What to Wear On a First Date

Whether you’re dating to find ‘Mrs. Right,’ looking to have a successful casual dating experience, or just looking to have some fun… choosing what to wear on a first date is a critical step. Obviously, you want to dress to impress—but you also want to be ‘you.’ It is common knowledge that first-impressions are formed within the first few seconds of meeting someone new—but new research suggests that you might not have as much time as you once thought.

According to psychologicalscience.org, a series of experiments by a couple of Princeton psychologists has shed light on the fact that it only takes a tenth of a second to form an impression of a stranger… and that longer exposures do not necessarily change our minds!

This makes first impressions more crucial than ever—which, in turn, makes your wardrobe choice on the first date a very important thing to get right.

But what exactly should you wear?

Let’s start at the beginning and dispel some common myths first.

What You Don’t Need to Wear

A lot of guys in western culture and society have a problem with personal style. They get used to shopping at large retail stores, buying gym shorts and budget-graphic Tees, and wearing basically the same thing all the time.

In other words, a lot of men don’t put a lot of effort into their appearance. That, or they hyper-focus on it in the short-term but neglect it in the long-term. In other words, they never think about their appearance until they score a date. And then, they spend the afternoon before trying to piece together something to wear… oftentimes without knowing what they’re doing.

A well-dressed man is a confident man—and this confidence will show. Because subconsciously, dressing well is sending a lot of messages to the people around you.

And contrary to popular belief, you do not need to wear designer clothes, or even expensive clothes, to look good.

Our style symbolizes who we believe we are as a person. And people really do pick up on this. So if you always dress sloppy on your first date? Well guess what—you are absolutely telling the world that you are a sloppy person with the way you dress!

They say that clothes make the man—and that is actually kind of true, at least where first-impressions are concerned.

Some men might complain that focusing on their looks is too vain. They may also rationalize away the need to take responsibility for how they look based on the idea that they want a girl to like them for who they are—not for how they dress.

But this is honestly a cop out. Men, we want our women to look hot—so we should put effort into being hot as well.

And that starts with how we dress.

What to Wear On a First Date: Ditch the T-Shirt and the Hoodie

Yes, there are situations where a T-shirt is not necessarily a terrible choice. If you are going to a baseball game, it may even be ironically appropriate. But even so—the vast majority of women favor a man in a button-up over a man sporting a sporty Tee.

If you are planning your outfit and dressing casual, try swapping out your T-shirt and wearing a button-up instead. Polos can be another potential substitute, but it can also be really easy for polos to look trashy—so we definitely recommend a button-up. A nice solid neutral-color does wonders, but a trendy plaid, or even a flannel, is also really in-style right now.

And where hoodies are concerned—just don’t. A hoodie is awesome if you are working out in the cold, lounging around the house, working outdoors, etc. It can even be a handy option to throw on while making a quick grocery-run.

But for the love of all things good and holy—do not wear a hoodie on a first date. Ditch it and go with a tailored blazer, a bomber jacket, or a leather jacket.

Leather jackets are actually really in-style right now, but they have to fit well. Blazers are a bit more forgiving, but there is also no excuse not to have a tailored suit coat on-call in your wardrobe for when a lady agrees to meet you for a drink on short notice.

Casual is Great for the First Date

When you ask us what to wear on a first date, you might expect us to tell you to dress-up a few notches. After all, first impressions are super important. But while we do want you to look your best, we also want you to know that there is such a thing as overkill—so the first time you get together, wearing a full-fledged suit, or tux, may not always be the best choice.

Obviously, this sort of depends on where you plan to go. But for the most part, keeping things nice and casual for the first get-together can be a great way to break the ice and create a positive first-impression without putting a lot of pressure on her to look a certain way (trust us… if she is into you, she will be pressuring herself already as it is!).

So with that being said, don’t be afraid to plan a more casual first-date. Hitting an art gallery, strolling through a museum, going to a coffee shop, or grabbing a drink at a cocktail bar can all be awesome first-dates that call for more casual clothing.

You can wear nice-fitting jeans, or even slacks for a date like this, along with a nice button up and some attractive boots or clean sneakers. Accessorizing with a nice watch never hurt anything, and a bomber jacket, a casual blazer, or even a leather jacket can help to complete the look.

You might be able to get away with a T-shit if you wear it under your blazer—but be weary of this in warm weather, because you might be tempted to take off the jacket—and wearing just a Tee on a first date is simply lazy.

See what Jo thinks!

How to dress up on the first date? — Wear clothes that accentuate your best features. Dress for where your date is gonna be. Movie Date? Go casual. Dinner at a fancy restaurant? You can’t wear shorts to that. Be smart about what you’re gonna wear. https://t.co/kyLl2naTiM

— jo (@carmelmachiatow) October 25, 2018

But if you do plan to wear a T-shirt under your jacket, opt for a V-neck instead of a crew—and NEVER go graphic! It’s just cheesy.

If you are meeting for dinner, or going to a fancier speakeasy—well, that is a different story. For these types of occasions, don’t be afraid to dress up—but be careful not to overkill it either.

Unless you are going to a wedding or walking her down the carpet at the Oscars, a tux is usually going to be too much.

A pair of tailored dress pants, with a complimenting button-up, is almost certainly going to be the way to go for a fancier first date. Jeans with a button-up and a nice tailored sweater can also work, but be careful about jeans and nice dates. It can send a very sloppy/lazy vibe if you don’t pull it off just right.

Nice shoes and a matching suit-coat or cashmere coat can really help to compliment this look. Leave the sneakers at home for a fancy date like this! Opt instead for a pair of nice shoes, dressier boots, or even loafers.

But whatever you do, you should never…

• Show up in flip flops
• Show up wearing toe-shoes (Google them… they are gross)
• Show up wearing Crocs (Just no)
• Show up wearing a sports team jersey (unless you are going to a game—and even then, not the best move for a first date, my friend)

Above All, Make Sure Your Clothes Fit You Well

One constant that a lot of people seem to forget is that a good fit often trumps a high price-tag. You can wear the most expensive suit on the market—but if it is baggy, or fits too tightly, or if it doesn’t fit your body right in the proper places, it is just going to look sloppy—end of story.

You want your clothing to fit you right—and that means putting more effort into your wardrobe beforehand.

Try on clothing before you purchase it. Check for a good fit. Is it long enough? Is it loose enough without being baggy? Does the collar fit around your neck with a little room to spare?

Do the pants fit comfortably, but also look slimming?

Baggy clothes are a no-go in pretty much every first-date scenario. The same is true of clothing that is just plain worn, old, tattered, or out of style.

But please, do what you can to wear clothing that fits your body well. It is also important to get your clothing tailored, even if the adjustments are small. This can do absolute wonders for how it will end up looking on you when the time comes to create a great first-impression.

This is especially true of body types that are kind of ‘between’ traditional sizes.

Is a large usually a bit big on you, but a medium almost too small? If you are in a category like that, it is almost always a good idea to get your button-ups, pants, and suits tailored to fit you well.

You certainly don’t have to spend a fortune to make yourself look good. But you do have to put effort into it.

The best rule of thumb is to get your wardrobe ready now, picking up new pieces every couple of weeks, or months, to slowly fill out your different clothing options so that you will have some different things to pick from when the time comes to get dressed up. Knowing what to wear on a first date is critical if you want to score an awesome first impression. So take it seriously, and put some real effort into it now so that you won’t have to stress about it later.