Share
- Share on Facebook
- Tweet
- Share to Flipboard
- Pin it
- Post to Tumblr
- Submit to Reddit
- Share on LinkedIn
- Share on WhatsApp
- Email
All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
When picking a men’s first date outfit, you’re going to want to put your best foot forward because dressing to impress is a great way to show them you care. If you’ve already decided on the location and mentally prepped yourself, next up is the ‘fit. What exactly should you wear on a first date? Well, it’s up to your personal style, the date location, and the date activity.
Depending on what you have scheduled, there are a slew of options when it comes to your outfit choice. Going on a scenic hike? Opt for a cool hiking sneaker. Taking them out to a fancy dinner? Then you’ll need a nice dress shirt that’s a mix of luxe and casual. Here at StyleCaster, we’ve gone on a quite few first dates ourselves. You could say we’re masters of nailing the outfit, so we’ve put together a list of incredible options that’ll work for a range of destinations and activities. But just remember to go with what you feel comfortable and confident in, and be sure to also incorporate your personal style so your date gets to know a bit about you through your sense of fashion.
Don’t sweat this big decision too much, though. We’ve got you covered with clothing that’s guaranteed to impress your date and keep you feeling super confident while you get your rizz on. From a pair of classic sneakers to an edgier mesh top, our picks truly cover all of the bases. Keep reading to see some of our favorite men’s outfits for a first date.
Dinner
BOSS Hank Kent Slim Fit Dress Shirt
$89.60$12830% Off
Buy Now
The romantic dinner date is definitely the type of first date that you’ll want to get a little fancy for, but you don’t have to slip into a full-on suit (unless you want to, we’re here for it). This dress shirt from BOSS is giving gentleman who really put in the effort in your dream romantic comedy — trust us, they’ll like it.
Park
Adidas Samba OG Shoes
ADIDAS $100
SSENSE $200
Want to keep it casual but show off a bit of style? The Adidas Samba has been trending for some time and we honestly think it’s here to stay — it’s safe to safe we think it’ll be in your closet for years to come. This laidback sneaker would look incredible with a pair of trousers or shorts.
Drinks
FRAME L’Homme Slim Jean
$210
Buy Now
Meeting at the bar can be the perfect place for a first date — you’re not completely alone so it’s not too awkward and it’s not dinner so you’re not trapped if it doesn’t go well. Opt for this slim-fit denim from FRAME, a gorgeous medium blue wash that can be dressed up or down.
Coffee
The North Face Beige Versa Nuptse Down Jacket
$370
Buy Now
As the weather gets a little colder, you’ll want to ensure you have a puffer coat to keep you warm. If you’re keeping it casual with a coffee date, impress your date with a cool velour take on this The North Face staple. The orange-brown shade works well for autumn — bonus points for it matching your latte.
Exercise
On Lightweight Color Blocked Quick Dry 7″ Shorts
$79.99
Buy Now
Need a first date activity that’s not your average? Go hit a workout class together or meet for a quick run. Depending on how intense it gets, these breathable shorts are bound to keep you feeling good and dry whether you’re boxing or hitting pilates. Did we mention there’s a back pocket where you can store your wallet and phone? Absolutely genius.
Concert
AllSaints Tona Slim Fit Leather Jacket
$659
Buy Now
You’ve bonded over an artist you both really like and they’re in town, so naturally you’re going for the concert date. Coming into these colder months, a thinner leather jacket like this one from All Saints will work for any music outing, whether you’re sitting down in a box at the opera or jumping around to your favorite indie band. Wear it with a fun dress shirt or fuzzy sweater underneath to really add to the fit.
Thrifting
Courrèges Bumpy Contrast Mesh Tank Top
$300
Buy Now
Hypebeast said it themselves, the mesh shirt is here to stay. If a man wore this to our first date, we’d put a ring on it. Obviously this is not a tame choice, but if you’re a bit of a fashionista, wear this stylish mesh top on a thrifting date where you’ll be having a blast shopping and getting to know each other’s unique flairs.
Hiking
Merrell Nova 2 Sneakers
$140.95+
Buy Now
If you’re going on a fun hiking date, you definitely want to opt for comfort and coolness and Merrell is definitely a brand that embodies both. If you decide you want to traverse another trail and stay a bit longer (maybe you’ve really hit it off), you’ll both look good and feel good in these sneakers.
