4 Valentine's Day Date Night Outfits for Guys (2024)

Last year, my fiancé and I’s Valentine’s date night consisted of dinner at our favorite restaurant…which we ate outside, in a rickety shack constructed on top of a New York City bus lane.

It was as romantic as you could get in the tail end of a pandemic, but I think my favorite part was the immediate change into sweatpants when we got home, and a Bravo marathon spent snuggling with our dogs.

Since it seems rickety shacks are here to stay in NYC, we’ll probably do the same thing again this year.

Whether you find yourself coupled up or single this year, leaving the house or binging reality tv at home, here are a few outfits to help you look and feel your best however you celebrate Valentine’s Day!

Check out 4 stylish men’s Valentine’s Day date outfits:

dressy night out
4 Valentine's Day Date Night Outfits for Guys (1)

suit: Bonobos | boots: Cole Haan

Where to wear it:

A romantic night out with your boo

Why it works:

Hopefully, you won’t fight me on suggesting you dress up in a suit for a special date night occasion.

Since this is a romantic evening out and not a business dinner, skip the dress shirt and opt for a long sleeve merino wool polo instead.

The overall effect? A chic, effortlessly cool vibe. Perfect for V-Day.

Add some Chelsea boots and you’re ready to go.

RELATED: 5 Outfits to Wear with Chelsea Boots

These boots from Mason are water resistant, perfect for when you find yourself in a romantic kiss on a slushy street after dessert.

Oh, and flowers (for her, obvs) always make a great accessory.

I’m very into hydrangeas right now…hint hint!

dinner at home
4 Valentine's Day Date Night Outfits for Guys (2)

camo pants: Everlane

Where to wear it:

Making dinner at home for your significant other

Let’s be honest, sometimes the best date nights are those spent at home. And when I’m not the one to cook?

That’s a literal ::chef’s kiss:: evening.

For a comfortable, yet stylish dinner-at-home look, go for a cozy sweater over a trend-forward t-shirt and comfy cargos.

Yes, cargos.

This pair, in a cool camo pattern elevate an outfit that would just as easily be paired with jeans.

Finish off the look with your favorite pair of low-top sneakers before sliding into house slippers later.

out with friends
4 Valentine's Day Date Night Outfits for Guys (3)

t-shirt: Fiorucci | shoes: G.H. Bass | jeans: Gap

Where to wear it:

A night out with friends

Why it works:

For a night out with friends, think Jacob Elordi off-duty vibes.

Start with a great pair of black jeans, straight or skinny fit (sorry not sorry, I just can’t get onboard with the relaxed fit that’s trendy again!).

Add a neutral-hued logo tee…my current favorite that i keep recommending to styling clients is from Fiorucci.

And of course, top it all off with one of Team SG’s favorite layering pieces for the season: the overshirt.

Overshirt, shirt jacket, shacket…whatever you want to call it…this thing looks f**king cool on every guy, including you!

There are endless options for this light layer.

You can go wild with a cool print or pattern, or keep your outerwear more subtle with a neutral option.

I like this one from Percival as it brings the whole look together and also adds some depth with the deep orange plaid.

Bring the look together with a pair of chunky boater-loafer mashups. These from Bass are a great option because they’re sturdy enough not to stick to the floor at whatever bar you end up at by the end of the night.

on the couch
4 Valentine's Day Date Night Outfits for Guys (4)

striped shirt: Todd Snyder (similar) | socks: Smartwool | shorts: Olivers

Where to wear it:

At home, specifically on the couch under a cozy blanket!

Why it works:

You’re cozy at home and not mad about it. When it comes to men’s Valentine’s Day date outfits, cozy loungewear ranks pretty high up on my list of recs.

So, throw on your sweats, grab a kombucha (anyone else letting Dry January ride?) and live your best life.

Maybe that means watching a movie you’ve been putting off because who can concentrate on a whole movie these days?

Or maybe it’s time to update that dating app profile and start swiping!

RELATED: How to Get More Dating App Matches

I know you’re at home and you feel like no one is going to see your fit, but what if you end up on a FaceTime date at the end of the night?! You just never know, so it’s worth putting a teeny bit of effort into your at-home look.

My current favorite hoodie is this peachy-hued style from Old Navy because it gives me hope that spring is coming.

I find myself in a groutfit (all grey outfit, natch) when lounging way too often, so I’m trying to branch out…for me and for my clients.

Complete the look by throwing on socks with your favorite pair of slippers. I recommend this Nike pair, which I recently bought for my fiancé.

He has not taken them off…partially because our dog thinks they are his toys, but I really think he loves them too.

Ready to go beyond men’s Valentine’s Day date night outfits?

Let Caroline shop for you!

Book a virtual styling session today.

4 Valentine's Day Date Night Outfits for Guys (2024)


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