Do you have a first date coming up? That can be really exciting, but also stressful. What on earth are you going to wear?
Many men make the mistake of not putting thought into their first date outfits. Sure, it’s great to show up “as yourself”, but you only get one chance to make a first impression. You can still be yourself while dressing it up a little bit.
If you’re new to the dating scene (or if you’re not and you just don’t know fashion) and you’re not quite sure how to dress for a first date, you’re not alone.
That’s why we’re here to help.
Keep reading for a few tips on dressing for your date.
Things to Avoid
First, we’re going to start off with how not to dress for a first date. There are a few things that just don’t work no matter what kind of date you’re on or who you’re meeting.
There are cases in which people won’t mind these things, but if you don’t know this person very well, it’s best to cover your bases.
All dates are different and some environments require different attire. Keep this in mind as you read this general list of “no-go”s.
Ripped Clothing
So there’s a way to wear stylishly ripped clothing. If you have distressed jeans or a shirt with intentional rips for style, that might be the perfect outfit for a first date at a bar or music show.
Otherwise, though, check your clothes for rips before you get going. It’s better to have a simple shirt without rips than a fancy one with rips.
Overly Political Clothing
On the one hand, it’s good to know where the other person stands right away. On the other, politics are divisive and this is just a first date.
While you may get into those deeper conversations, political shirts, hats, and other large and obvious items aren’t a tidy look and they may seem tacky to someone who’s just trying to come out for a good time and not a debate or analysis.
Poorly-Fitting Clothing
Sometimes oversized clothes are in. These clothes, while oversized, are intentional. It’s easy to see the fashion appeal.
Other times, though, an oversized shirt with baggy jeans is just a bad and lazy outfit. The same goes for clothes that are too small. You’re not doing yourself favors by shopping outside of your size.
You don’t need a tailored suit. Just try to look neat.
Athletic Clothing
Are you meeting at the gym or some kind of sports area? Disregard this section.
Otherwise, leave the basketball shorts, leggings, or muscle shirts at home. You’re not here to play the championship tournament, you’re here for a date.
A Full Suit
It might be tempting to completely take a 180 from your normal style. Maybe a suit will impress your new date!
Unless formalwear was agreed upon, a suit can seem overwhelming and make it look like you’re trying too hard. Your date might feel underdressed or even pressured by this look.
How to Dress for a First Date: Piece By Piece
Not all dates are the same. A date at a concert will look different from a date at a fancy restaurant. We’re going to list a few options for several situations, whether you’re going on a casual outing or you’re going all out.
Shirts
When it comes to shirts, the most important thing is that they’re well-fitting.
If you’re going to a restaurant that even might be fancy, consider a plain-colored button-up, or a white shirt under a blazer.
If you’re going to the park, something casual like a flannel or a polo (if you have a preppier style) is a great choice. Even a casual sweater for cooler weather can look very chic.
Dates at bars, arcades, or other more “recreational” spots can be dressed down. This is where band tees, tee-shirts, or streetwear are the most acceptable.
If your shirt is oversized, we suggest a french tuck. A full tuck is an older look and an untucked shirt is younger. Find what fits you.
Pants
For men, pants are pretty simple. Again, what’s most important is the fit. If your pants are baggy, make sure it’s intentional. Otherwise, a snug straight leg or bootcut style is best.
Khakis or black work pants are a great choice for a fancier first date. They’re neat, but understated.
For a casual date at the park, consider some well-fitting shorts. Denim isn’t the best choice for this, but a bright color or even khaki shorts can be a good match for an outdoor adventure.
For your ultra-casual dates at bars or coffee shops, well-fitting jeans make for a clean look that doesn’t ask for much attention. Dark wash over light wash, always.
Shoes
Shoes are one of the best places to show your style. They’re subtle (most of the time) and they’re close to the ground. If you want to get a little weird with it, pick your shoes.
Some nice boots, like Doc Martens, work well with any kind of date. They can be dressed up for the restaurant or down for the bar and they match almost anything.
While sandals for men used to be a no-no, they’re totally in style now. While they’re not recommended for your fancy dates, a casual sandal is perfect for a walk in the park.
Leather is going out of fashion as more people switch to a plant-based lifestyle. If you or your date is plant-based, consider the benefits of vegan shoes. Impress your date with your ethics and fashion all at once.
Accessories
This is another place that you can show your style.
If you’re someone with piercings or who loves jewelry, keep it simple but fancy. Yellow gold looks great on everyone, and it’s elegant and classy without being showy.
If you like hats, avoid brimmed ones unless this is an outdoor date. A casual beanie for a bar or coffee shop looks great and can hide a bad hair day.
A fancy date should be hat-free.
Skip the tie for the first date unless you’ve agreed to a more formal setting. While popular, they can make you look more uptight.
Show your personality in your accessories!
Are You First Date-Ready?
It’s normal to be nervous when you’re trying to figure out how to dress for a first date. The most important thing here is comfort. The more comfortable you are in your clothes, the more comfortable your date will be.
Pick something that you feel confident and attractive in, but keep your date’s style in mind as well. Now, head to your dresser and get ready to dress to impress a date.
