men’s valentine’s day style

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.

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.

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.

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.

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.

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.

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.

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.

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.

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

Editor’s note: For a bevy of style suggestions covering how to suit or dress down, click here.

So just as we talked about in last week’s Valentine’s Day gift guide post, the big is almost here — and our Style Suggestion series is back! Now, Valentine’s Day falls on a Sunday this year, so perhaps that makes things a bit different for you — maybe you’ll be away and traveling for the weekend perhaps? Or staying at home to catch a sharp Sunday dinner? At any rate, it’s a day where you’ll want to look your best for your significant other. Even if you go the less formal route, it’s worth it to still look into some style upgrades — like throwing on a slim pair of denim or even just an crisp pair of leather sneakers. The below Style Suggestion however, like last year’s Valentine’s Day Style Suggestion, goes the more formal route — it’s a classic look (hopefully) with some modern touches. Read on, suit up and let me know how you’re dressing for the day or the weekend!

The Suit: Combatant Gentleman Charcoal Slim Fit Herringbone Suit — $200

A reliably classic color and cold-weather fabric make this suit a winner.

It seems that in tailored situations here at the ol’ Style Guide, Combatant Gentleman has been the suiting pick of choice, from New Year’s Eve to holiday parties and beyond. And for good reason, too — there’s hardly a better suiting deal out there that brings solid quality, a reliable fit and a plethora of suiting options to chose from. This Charcoal Slim Fit Herringbone Suit is a solid pick in this case, however, because it’s versatile, sharp color that can work in plenty of other situations besides Valentine’s Day — a great budget pick-up. The Italian wool herringbone weave is a seasonally appropriate touch in this cold weather, too (if it’s warm where you are, you could always rock a chino suit). Don’t forget that overcoat, either.

The Shirt: J. Crew Factory Voyager Dress Shirt in End-on-End — $41.50

Another well-priced staple from J. Crew Factory at a great price.

Just as with Combatant Gentleman, it’s tough to find a better deal for the quality than J. Crew Factory (although the folks at Combat Gent do a nice job with shirting, too). But if you’ve been looking to check out the Factory line and haven’t gotten to it, here’s your chance. This end-on-end shirt mixes in some subtle texture, a slim fit and a great price. The wrinkle-free aspect is another nice touch that should make it easier for travel, too. And the light blue is going to stand out nicely under the darker charcoal suit — it’s another piece that can work in many other situations outside of this one. On another note, if you should find yourself in need of a great undershirt to keep you cool throughout the night, head to Tommy John.

The Tie: The Tie Bar Midnight Navy Grenafaux Tie — $19

Does this tie look familiar? If you read this blog regularly, it should!

If you happened to catch this blog’s holiday party Style Suggestion, perhaps you recognize this tie. The Tie Bar’s Midnight Navy Grenafaux Tie is quickly becoming a Style Guide favorite — it’s not often you talk about a tie being reliable (trust me), but this number is crisp, visually interesting and a solid contrast to the lighter blue shirt. It being Valentine’s Day and all, it’s never a bad thing to draw some color palette inspiration from James Bond, either. The price is remarkably solid, and you could wear this tie with a crisp white dress shirt in place of the J. Crew Factory end-on-end shirt if you wanted.

The Pocket Square: The Tie Bar Owen Plaid Pocket Square — $10

A unique pattern and color scheme help this pocket square stand out nicely.

When on the hunt for great accessories in a pinch, it pays off to turn to a trusted retailer time and again — in this case, our friends at The Tie Bar. This Owen Plaid Pocket Square is an excellent bit of contrast to the dark charcoal suit and multiple shades of blue in the top half of this ensemble; the rich burgundy is also a change of pace from more standard pocket squares (although a classic white pocket square could work here, too).

The Shoes: Jack Erwin Adam Wingtip Oxford — $195

Great color, a great price and terrific styling potential from Jack Erwin.

The Jack Erwin Adam Wingtip Oxford was first seen back in this blog’s round-up of stylish men’s dress shoes, and they make a return here as yet another example of why it pays to invest in high-quality, versatile footwear. Jack Erwin has made a name for itself in the digital style game thanks to its pricing and quality, and the Blake construction and reinforced stacked heel add even more durability to this particular pair. If you go the more casual route, they’d be equally at home with some dark denim and a navy blazer.

The Belt: J. Crew Factory Reversible Leather Belt in Brown — $22.50

Two belts for the price of one, plus a color that matches nicely with the rest of the outfit.

Sometimes, it can certainly be the right move to invest in an expensive belt — especially if you’ll wear it a lot. Other times, you need a reliable piece to get you from Point A to Point B in style and at a cost-effective price. That’s where this J. Crew Factory Reversible Leather Belt comes into play. You get two belts for the price of one, plus decent quality and a solid dark brown color that’ll match up sharply with your watch and shoes.

The Watch: MVMT Watches The 40 in Blue/Brown Leather — $120

Simple, refined and easy to wear with a suit.

As you put together stylish ensembles that fit in a variety of situations, it pays to look toward style essentials you might already have — like an eyecatching leather watch. This timepiece from MVMT Watches was reviewed just last week on the blog, and it’s a definite winner. The case diameter hits the sweet spot as far as a dress-casual watch, the quality is on-point for the price and the style potential is excellent (the blue dial will again really pop against the darker colors in this outfit). It can even work with a more casual outfit (again, the dark denim and navy blazer combo suggested above).

The Socks: Tommy John Solid Over-the-Calf Dress Socks — $16

Over-the-calf dress socks — an underrated style hack that makes a difference.

Dress socks, especially ones in a solid color, tend to get overlooked when lots of companies are incorporating pattern and color into so many pairs. But sometimes, you just want (and need) a simple, comfortable set of socks that’ll stay up and mesh nicely with the rest of your outfit. Tommy John socks solve that age-old problem of a pair sliding down throughout the day, and the dark navy color won’t distract from the neutral charcoal suit and solid shirting. Plus, they’re made of a lux Pima cotton blend with a hint of stretch.

The Extras: Tommy John Cool Cotton Trunk — $29

Style’s in the details, right?

Need I say more?

So that’s your head-to-toe Valentine’s Day look, incorporating some solid, versatile style, neutral colors and sharp accessories. Pieces like the above can work in lots of different situations while providing a change of pace from style staples you might already own — and when planning for as big of a day as Valentine’s Day, details like the right tie and pocket square can certainly prove essential (look good, feel good, right?). If you’ve now settled on your outfit but still need a Valentine’s Day gift suggestion, we’ve got you covered there, too. And should you have any last-minute questions, feel free to leave a comment below or send me a tweet.

What ensemble will you be rocking on this Valentine’s Day? What do you think of the above suggestion?

The Style Guide

All the best men's style essentials you need, every day.

Tag / men’s valentine’s day style

Style Suggestion: What to Wear On Valentine’s Day

Style Suggestion: What to Wear on Valentine’s Day