6 Date Outfit Ideas — From Casual to Formal

You’ve got a romantic evening out on the town (or in on the couch), and you want to look the part. Obviously, you don’t show up to movie night at home in a ball gown, nor do you show up to the opera dressed for racquetball. Those two pieces of information, while obvious, do leave a little something to be desired. If you’re not sure where to start, we’ve got some help to offer.

  1. Taking a Hike

Really, this is best reserved for those who already have been dating a bit. It’s not a red flag if this is a first date but maybe file it away for later pondering.

Athleisure is your friend here. If it is or looks like it is Lululemon, it’s a go. Maybe not the bright-colored ones, but you can if you like. That’s about it.

Avoid: Dressing too casually. Yeah, it’s a hike, but still. Just do your best on this one. It’s a tough spot to be in. Make sure you’re wearing proper hiking shoes at the very least.

Dress It Up: If the weather is cool enough, maybe an athletic quarter zip? Again, this is a tough spot. Just make sure to plan accordingly and you won’t have anything to worry about.

  1. Why Don’t We Just Walk?

This is the peak of casual without too much sweating. You want to look nice, but you’re just strolling aimlessly from point A to point B, so the requirements for formality are low.

Consider some nice jeans and a decent shirt. While that sounds vague, it’s really all you need to know. Whether you want a short sleeve button-down or a casual blouse is your call, but just pair something with jeans and some casual shoes. If you want to be a little more dressed up, a couple of pieces of simple everyday jewelry works wonders.

A sundress or something similarly casual will work here, too. Gents, shorts are fine if they’re nice chino shorts. If you’re unsure whether they are, they probably aren’t.

Avoid: Anything that toes the line of athleisure. If it’s more ath than leisure, skip it.

Dress It Up: Dark denim instead of light and some boots, weather permitting. Maybe some nice sandals if the weather is too warm for boots.

  1. The Coffee House

We’re going to spoil the ending: this one is very much like the last one. There is, however, a key difference or two.

Like the last option, you’re basically set on jeans and a good casual shirt. However, in this scenario, maybe dress it up just a tiny bit, depending on the coffee house you’re going into. If it’s one of those trendy places that stares at you blankly when you order regular milk, adjust accordingly. If “house” is spelled “haus” or the name is in all lowercase, it’s one of those places.

Jeans still work here, like the last one, but guys probably want to avoid shorts. Ladies, all the same applies here, but feel free to look for something more trendy if that’s the coffee shop’s vibe. One of those wide-brim hats that are popular now could be a fun accessory.

Avoid: Being too casual. You aren’t moving much or outside, so you don’t need to worry about being too warm. You don’t need to try too hard, but go at least one notch up from the last date outfit.

Dress It Up: Add a light jacket and a couple of cool rings.

  1. Dinner (Optionally, a Movie)

This is a classic date night occasion, and what to wear mainly depends on the restaurant. If the restaurant is casual, see our last idea. Let’s assume the restaurant is a touch nicer than the coffee shop. What then?

Take the ideas from the last one and rework them. Go with darker colors for a nicer casual look. Dark denim works well here, as do some types of trousers. If you’re going for trousers, you have more leeway on the color. For more casual settings, a chunky sweater works well. In nicer settings, a more minimalist sweater or even a leather jacket bridge the gap of casual and semi-formal. Guys, all the same rules apply.

Avoid: Being underdressed. Look, don’t go overboard. If you’re on the fence, it’s better to be a tiny bit overdressed than a bit underdressed.

Dress It Up: Dressy casual shoes. Wedges, brogue boots, anything like that.

  1. No, They Call Them Mixologists Here

You aren’t going out to a dive. This is a cocktail bar with a “proprietary cocktail list” and “mixologists.” Yeah, they’re a little pretentious, but they’re also fun. Bonus: they usually do have great drinks.

If you like being on trend, this is where you shine. Dark denim or trousers are great again, but this time, go for a shirt with buttons. Something that’s fun. This, of all the options, is probably where you have the most room for creativity. For a really nice cocktail bar, black dresses and dress pants with semi-formal button-ups are the way to go. Dress shoes or heels to match, and you’re set.

Avoid: Being underdressed. This one is the same as the last. If you’re unsure, look the place up and get a sense ahead of time.

Dress It Up: More formal dresses or casual suits (jacket included) are great for upscale cocktail bars.

  1. Gatsby Would Almost Be Impressed

The formal date. Whether it’s a gala of some sort, a wedding or anything you’d need to wear your best formalwear to, you’re there. Maybe it’s a charity event. Maybe a halo engagement ring is going to be the star of the show.

Formal gowns are great here with heels. If you don’t want to go all that far, a black dress in a mid-length style always works. Whatever you think of when you think of classic formalwear, operate in that vein. Guys, you probably don’t need a tux, but a suit is a must. Dark navy or gray unless you’re required to wear black.

Avoid: Anything truly uncomfortable. Yeah, it’s formal, but if you don’t love it, it’s just not going to be the same. Beauty is pain and all, but like, maybe not?

Dress It Up: You’re pretty much at the peak. Maybe a statement necklace or some nice cufflinks if you need more depth to the outfit.

These aren’t strict rules. More like guidelines. If you’re putting together an outfit for an upcoming date, we hope these help, though. Good luck!