Valentine’s Day Date Outfits for Men: A Winter Lookbook3 min read

What’s up fellas. With V-Day on the horizon, I put together this article and little lookbook featuring 4 Valentine’s Day outfits to help inspire you on this holiday of love. 

Valentine's Day Outfits For Men & Date Night Outfit Ideas | GENTLEMAN WITHIN

These looks also double as great winter date night outfit ideas.

Let’s get started.


To watch the lookbook, be sure to check out the video below.

DATE NIGHT OUTFIT IDEAS For Men | Valentine's Day Winter Style Lookbook

OUTFIT 1: From Day to Night

A casual day-to-night Valentine’s Day outfit.

Valentine's Day Look 1: Rolled & Red 1 | GENTLEMAN WITHIN
Texting bae.
Valentine's Day Look 1: Rolled & Red 2 | GENTLEMAN WITHIN
OUTFIT DETAILS—Car Coat: Tailor Store | Turtleneck: Amazon | Boots: Thursday Boots Co. | Chinos: Bonobos | Driving Gloves: Elma

This first Valentine’s Day inspired outfit is a fairly sensible winter look. It’s simple, casual and yet still refined, which makes it a perfect outfit for a Valentine’s Day date.

I went with a black ribbed turtleneck sweater under a navy car coat, and bold burgundy chinos to inject a bit of richness into the fit. And down low I threw on the comfortable and stylish suede chelsea boots.

Overall, this is a look that can take you from a chill day date to a night on the town or a relaxing evening back home. You’ll be casually cool, comfortable and stylish.

6 Dating Tips to Make the Most of Cuffing Season (And Get the Girl) | GENTLEMAN WITHINRelated: Check out this guide — Dating Tips for Men to make the most of cuffing season.

OUTFIT 2: A Casually Formal Affair

Dress up or dress down the elegant turtleneck sweater.

Valentine's Day Look 2: Formal | GENTLEMAN WITHIN
What’s up boss.
Valentine's Day Look 2: Casual | GENTLEMAN WITHIN
OUTFIT DETAILS—Denim Jacket: Everlane | Turtleneck Sweater: Banana Republic | Tailored Trousers: Bonobos | Shoes: Allen Edmonds | Socks: Boardroom Socks | Watch: Daniel Wellington | Lapel Pin:

The turtleneck or rollneck makes for a great necktie alternative.

For this look I paired a lightweight navy, turtleneck sweater with a blue shark skin suit. This dresses down the suit just a little bit while remaining classy.

Alternatively, I dressed down the suit even further by swapping the suit jacket for a mid-wash denim jacket. This gives the look more of an edge, while still remaining elevated.

As for the shoes I went for a pair of essential half brogue oxfords in a walnut shade. Make your Valentine’s Day great again with this stylish getup.

OUTFIT 3: The Blackout

A classy Valentine’s night.

Valentine's Day Look 3: BLackout 1 | GENTLEMAN WITHIN
OUTFIT DETAILS—Suit Jacket: Spier & Mackay | Dress Shirt: Amazon Essentials | Pants: Uniqlo | Shoes: Beckett Simonon | Socks: Boardroom Socks | Lapel Flower: The Dark Knot
Valentine's Day Look 3: BLackout 2 | GENTLEMAN WITHIN
Kick game, 100.

I’m calling this outfit The Blackout since it’s an all black look which makes it perfect for Valentine’s date night. It’s a bit mysterious while turning up the sleek and stylish dials.

Everything is black with exception to the blazer which is more of a charcoal gray in a silk woolen material. And for the small details I have a red lapel flower paired with a white and red check pocket square.

Rock this all black look and you’ll be looking, smooth, suave and sophisticated for your special lady.

10 Prove Techniques For Approaching And Meeting Women | GENTLEMAN WITHINRelated: Check this guide — 10 proven techniques on How to Approach Women.

OUTFIT 4: All Tied Up

Classy it up a bit with a necktie, button-down and waistcoat combo.

Valentine's Day Look 4: All Tied Up 1 | GENTLEMAN WITHIN
SHOP THIS LOOK—Pea Coat: Spier & Mackay | Shirt: Spier & Mackay | Tailored Trousers: Bonobos | Boots: Allen Edmonds (Similar: Idrese Micah) | Necktie: Amazon
Valentine's Day Look 4: All Tied Up 2 | GENTLEMAN WITHIN
Oh hey, cutie.

The final look I decided to keep things refined with dress pants, oxford cloth button down, a pink silk neck tie and a textured vest.

For the top layer I opted for an olive green woolen pea coat as it’s a stylish option, but still keeps me warm. And finally down low I went for the chocolate brown full, brogue dress boots. It’s the Dalton from Allen Edmonds, one of my favorite boots for dressier outfits.

You’ll get style points and bedroom points for this one as what woman doesn’t like her man tied up?


Alright gents, there you have it! 4 different Valentine’s Day outfits for men that I hope can inspire your Valentine’s Day getups or date night outfits this year.

Originally published on Feb 11, 2018. Since updated for accuracy and comprehensiveness.

Valentine's Day Outfits For Men & Date Night Outfit Ideas | GENTLEMAN WITHIN

Which of these Valentine’s Day outfits is your favorite?

Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.

Cheers to your style!



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  1. John Calvin says

    Do you have a pic of the final outfit – what you were wearing underneath? thx

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