#OOTD: How to Dress for Valentine’s Day This Year

So, Valentine’s Day is coming up. Whether you’re married or in a relationship (an old one or particularly, a new one!) or still looking for love, the question might be on your mind: “What the heck am I going to wear?” Based on your plans (Dinner? Drinks? Both!?), you might be faced with a dilemma. But I think the below #OOTD checks all the right boxes, no matter what. First up, stick with a classic winter blazer, and then layer up accordingly — in this case, that means a cozy, tailored flannel shirt from Faherty Brand, slim navy chinos and rugged leather boots¬†from my pals at Huckberry. It’s truly foolproof.

Granted, we’re not going full-on tuxedo here, nor are we recommending you wear one of the best flannel suits for a night out, but it’s still a sharp look that can work for a refined dinner-and-a-show outing, plus a nightcap. The key with dressing for Valentine’s Day comes in staying true to yourself — seriously. If you and your partner keep things low-key and make a nice dinner at home, leave the Grayers sportcoat behind. Heck, if you feel like wearing that same blazer out to a solo cocktail at your favorite bar, sure — go for it! The same building blocks are going to carry you through, from crucial outerwear like a¬†tailored topcoat¬†to accessories like a slim leather dress watch. We’ll top things off with a great Valentine’s Day gift, too. It’s all below, and I hope these picks lead to an enjoyable (if Hallmark-led) holiday — no matter what you do!

A crisp blazer, a sharp topcoat and stylish leather boots make for a winning Valentine’s Day #OOTD.

Even if this ensemble doesn’t quite line up with your Valentine’s Day plans, it’s hard to argue against the type of versatile building blocks it offers up — right? Starting with a¬†winter blazer from Grayers¬†gives you the flexibility to take your date (or heck, just yourself) out to drinks at a cool speakeasy or a refined sit-down dinner — or both. The¬†stylish flannel shirt¬†seen here is also made to be worn more casually — untucked at home, watching your favorite TV show — and it works in dressy situations, too. It could just be the best shirt for Valentine’s Day.

The same can be said for¬†slim navy chinos from Taylor Stitch, which work for a ‘staycation’ or a night at home. You’ll also stay weather-ready with the Rhodes Dean Boots, some of the best winter boots out there — it helps that they provide great traction and killer style. We’re keeping things on-point with a slim camel topcoat, and we’re further driving home that refined aesthetic with a¬†refined dress watch. Of course, it’s also of the utmost importance that you pick up a great gift for Valentine’s Day. And lest we forget … yes, you need good-looking underwear. Flint and Tinder can help.¬†Feel free to let me know your plans for Valentine’s Day on Twitter — to see how I’m spending mine (likely enjoying a delicious craft beer!), you can check out my Instagram.¬†

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Style Suggestion: What to Wear On Valentine’s Day

So, perhaps you think you’ve got everything sorted out for Valentine’s Day, from a killer dinner reservation — or a romantic night of your choosing — and a great gift. But not so fast there, fella. Have you given some thought as to what to wear on Valentine’s Day? The folks at Dappered always do a nice job tackling different scenarios, but today, we here at The Style Guide are helping you tackle the dressy dinner date (or night at the theater, or drinks and dessert … you get the picture). So, unlike our last style suggestion — that would be how to dress for winter travel — we’re going more refined and more tailored today. And crucially, we’re focused on layering up in style despite the chill. After all, Valentine’s Day is an excellent chance to show your significant other how much you care about them — and a small part of that is certainly putting your best foot forward. So, good luck out there and if you find yourself in need of more #menswear advice, don’t hesitate to hit me up on Facebook or Twitter. Or heck, Instagram. Go to it!


The Topcoat:¬† J. Crew Ludlow Topcoat in Italian Wool-Cashmere with Thinsulate — $470

As classic a topcoat as it gets, at a not-so-bad price.

As classic a topcoat as it gets, at a not-so-bad price.

First things first, let’s start with a stylish winter topcoat to fight the chill. J. Crew has taken its classic Ludlow suiting silhouette and translated that into a heck of a modern, functional topcoat. It’s going to be the perfect complement to a tailored winter ensemble , what with its crisp color and sharp silhouette. If you need to go with a cheaper option, you could always grab the ever-reliable JackThreads Tieman Topcoat.

The Suit: Taylor Stitch Telegraph Jacket¬†— $278 and Trousers in Grey Wool — $142.99

Quietly classic and essential for Valentine's Day.

Quietly classic and essential for Valentine’s Day.

Remember the handsome, essential Taylor Stitch Telegraph Jacket¬†from this site’s post on what to wear on New Year’s Eve? Or how to suit up this winter? If you jumped on it at the right time and find this suit currently sitting in your closet, good man. The rich wool, tailored fit and go-anywhere versatility mean it might just be your best suit — thus, it’s perfect for a night out. Of course, something as classic as the J. Crew Ludlow suit wouldn’t go amiss here, either.

The Shirt: J. Crew Ludlow Spread-Collar Shirt in Mountain Stream Stripe — $88

A sharp shirt in an unexpected color.

A sharp shirt in an unexpected color.

Although a classic white dress shirt or a baby¬†blue number would work just fine here, a striped¬† shirt with a strong collar is a unique and somewhat unexpected style move. The cool blue is a winter-friendly pop of brighter color, and given J. Crew’s quality, it’s the type of shirt that can be worn with other patterns — like a striped navy suit,¬†somewhat similar to The Man¬†Michael Fassbender.

The Accessories: Ties.com Hunter Green Antwerp Polka Dot Tie — $25¬†AND Ties.com Navy Edged Linen Pocket Square —¬†$10

Blue and green makes for a unique, eye-catching color combo.

Blue and green makes for a unique, eye-catching color combo.

First off, yes, we’re going with a linen pocket square in winter. In this instance, the navy detailing adds a nice contrast to the grey wool suit, and it offsets the lighter blue striped shirt. Similarly, a green tie offers a bit of rich contrast to the suit-and-shirt combo. Plus, the polka dots add some nice visual interest, and it’s really tough to beat the standout prices on both of these pieces. Ya feel me?

The Boots: Thursday Boots Honey Suede Duke Boot —¬†$199

A unique alternative to your typical dress shoe.

A unique alternative to your typical dress shoe.

Boots are indeed the move in this case, and particularly in suede — the texture just looks right up against grey wool, and this Honey shade is particularly handsome. While you could stick with a pair of classic men’s dress shoes, these boots are going to help you navigate slippery terrain with fashion and function in mind. If it gets too snowy outside, you might want to consider the waterproof Thursday Boots Cognac Suede Wingtip Boot.

The Belt: J. Crew Textured Leather Dress Belt — $68

Go with a reliable belt from a reputable brand.

Go with a reliable belt from a reputable brand.

If you’re going with a classic, essential J. Crew topcoat (and potentially a suit, too), why not pick up a¬†stylish, simple and effective dress belt from said brand? The price is a bit, well pricey, yet this is the type of dress belt you’ll be able to wear frequently — even with dark denim and¬† a V-neck sweater. Easy enough, right?

The Watch: Orient Ray II — $234.50

The toughest watch in your collection? Maybe. The right Valentine's Day pick in terms of style? Without a doubt.

The toughest watch in your collection? Maybe. The right Valentine’s Day pick in terms of style? Without a doubt.

You surely didn’t think we’d leave anything to chance on a day like Valentine’s Day, right? No, not even a watch like the Orient Ray II is out of the question on this night. It’s an utterly classic, sharp and stylish watch made for all kinds of tailored occasions — especially a beautiful evening on the town. The stainless steel diver has connotations both dressy and rugged — maybe that’s why it’s a favorite of James Bond — and this timepiece is no different. Yes, the Orient Ray II¬†is a tough watch for the rest of the year, and it’s a handsome complement to the hues of blue and green in the rest of this ensemble.

The Socks — American Trench Pima Cotton Houndstooth Socks — $16.98

An easy pick when it comes to stylish socks that complement an outfit.

An easy pick when it comes to stylish socks that complement an outfit.

If you don’t recognize American Trench by now, then you’ve got another thing coming … just kidding. When a brand makes versatile, crisp socks that fit well and feel great, you should buy ’em in bunches. And when it comes time to wear them on special occasions, you should certainly break them out. These Pima Cotton Houndstooth Socks are essential, versatile and add just enough color and texture to this outfit.

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Alright, did that post help you take care of your shopping? At least a little bit? It’s crucial to work with what you’ve got in your wardrobe — say, the essential Taylor Stitch Telegraph Jacket¬†— and make it work for you in multiple situations. When¬† matched up with a unique striped dress shirt and smart accessories in eye-catching hues, it’s hard to go wrong. Plus, sharp suede Chelsea boots add a bit of visual intrigue, while a tough-yet-refined dive watch like the Orient Ray II¬† is the way to go in this instance. Hopefully, this is an outfit that impresses your significant other — just don’t forget about a meaningful gift and a fun evening. Deal? Deal. High-five, y’all!

Thanks for reading and stay stylish,

-Beau