Nervous about what you’re going to wear on a first date? This article will help you choose the right outfit.
First dates are nerve-wracking. Even guys who have been on a lot of first dates can still feel anxious about them.
There’s a lot to think about. What are you going to say? Where are you going to go? And, of course, what are you going to wear?
If you have no clue what to wear, you’ll feel even more nervous, and you’ll probably end up throwing something together at the last minute. And sure, you might be presentable, but it’ll likely be obvious that you rushed things.
Knowing what to wear on a first date is crucial to making a good first impression, and assembling a good outfit will take some planning. However, when the time comes for you to meet your date, you won’t be sweating trying to decide which crumpled shirt you should wear.
So let’s get to it. Here’s our practical guide on what to wear on a first date for guys.
Table of Contents
Things to Consider
Before you even think about your clothes, you need to think about your actual date situation. There are many factors that can affect what you wear, and that’s where some planning will help.
Consider the Other Person
You don’t have to overhaul your personal style just for your date, but considering their tastes will likely come in handy. For example, if they tend to wear more casual, sporty clothing, then you might want to add a preppy touch to your outfit.
Dress Right for the Location
The actual place you’re meeting is going to have a huge effect on your outfit. You want to match the formality of the location (at least approximately) so that you don’t look out of place. If you’re meeting up at a bar and show up in a two-piece suit, things might get a little awkward.
Think About Time of Day
This is another big factor. If your date is in the daytime, then you’ll probably want a more casual outfit. Generally, nighttime dates call for a slightly dressier look.
This ties into location. Daytime date locations (casual restaurants, coffee shops, parks, etc.) are typically more casual than nighttime locations (fancier restaurants, clubs, etc.). Of course, this isn’t a rule, so considering the location is still important.
What Not to Wear on a First Date
Before we look at what to wear on a first date, let’s look at what not to wear. It’s easy to make mistakes, and you don’t want to be the guy who makes a fashion faux pas on the first date.
Hoodies. Hoodies are great for casual get-togethers, but if you wear one on a first date, you’ll just come across as lazy. Instead, layer if it’s cold out. A bomber jacket over a button down shirt looks much better than a hoodie.
Sweatpants. See above. For colder weather, try a pair of thick cotton chinos.
Graphic T-shirts. As much as you might want to rep your favorite artist or TV show, that’s not a look you want to be sporting on a first date. (One possible exception here is if you’re going to a concert, but even then, consider pairing it with an unzipped jacket.)
Ties. Ties are a bit too formal for most dates and can make you look too corporate. Unless you’re going to a red carpet event, ditch the tie.
Sandals. This one’s self-explanatory…right?
What to Wear on a Casual/Daytime First Date
Now that we’ve gone over some basic date outfit etiquette, let’s look at some of your clothing options if you have a casual or daytime date.
Oxford Cloth Button Down (OCBD) Shirt
The trusty OCBD shirt is an excellent choice for a lot of first date scenarios. It’s classy but not pretentious, and it communicates that you put thought into your appearance.
A flannel shirt (like the one on the right) is also a solid option, though it’s a tad less formal.
If it’s going to be really hot out––or if you just live in a really warm climate––consider a linen button up instead. Linen shirts are thinner and more breathable than OCBD shirts, but they look every bit as nice.
While many guys associate polo shirts with the preppy frat look, they’re actually quite versatile. A polo is a good choice if it’s warm enough out for a T-shirt but you want something a bit nicer.
Polos with lots of branding can be distracting, so go for a nice minimal polo in a neutral color like navy or charcoal. In addition, opt for a pique knit polo instead of a jersey knit. Piques are more textured and look less sporty.
Full disclaimer: T-shirts aren’t appropriate for every kind of date. And most of the time, you’ll want to layer if a t-shirt is central to your outfit. But a simple t-shirt can go a long way.
If it’s summertime and you have a daytime meetup planned, then a fitted (but not too tight) t-shirt can look great when paired with some nice trousers and shoes.
If you need to layer, no problem––there are lots of great outfits you can build around t-shirts. And if you want to stand out a little more, choose something like a v-neck or a henley instead of the classic crewneck.
Chinos are some of the most versatile pants you can buy. They’re great for any casual situation, and you can even dress them up for business casual settings.
Chinos are nice for first dates because they go with just about any outfit. Basically, it’s hard to make chinos look bad.
Chino shorts are also an option if you need something breezier, but only wear shorts if you're on an outdoor warm weather date.
Casual First Date Outfit Ideas
Now that you know which articles of clothing are best for daytime dates, let’s look at what to wear on a casual first date.
#1: Button Up Shirt with Jeans
For more casual daytime dates, throw a button up shirt over a t-shirt for a relaxed yet refined look.
If it’s a slightly crisper day, you can button up your shirt but leave the top button undone for a casual touch. (You can also do this if you just don’t like the look of an unbuttoned shirt.)
This is a really flexible look that will work well for just about any kind of daytime date. Avoid jeans with a light wash and lots of distressing, though.
There’s nothing inherently wrong with lighter jeans, but they can tend to make you look like a 17-year-old who shops at Abercrombie & Fitch.
Darker jeans give off a more mature vibe.
#2: Polo Shirt & Jeans
This outfit is simple and straightforward: a polo, jeans and
Again, minimalism is the key here. This polo has no visible branding, and it’s a deep navy that matches most outfits. The jeans and shoes don’t draw any unnecessary attention to themselves, either.
It can also help to accessorize. For example, tossing a watch and bracelet into the mix as shown here can add some nice detail and tie your outfit together.
#3: Henley & Chinos
Another simple, understated look, this outfit is based around a nice navy henley and some olive chinos.
The colors complement each other nicely, and the
Be sure to not wear shades indoors, though. 😉
What to Wear on a Formal/Nighttime First Date
Like I mentioned earlier, if you have a nighttime date planned, chances are the atmosphere will be a little fancier.
You’ll also probably need at least a little extra warmth. With that in mind, here are some garment choices for evening and nighttime dates.
If you need a bit of warmth (or just another layer), opt for a jacket.
There are many jacket types to choose from, but you could argue that the Harrington is the best all-around jacket.
The Harrington is lightweight yet structured, and it can be dressed up or down. Most Harringtons have patterned linings that look great when you leave the jacket unzipped. It adds a ton of depth to your outfit and gives the impression of an additional layer.
You could also go with a classic leather jacket if your date is more casual, but a Harrington is way more flexible, so it’s a safe bet. If you’ve been wondering what to wear on a first date for drinks, you should definitely consider including a jacket.
For a more formal look, consider a tailored blazer.
Blazers are often seen as more formal, but you can also dress them down by incorporating them into a smart casual outfit. The formality of a blazer depends on its color and fabric.
You can wear a blazer over an OCBD or dress shirt for a smart casual look. If it’s colder out, exchange the button up for a sweater or wear a sweater over your button up. Either way, you’ll have a snazzy layered outfit.
Need I say more? Sweaters are perfect for colder weather, and you can layer them with just about anything for a dapper look.
The classic combo is, of course, a sweater over a button up, but there are tons of styling possibilities.
Chinos work well for a lot of first date environments, but there are some instances where you’ll want to upgrade your pants (for example, if you’re heading to a fancy restaurant).
In these situations, a pair of wool or linen trousers will do the trick. Go for a basic/neutral color like black or grey.
Of course, if you’re not heading to a five-star restaurant, then a nice, ironed pair of chinos will probably be fine. The important thing is to choose clothing that matches the formality of the occasion and venue.
Dress Shoes or Boots
When it comes to footwear, it’s always safer to err on the side of formality. That doesn’t mean you should rule out
How fancy do you need to go? If you have a pair of Oxfords, those are definitely formal enough for a nighttime date.
In fact, depending on the date, they very well might be too fancy. Going down a few notches on the formality scale, you have loafers and boots.
If your style is somewhat preppy or sporty, then loafers might be a good choice for you.
Boots are a little more versatile––you can choose from a wide range to suit your needs.
Finally, when it comes to
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Formal First Date Outfit Ideas
Dressing up can be tricky, especially if you’re not used to it, so let’s look at some simple formal outfits for first dates.
#1: Harrington & Chinos
If you have a nighttime date that’s more casual than formal, you’ll want an outfit that’s refined yet not stuffy.
Pairing a Harrington jacket with chinos gives you that “put together yet laid-back” vibe that can be hard to achieve.
The jacket will provide you with a bit of warmth if you need it, and it looks great over any type of OCBD shirt. This look is great for a lot of first date situations.
Don’t know what to wear on a first date to dinner? Try this. Grabbing coffee? This outfit is perfect for that, too.
#2: Smart Casual Sport Coat
For a great smart casual look, toss a sport coat on top of a couple of layers. The jacket will elevate your outfit, but you can dress it down by wearing dark jeans and more casual shoes.
You can’t go wrong with a button up shirt, but a long sleeve polo will also work. Feeling fancy? Add a pocket square for a subtle splash of style.
#3: Quarter Zip & Jeans
Quarter zip sweaters are excellent for layering and always look nice.
Combine a quarter zip with jeans and Chelseas, and you’ve got a fantastic outfit that you can wear nearly year-round.
This outfit is a good choice for guys who have no idea of what to wear on a first date and who typically dress business casual throughout the week.
How about you?
Over to you now––what do you like to wear on a first date? Will you be wearing one of these outfits on your next date? Tell us below!