,” says Adams. “Partly it has great practical value … [a]t its most basic, it can be used to drink out of.” Couldn’t have said it better myself. According to my own experience, though, I would add that towels are also useful for drying off after swimming or if it rains unexpectedly. We’ve already mentioned the neediness of Mother Nature; a date probably shouldn’t feel like an endurance test, so pack your towel accordingly!

A mini-kit of makeup is also good to carry around in case you decide to change up your look partway through the date.*

Don’t forget about the weather!

  • Date Weather: Because you don’t want to be too hot or too cold, this is a big thing to consider. Some things to keep in mind are the temperature and the type of date. When deciding what outfit to wear for your date, remember that it actually matters what the weather looks like that day and what the plan is for your date. If you go out on a dinner date on a sunny day, wear something light and breathable instead of bundling up with layers (like a sweater). If it’s pouring rain outside, opt for flat shoes over heels so that you don’t have to dress them with socks, which some people might find unsightly.
  • Overall Weather: When deciding what outfit to wear for your date, remember that it actually matters what the weather looks like that day and what the plan is for your date. For example, if you’re going out on dinner but it happens to be raining outside, then make sure you bring an umbrella so that you can arrive at dinner looking just as fresh as when you left home! Another thing worth mentioning here would be if it’s windy outside then maybe choose different shoes than usual – this could mean wearing boots rather than heels or flats instead of open-toed sandals (whatever works best for where your feet will end up getting wet most likely)

Once you’ve figured out some basics about how to dress for a date, it’s all about making sure you’re comfortable in your outfit.

Once you’ve figured out some basics about how to dress for a date, it’s all about making sure you’re comfortable in your outfit. This is especially important, because when you’re uncomfortable, it may stop you from being able to be yourself on your date. You want to make sure that what you’re wearing matches the location and the occasion as well. For example, if your date is at a fancy restaurant, you probably wouldn’t wear shorts and flip flops. Also, if it’s raining outside, maybe don’t wear a white t-shirt and shorts. If there wasn’t any weather or occasion information provided with the invitation for the date, just ask!

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