How to Dress for 5 Different Types Of Dates

Last updated: December 26, 2021

Wherever you’re going for a date, it’s important to show off your best self without looking like a try-hard or deviating from your personal style.

First impressions, your appearance, your presentation matter but your outfit should reflect your personal style.

#1 Dinner Date

You can’t go wrong with a proper dinner because food is what brings people closer. For a casual nighttime dinner, or a typical date night, you can show your date your everyday style with a little effort in order to look sharp.

Opt for darker colors as they seem to add a more classy and sophisticated vibe. Style a black turtleneck with black trousers and Chelsea boots adding a red flannel shirt on top.

Don’t be afraid to integrate a pop of color into a monochrome look, in this case, red is an emotional color that goes perfectly with black.

Try to match with your dates outfit, because you know she will also be looking extremely stylish for your date- and we have some inspiration outfits for her so you both can try coordinate, and even have a cute instagram picture ready.

If you’re planning to go with your date to a fancy restaurant, your everyday getup might not be appropriate for this occasion.

The key is to be formal enough for the venue and to make it look like you’ve actually made an effort.

Mix traditionally formal pieces like a baby blue striped oxford shirt over a white t-shirt, smart trousers and a wool black coat on top.

For shoes, you can either wear Brogues or Derbies. Feel free to roll up the sleeves, to show a nice wristwatch or bracelet.

#2 Drinks Date

Another staple that you can always rely on it’s the classic ” let’s grab a drink’’ state.

Regardless of which bar you’re headed to, one proven way to stand out is to wear a pair of tailored trousers instead of classic denim jeans.

Style them with a plain t-shirt and minimal sneakers.

Pop on a lightweight bomber or a leather jacket on top and you have an outfit that feels sophisticated without being overly formal or casual. 

#3 Movie Date

If you’re gonna be sitting cramped in a movie theater for two hours, you might wanna reconsider the skinny fitted jeans.

Instead, opt for slim or straight-leg jeans for your own comfort. Pair them with one single jacket or coat as your outer layer to remove it easily as you are sitting.

Blue indigo jeans, a knit sweater and a leather jacket or an unstructured blazer will look great on you.

#4 Active Date

If you were to do an active date than your standard dinner, drinks or movies, you want to feel relaxed and cozy.

Either you’ll go for a walk, a picnic or to an art-exhibition, make sure you bring a comfortable pair of shoes like your fave sneakers.

Since you’re likely going to be outdoors for some part of the day, flaunt your outer layer.

Choose a wool plaid coat combined with pants and a t-shirt in earthy tones, that looks great with natural daylighting.

#5 Home Date

For a date at home, you can obviously dress more casual but that doesn’t give you an excuse to wear your fave sweatpants and hoodie.

A clean, neutral-colored t-shirt that fits well or cashmere knit with chino pants is ideal for this setting.

Make sure your sock game is on point, a pair of minimal, clean socks can make the difference.