Date Night Outfits For Men: What To Wear On Valentine’s Day

by Chris Xavier  |  in Style Tips

V Day can be a tricky one to navigate and there’s a lot to plan. Do you really need the predicament of what to wear adding to your stress? (Of course not.) We’re here to give you a few solid date night outfits so you don’t have to worry about what to wear on Valentine’s Day.

While we do our best to give our partner the ideal romantic experience on Valentine’s Day—or ourselves if we’re single and want to indulge in a little treat—there are so many variables at play.

Damn, what are my girlfriend’s favorite chocolates again? Do they like roses or petunias? Is jewelry too serious if we’ve only been dating for three months? She said she loves Italian food, but every Italian restaurant in the city is booked until 10 PM and I have work in the morning!

date night outfit ideas - keep it classy for wine and dinner like this black sweater
Photo by cottonbro studio

The one constant that we can control is how we present ourselves. Good grooming and a strong outfit will give your partner a great impression of you on the most romantic day of the year.

Luckily, I’m here to help you pick out a winning outfit no matter what kind of date you plan for the big weekend.

Check out each of the scenarios below!

What To Wear To Dinner and Drinks

I’m a sucker for the classics, and it doesn’t get any more classic than a dinner and drinks date with a special someone on Valentine’s Day.

Everyone does it for a reason: the candle-lit ambiance, cozy atmosphere, light piano jazz playing over the Sonos speakers carefully hidden throughout the restaurant.

It’s hard to beat enjoying a great meal with a date, whether you’ve been together for a decade or if this is the first time you’ve met IRL.

COS cotton twill chinos, BR long sleeve cashmere polo shirt, Barbour waxed jacket, Paraboot derbies

Though unconventional, I like to start crafting an outfit with pants. For a dinner date at a nice restaurant, the darker the pants the better.

You can go with a pair of dark blue selvedge denim. And, to the surprise of no one, Levi’s has a great offering for under $100. If you don’t feel like doing jeans, a pair of straight or relaxed-fit trousers will do the trick.

COS has been making a lot of great pants lately. Their cotton twill chinos have just the right amount of elevation and pizzazz.

A collared cashmere sweater would be a style swerve in a world full of oxford collar button-downs and pique polo shirts (no disrespect to those legends).

You could elect to stay with a black one to keep a monochromatic look or you can get a little creative and choose another colorway. Personally, I love a navy and black color combination as I think it’s equal parts subtle and tasteful.

This navy cashmere long-sleeve polo shirt from Banana Republic is gorgeous and will serve you many, many years after Valentine’s Day Dinner.

On the feet, black leather shoes reign supreme in this kind of environment. While loafers are certainly trending, I think a derby would be the best choice. The two best options are Paraboots and Doc Martens.

Versatile, stylish, and timelessly cool, these shoes will round out your outfit nicely.

Throw on a Barbour jacket, a leather blouson, or a suede trucker up top, maybe a chain or two, and either a stainless steel or leather band watch and you’re going to be the best-dressed man at the steakhouse. Just don’t forget to tip the wait staff well.

What To Wear On A Picnic Date or A Hike

Maybe you live in an area rich in public parks or hiking trails. There’s nothing like the great outdoors, especially with the promise of pretty views, fresh air, and good company.

Bring a picnic basket with your favorite sandwiches, some crackers and cheese, grapes, and a bottle of wine to make for a great afternoon.

Gramicci pants, A&F vintage-inspired tee, North Face Retro Nuptse puffer, Adidas Stan Smith

Depending on the weather, you have a lot of options for this occasion. Luckily, Gorp-core is one of the predominant trends of the moment, so there’s no shortage of inspo for outdoor dressing. 

I’m from San Francisco, where it is perpetually a cool 55 degrees, but the cool weather doesn’t stop us from taking part in all kinds of outdoor activities.

A pair of Gramicci pants would be your best bet as they are affordable, durable, and come with an elastic waist (so you can stretch out a bit after your hearty lunch).

I’d opt for a cool graphic tee on top to show off a little personality. There’s nothing cooler than a good vintage (or vintage-inspired) T-shirt, and you probably already have several laying around.

Top it off with a puffer jacket—Patagonia, The North Face, Columbia, And Wander, and Gramicci all have great options.

If you want to go a bit more eclectic, check out the Japanese brand South2 West8. They’ve collaborated with Supreme in the past and have a big presence across the Pacific Ocean. Their patterned jackets will give you the pop you want.

On the feet, go simple. Beat-up Air Force 1’s or Stan Smiths will forever be cool. On the noggin, a beanie is best in case the temperature drops. You can always take it off if it rises.

What To Wear To The Beach, The Pool, Or Any Place With Water

Can you name something more relaxing than sitting poolside at a resort, piña coladas arriving at your bungalow while French house music plays in the background? Didn’t think so.

If you’re looking to get away this Valentine’s Day and a warm, watery destination is in your itinerary, you’ll need to come prepared with the proper attire.

Nike trunks, Todd Snyder button polo, Fear of God mules

Pool dressing isn’t inherently difficult, but there are a lot of bad swimsuits out there to choose from, so it can be easy to fall into a trap.

First of all, you’re gonna need to throw on a full outfit on the way to the pool, not just your swim shorts. And please, for the love of God, do not wear thong flip-flops. You want to go with some clogs or respectable pool slides.

I’ve really been into the Fear of God California Loafer, which comes in at about $200 and is one of the sleeker clogs on the market. If you’d rather go the slide route, you don’t need to blow a bag on the Gucci or Moncler versions — stick with the basics from Nike or Adidas.

Up top, you need short sleeves. You may not get in the water at all, so you want a stylish shirt that you’ll feel great in all day. I’d throw a curveball here and wear a knitted polo for a touch of elegance.

My favorite is this subtle yet elegant piece from Todd Snyder. Check out Abercrombie for more affordable alternatives. They have at least a dozen knit polos on their site right now.

The most important part is your swimsuit. The Nike Volley Short are the best trunks that you can buy for under $50–they’re perfect. You can choose between a 5″ or 7″ inseam and every color on the rainbow.

They’re understated and super comfortable. You’ll buy a pair and immediately buy another in a different color. They’re that good.

What To Wear On A Fancy Night Out (Theatre, Opera, Symphony)

Perhaps your partner has an affinity for the theatre or the opera. Maybe you scored tickets to the symphony. 

There will surely be a dinner and drinks component to the night before or after (most likely before) the show and a nightcap at the bar around the corner. Regardless, you’re going to want to show out for this.

Bright navy suit and striped dress shirt from SuitSupply, Drake’s x Aimé Leon Dore tie, Cole Haan oxfords

A suit is the most appropriate option here if you’re having a full night on the town. I’ve been really into suiting lately. I threw on a suit for New Year’s Eve dinner and felt great all night.

Your suit doesn’t need to break the bank (but if you have an expensive suit, this would be the time to bust it out). You can wear an affordable from suit from Uniqlo and still look great, especially if it’s been tailored to fit your body properly.

I’d go for a navy blue, charcoal grey, or brown—avoid black because you don’t want to be confused for someone on the staff. A white or powder blue shirt is always a good move, but striped shirts work great as well.

The Perennial Suit from Suitsupply

The perfect suit to have, if you only have one suit. Available in classic colors and a variety of cuts.

Shop SuitSupply

I bought a couple striped poplin shirts from J.Crew that I can dress up or down.

A tie is optional—we, as a culture, seem to have moved past them—but I say, go with a tie. And when you do, try and go vintage. I’m in the market for a vintage one from Hermes.

A lot of the prints border on novelty, but that’s the fun in wearing a tie when you don’t have to. From eBay to the RealReal to Grailed to Etsy, there are vintage tie options everywhere!

On the feet go for tan oxfords. They go great with any of the suit colors mentioned above and will age very nicely. Look no further than Cole Haan. It’s the best value for money and will definitely hold up over time.

To switch things up, you can do a classic pair of Wallabees, but only if you’re brave.

Now you’re ready to go enjoy Carmen… or Figaro… whatever it’s called. You get the picture.

Staying At Home? Outfit Ideas For A Cozy Night In

Ah, my favorite! For a lot of us, the ideal Valentine’s Day date is the one at home with our partner. Whether or not you decide to cook or order takeout from your favorite Indian restaurant, spending a night in with your partner can be the best date of all.

Todd Snyder x Champion sweatsuit, A&F vintage-inspired tee, Fear of God mules

You and your partner can agree to dress down, calling for the most casual outfit of the bunch. With that said, there’s a way to go low-key without sacrificing style. 

There’s nothing that looks and feels more lux than a matching sweatsuit in either grey or cream. The ongoing Todd Snyder x Champion collaboration is a perfect high-end sweatsuit for under $300.

Aimé Leon Dore also has a great option at a bit higher price point, while Gap has the best budget alternative. Whatever you spend, you’ll look put together and comfortable simultaneously.

So get comfortable, cook your pasta, or order your tikka masala and turn on the latest A24 film!

At The End of the Day, Don’t Stress Too Much

Dressing for Valentine’s Day shouldn’t be your main priority. You have bigger fish to fry! Your focus should be to share love with your partner, be that with the perfect plans or the perfect gifts. Everything after that is a bonus. 

Your outfit should be simple with elevated takes on classic silhouettes to show your partner that you want to put your best foot forward for them on this most romantic day. Just remember to relax.  Good vibrations, my man!

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