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.

NOV CAMPAIGN: Horizontal banner with shoes and logo (border)

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

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