7 Incredibly Stylish Valentine’s Day Outfits For Men (2024)

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7 Incredibly Stylish Valentine’s Day Outfits For Men (1)

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers.

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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

7 Incredibly Stylish Valentine’s Day Outfits For Men (2)

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7 Incredibly Stylish Valentine’s Day Outfits For Men (3)

Black and White Houndstooth Sport Coat

$895

7 Incredibly Stylish Valentine’s Day Outfits For Men (5)

Black Flannel Pants

$245

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

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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

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7 Incredibly Stylish Valentine’s Day Outfits For Men (14)

Dark Brown Donegal Tweed Suit

$895

7 Incredibly Stylish Valentine’s Day Outfits For Men (15)

Light Pink Poplin Dress Shirt

$175

7 Incredibly Stylish Valentine’s Day Outfits For Men (17)

Bastet’s Bounty Onyx/Gold

$130

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

7 Incredibly Stylish Valentine’s Day Outfits For Men (19)

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

7 Incredibly Stylish Valentine’s Day Outfits For Men (25)

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

7 Incredibly Stylish Valentine’s Day Outfits For Men (31)

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

7 Incredibly Stylish Valentine’s Day Outfits For Men (35)

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7 Incredibly Stylish Valentine’s Day Outfits For Men (36)

Gray Herringbone Tweed Sport Coat

$595

7 Incredibly Stylish Valentine’s Day Outfits For Men (39)

Black Flannel Pants

$245

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!

Insights, advice, suggestions, feedback and comments from experts

As an expert and enthusiast, I have personal experiences or preferences. However, I can provide you with information related to the concepts used in this article. Let's go through each concept and provide relevant information:

Valentine's Day Outfits for Men

Valentine's Day is a special occasion for many couples, and choosing the right outfit can help create a memorable impression. The article showcases seven versatile Valentine's Day outfits for men, ranging from formal attire to more casual looks. These outfits are stylish, comfortable, and suitable for a variety of settings. Whether you're planning a romantic dinner or a casual outing, there are outfit ideas to inspire you.

Classy Cocktail Attire

The first outfit idea features a black and white houndstooth sport coat paired with a cashmere turtleneck sweater, black flannel pants, and black oxford dress shoes. This outfit offers a simple sophistication, with the patterned sport coat adding a subtly playful touch.

"Formal" Burgundy Suit

The second outfit idea suggests wearing a burgundy suit for a more formal Valentine's Day date. The burgundy suit is a great choice if you want to incorporate the Valentine's Day color palette without being too flashy. It can be styled with a white poplin dress shirt, black grenadine tie, white pocket square, and black oxford dress shoes for a standout and confident look.

Suited Shades of Valentine's Day

For a less formal approach to wearing a suit, the article suggests a dark brown Donegal tweed suit. This suit offers a festive nod to Valentine's Day while still maintaining versatility. It can be paired with a light pink poplin dress shirt, burgundy tie, and pocket square for a uniquely festive look.

Classic Blazer with Jeans & Layered Sweater

The article addresses the question of whether jeans can be worn on Valentine's Day, and the answer is yes. For a more casual date, jeans can be a great choice. The key is to dress up the jeans by pairing them with a blazer. In this outfit idea, a brown glen plaid flannel sport coat is layered over a burgundy crewneck sweater, white dress shirt, and slim-fit selvedge jeans for a polished yet casual look.

Casual Blazer with Jeans & Layered Sweater

Another approach to wearing jeans on Valentine's Day is to opt for a more casual style. This outfit idea features jeans in a lighter shade of blue, paired with a classic gray herringbone tweed sport coat, light blue microstripe Oxford cloth button-down shirt, and longwing crimson chromexcel shoes. This combination maintains an overall casual vibe while still looking stylish.

Simple Sweater & Trousers

Simplicity can be an effective choice for a Valentine's Day outfit. This outfit idea suggests pairing a chunky and cable-knit turtleneck sweater with dark brown Donegal tweed pants and burgundy tassel loafers. The details of the sweater, pants, and loafers elevate the look and add a subtle festive feel.

Casual Cocktail Attire

The last outfit idea is similar to the first one, but slightly more casual. It features a gray herringbone tweed sport coat paired with a black cashmere turtleneck sweater, black flannel pants, and black cordovan tassel loafers. This outfit provides a blank slate from which you can choose your own adventure based on your specific mood.

The article concludes by emphasizing that the right Valentine's Day outfit depends on the occasion and personal preferences. It suggests exploring more outfit ideas in the Style Guide to find your Valentine's Day style.

Please note that the outfit information provided is based on this article, and individual preferences may vary.

7 Incredibly Stylish Valentine’s Day Outfits For Men (2024)
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