24 Valentine’s Day Outfits for Men: What to Wear for Every Date

24 Valentine’s Day Outfits for Men: What to Wear for Every Date

February 14th is around the corner and it’s coming up fast. Make sure you’ve got flowers, chocolates, and a killer outfit. But don’t worry if you haven’t got the perfect digs picked out just yet. We’ve tons of ideas for when it comes to Valentine’s Day outfits for men, check them out.


What to Wear on Valentine’s Day

Alright, guys — it’s Valentine’s Day and it’s your time to shine. Whether you’re taking a partner out, you’re going on a first date, or just hanging with friends, it’s important you look fresh. That’s why we’ve put together the ultimate guide to V-Day outfit ideas. Plus, we break them down into what kind of date you’re going on, let’s go!


Fancy Dinner

Layers on layers on layers

Grab a scarf, a vest, and an overcoat for the ultimate fancy dinner entrance. Don’t be afraid to accessorize with this one!


Put on your V-Day vest

All you need to nail this one is a pressed white shirt, and a matching vest and jeans. Pop on a pair of smart glasses and that’s it!



Khaki’s where it’s at

Don’t be afraid of the khakis, embrace them. And pair them with some dark shoes, a dark sport coat, and a lighter button-down.


Show off those ankles

Nothing says “dining with confidence” quite like some bare ankles. Go for a fitted suit with a pair of loafers, and ditch the socks.


Casual Dinner

Camel is in

Say it with us. Camel. Is. In. This includes blazers, overcoats, turtlenecks, you name it. Plus, you can pair it with white or light-colored denim.


It’s all in the tee

Yes, you can 100% wear a t-shirt to a casual Valentine’s Day dinner. But the key is, it has to be of high quality. Pro tip: you can find some quality, fitted t-shirts right here at True Classic.


For cold weather…

If you’re going out for a casual dinner somewhere cold, go with a puffy jacket and matching monotone palette.


For warm weather…

In warmer spots, reach for distressed jeans and a nice linen button-down shirt to stay cool. Don’t forget your shades!


Movie Date

The classic baseball tee

Movie theaters get chilly, dudes. This Valentine’s Day, go with a tailored denim pant, some fresh white sneakers, and a classic baseball tee to stay comfortable.


Puffy vest and patches


This one is for all the edgy, artsy guys out there. Cozy up to that special someone with some distressed, patched-up denim and a puffy vest.



The rom-com outfit

If you and your partner are heading out to watch a romantic flick, why not dress the part? Think about your layers!


Be the bad boy

Get even edgier this Valentine’s Day with some dark jeans and a tough leather jacket. The key here is making sure you’ve got the perfect tee underneath.


Happy Hour

Play it cool

Happy hour is all about having fun. Pop on your coolest outfit (we suggest a denim jacket, at least) so you can relax and let loose.


Hoodies and jackets = perfect

V-Day happy hours are the perfect place to show off your wardrobe. Sport some layers with a hoodie and a jacket to kill two birds with one stone.


Sneaks and a long-sleeve tee

Ahhhh, the classic long-sleeve tee. Pair it with some light-colored jeans, some dark sneakers, and a high-quality tee underneath.


Cool cut-offs

Hang out with all your favorite friends this Valentine’s Day while you rock your favorite pair of denim cut-off shorts.


Group Date

Double up on denim

Going on a double date? Why not sport the double denim, too? It’s a classic look that never goes out of style.


Embrace the color pink

Show your Valentine’s Day pride this year by wearing a comfortable pink sweatshirt. It’s a surefire way to signal your holiday spirit!


Layer it up

Group dates usually mean a few location changes, maybe from dinner to the movies. So wear smart layers to keep up with the group’s pace.


Roll your cuffs

Show off your ankles, rock the double denim, and don’t be afraid to roll those cuffs. It’s cool, it’s comfortable, and it’s fresh.


Theater Show

Matching shoes and jacket

Get classy by matching your favorite jacket with the same color in shoes. It’s literally the easiest way to get a winning theater outfit combo.



A monotone look is ideal for a theater V-Day date. It’s a classy look plus, you’ll have an overcoat to give your date in case they get cold.


Pressed and pleated

Heading to the theater straight from work? That’s easy — just sport your usual work outfit, but pop a matching tie and blazer on top.



Put a lid on it

Never be afraid to rock a hat or any other accessories. The theater is a place of expression. So why not celebrate this Valentine’s Day in style?


Now your toolkit is filled to the brim with flawless Valentine’s Day outfit ideas for guys. And remember, when in doubt, just go with some dark denim and a fresh tee that fits like a dream, then dress your outfit up or down to match the setting.

Get even more fashion tips for guys and check out the rest of our blog. It’s got tons of cool ideas, fun reads, and ultimate guides just like this one.

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