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7 Incredibly Stylish Valentine’s Day Outfits For Men

February 5th, 2024
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Valentine’s Day is right around the corner, and whether you’re planning a romantic dinner or something more casual, choosing the right outfit is of utmost importance.

Today, we’re showcasing seven versatile Valentine’s Day outfits for men, ranging from the edge of formal attire to dressed-up suited ensembles to casual looks with jeans and a blazer. All of these outfits are not only stylish but also comfortable and suitable for a variety of settings. So, get ready to impress your date with your impeccable style this Valentine’s Day and use this as a guide for inspiration no matter the occasion.

01

Classy Cocktail Attire

I’m not a grinch when it comes to dressing for a specific holiday, but I am not one to be super overt, literal, or necessarily guided by established norms of “what one should wear.” It’s in my personality to challenge expectations in that way and in my style to always err of the side of subtlety. When I see a room full of guys wearing something with bright red on Valentine’s Day, I can’t help but think, “That’s so obvious.”

If you’re of a similar mind — or just looking for a different approach — allow me to suggest the simple sophistication of a black turtleneck paired with black flannel trousers, black Oxfords, and a black and white houndstooth sport coat. It’s super chic and the patterned sport coat is a subtly playful substitute for an obvious pop of red.

02

“Formal” Burgundy Suit

This is perhaps the most straight up “festive” Valentine’s Day outfit of the bunch. A burgundy suit is a great choice for a more formal kind of date if you want to lean into the flavor of the Valentine’s Day color palette but want to keep it toned down just a bit. A burgundy suit isn’t flashy and never screams, “Look at me!” But it does always come off as extremely cool and confident — an equal parts cocktail of style mixed with suave, swagger, and sophistication. Styled simply with crisp white shirt, black grenadine tie, white pocket square, and black Oxfords, it’s a standout look that is sure to be memorable.

03

Suited Shades Of Valentine’s Day

Here’s a less formal approach to wearing a suit for your Valentine’s Day date but one that still gives a festive nod to the holiday. A dark brown Donegal tweed suit is a worthy alternative to the more classic navy blue or gray suit you may be tempted to reach for. It’s similarly versatile, yes, but is much more interesting when viewed up close — or even from afar, for that matter. Additionally, like navy blue and gray, brown is incredibly easy to pair with a variety of colors and looks exceptionally at home when styled with a pink shirt, burgundy tie and pocket square. It’s a uniquely festive look and one that is sure to stand out.

04

Classic Blazer With Jeans & Layered Sweater

When it comes to Valentine’s Day outfits for men, one of the biggest questions guys tend to ask is: Can I wear jeans on Valentine’s Day? The answer is most certainly, yes! There are all different approaches to Valentine’s Day date style and they all depend on the type of date you’re going to be going on. For more casual dates, putting together an outfit with jeans is a great idea.

However, since you will be going on a date, it’s important to dress up your jeans. The simplest way to do this is to begin with a pair of dark denim. Dark denim looks more “formal” and is therefore very easy to pair with a sport coat. Here, I’ve paired my jeans with a crisp white button-up shirt over which I layered a burgundy crew neck sweater. And then finishing the look off with a brown Glen plaid sport coat for a bit more polish.

05

Casual Blazer With Jeans & Layered Sweater

Because “can I wear jeans on Valentine’s Day” is such a hot topic and I firmly believe that you can, here’s another approach to the style. This outfit is even more casual than the previous one and features jeans in a slightly lighter shade of blue along with a classic Polo bear sweater for an added dose of fun and whimsy. The light blue OCBD coupled with a classic gray herringbone sport coat are easy ways to dress up the jeans while still maintaining an overall casual vibe.

06

Simple Sweater & Trousers

Sometimes simplicity is the order of the day and that was certainly the case when I put this outfit together. It really doesn’t get any easier than a turtleneck, trousers, and loafers. But here is where the details really matter and make a huge difference in terms of elevating the look. The turtleneck is chunky and cable knit, which makes it stand out. The trousers are made from a Donegal tweed, which also stands out. And the loafers are Alden’s Color 8, a very subtle burgundy for a very subtle festive feel.

07

Casual Cocktail Attire

Our last Valentine’s Day outfit is very similar to the first one in this post, but slightly more casual due to the gray herringbone tweed sport coat. What I particularly love about the foundation of a black cashmere turtleneck paired with black flannel trousers is that you basically have a blank slate from which to work with. From there, it really becomes a choose your own adventure in terms of what sport coat to wear and you can lean on your specific mood to make the final decision. Since I did choose a more “casual” sport coat, you’ll notice that I also opted for penny loafers instead of lace-ups to keep things more cohesive.

The Bottom Line

Choosing the right Valentine’s Day outfit comes down to the type of occasion you plan on making for yourself and your date. While we’ve covered a wide variety of approaches in this post — from very dressed up to more casual — there are certainly any number of alternatives. If you liked some of these looks but want to see even more HSS-approved outfit ideas, head on over to the Style Guide to get inspired and find your Valentine’s Day Style.

Thanks, as always, for reading and have a Happy Valentine’s Day!

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal, Today.com, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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Edited by Rachel Butler

Photography by Rob McIver

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Style February 2nd, 2024
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