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What to Wear on a Valentine's Day Date - Men's Date Outfits

We blinked and suddenly Valentine’s Day is around the corner, and that means that it’s time to start thinking about Valentine’s Day attire. Here’s the truth of the matter, guys: looking good on V-Day isn’t just something the ladies have to worry about. You’ve to be thinking about your Valentine’s Day date outfits, too! 

What should guys wear on Valentine’s Day?

It all comes down to classy Valentine’s Day outfits. But what’s classy to you might not be classy to the next guy, or to your special lady, for that matter. That’s why we’ve put together this go-to guide. 

In this article, you’ll find ideas for men’s date outfits that are not only great for Valentine’s Day, but great for dates in general. Keep in mind that these are choices meant for a colder season, and they probably won’t fare well for dates in the summer

Are you supposed to wear red on Valentine’s Day?

You’re probably aware of the fact that red is a festive Valentine’s Day color. But just because red is the color of love doesn’t mean that your Valentine's Day attire has to consist of it. If you want to sport it, we suggest using it as an accent instead of going all out. 

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Outfit Idea #1: Day and Night

The first of our Valentine’s Day outfit ideas was chosen for its versatility. You can go from day to night with this great ensemble, from strolling around the city to settling down at dinner to exchange gifts.

What is the best outfit to wear on Valentine’s Day?

At Perk, we say that the best Valentine’s Day date outfits consist of something that makes you feel comfortable. That doesn’t mean sweatpants, but Valentine’s Day isn’t the time to try out brand new styles. You want to feel confident and authentic!

This men’s Valentine’s Day date outfit is sensible and great for winter. It’s simple and casual but with a classy edge, making it just right for a V-Day dinner with your girl. Here’s what you need to pull it off:

  • A black ribbed turtleneck
  • A navy blue overcoat
  • Chelsea boots
  • Chinos of your preferred color (but we prefer black or burgundy) 

This Valentine’s Day attire is comfortable, stylish, and will surely make you feel confident. 

Outfit Idea #2: Casual and Formal

This outfit shines the spotlight on the ever-so-versatile turtleneck. This type of sweater can be dressed up or dressed down - but, no matter how you wear it,  you’ll look chic. 

What are the three colors of Valentine’s Day?

As for Valentine’s Day decor, the three colors are most definitely red, white, and pink. But when you’re dressing yourself in classy Valentine’s Day outfits, you might not want to combine them in fear of looking like a candy heart. Instead, stick to subtle callouts like a pink tie or a red scarf.


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If you’re not into ties, the turtleneck (or roll-neck) sweater is a great alternative. Here’s how to pull it off on V-Day:

  • A navy turtleneck sweater
  • Brogue oxfords
  • Chino pants
  • A suit jacket or a denim jacket, depending on the formality of the occasion 

Outfit Idea #3: Black as Night

There’s no color classier than black, and this Valentine’s date outfit is a great way to prove that. 

What colors do men wear on Valentine’s Day?

Men can wear any color they want on this holiday of love, but we find that the best include black, deep red, and navy blue. You don’t want to outshine your date with loud and brash colors, so keep your palette subtle and simple. 

Wearing all black is a great choice for Valentine's because you’re sure to look sophisticated, mysterious, and sleek. Everything in the outfit should be black, but here are some details to use to create visual interest: 

  • Red lapel flower
  • Red and white checked pocket square
  • Charcoal gray blazer 

Outfit Idea #4: Sporting the Tie

If you’re ready to hang up your t-shirt and get fancy for the night, sport a necktie, button-down, and waistcoat. 

What is the best color to wear on Valentine’s Day?

Here at Perk, we believe that confidence is the key to looking good in anything. So, if you feel the best in black, wear black on Valentine’s Day. If you feel great in red, wear red! 

For this ultra classy look, you’ll need a few key items. They include:

  • Dress pants
  • Oxford cloth button-down
  • A silk neck tie (perhaps in red or pink)
  • A textured vest 
  • Brogue dress boots
  • Woolen pea coat
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Staying Classy on V-Day

We want you to enjoy Valentine’s Day with your special date, and you can make the most of the night when you feel great in your Valentine’s Day date outfit. For more inspiration on how to style your outfits for a date, check out Perk’s blog