#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

The Friday Read: Valentine’s Day, Ryan Reynolds and Harry Potter and the Cursed Child

Editor’s note: Expect these posts once a week on Fridays — consider this a jumpstart on reading for your weekend downtime. Expect a mix of style and non-style content. For more entries, click here

While last week was a big one (for me, at least), with the second iteration of  #NYFWM, perhaps this week has been a big one for you. After all, Valentine’s Day is upon us! What are you set to wear? Here’s your Valentine’s Day style suggestion. And do you have a gift all sorted out? If not, best get to it with these Valentine’s Day gift suggestions for that special someone. And if you have all of that in order, congrats! Enjoy what’s hopefully a three-day weekend! But before you get going on that last-minute shopping and outfit wrangling, catch up on some menswear (and yes, non-menswear) news. I won’t bug you for too much longer — after all, there are gifts to buy! Look for a Monday product review covering the standout Color No. 8 Diplomat Boot from Thursday Boots, followed by another sharp #OOTD entry and of course, the usual weekly content here at The Style Guide. Stay stylish!

  • This could come in handy in advance of Valentine’s Day, as GQ offers some standout layering tips courtesy of Ryan Reynolds — huge fan of that electric blue cardigan.
  • It might not quite be spring yet, but Apolis still is offering up its Civilian Travel Suiting bundles for a nice deal — within the higher-end market, that is.
  • Get away on a tropical vacation (or at least, start dreaming of one) by checking out the first in a series of global travel and adventure videos from the fine folks behind lifestyle brand Reef.
  • Long(ish) Read of the Week: Harry Potter fans, rejoice! Unless you’ve been living under a rock (apologies if so), Time and others have reported that the script for Harry Potter and the Cursed Child — the play, that is — will be published in book form later this summer, and released, fittingly enough, on Harry Potter’s birthday! So exciting.

Frank & Oak

On the hunt for more to read? Look right here.

    • The newly revamped VOUCH Mag is up-and-running in a big way — check out my latest feature on the best boots to survive winter, and keep an eye out for some brands you might recognize.
    • Here’s a new one, too — never lose your umbrella again with the BLUNT + Tile Traceable Umbrella; it was neat to learn more about it for GearHungry.


Style Suggestion: Valentine’s Day

The day is almost upon us — a holiday to celebrate being with someone you love that also happens to bring up questions on what to do if you’re on your own. In that vein, Dappered has a great series running this week covering 3 different outfit scenarios — out on the town with a loved one, staying in for a date at home with your significant other, or staying in on your own; all terrific picks for each situation. But for this particular post, we’ll cover an idea on how to get dressed for a classy date out and about — whether it’s just down the road or a jetset across the country. Check out the picks below.

The Suit: J. Crew Factory Thompson Voyager Suit Jacket — $238 and Pants — $138

A basic navy in an easy-to-move fabric that'll look classic and sharp.

A basic navy in an easy-to-move fabric that’ll look classic and sharp.

J. Crew Factory recently launched their own set of travel-ready suit separates, very similar to sibling store J. Crew’s Traveler suit launched last year. In the case of J. Crew Factory, it’ll be tough to top their Thompson suit separates (which have gotten fantastic reviews), but these appear to be in a similar vein — a nice and relatively trim cut and this time, fabric that moves easily and (hopefully) doesn’t wrinkle too readily. In the case of this outfit, a navy suit is as classic as it gets for a sharp night on the town — it also acts as a neutral base while still looking different than a traditional black suit. Fortunately, plenty of sizes are available in both the pants and the suit jacket. If the occasion calls for something less formal than a suit, a great navy or charcoal blazer from a more affordable brand (like one of Uniqlo’s pieces here) would look right at home with some slim tan chinos.

The Shirt: J. Crew Factory Thompson Dress Shirt in End-on-End Blue —$54.50

Blue that's just different enough thanks to the end-on-end texture.

Blue that’s just different enough thanks to the end-on-end texture.

For the shirt pairing, we stick with a frequent theme in men’s style it seems, and pair different shades of blue together. However, that’s not always a bad thing — in this case, this particular shirt is less stark and more suited for winter than a white dress shirt; it helps bring some depth to the outfit as well thanks to the end-on-end texture. Thompson dress shirts are an excellent budget pick (as outlined here) and play nicely off the deeper navy of the suit in this instance. When paired with the grey tie from below as well, the shirt acts as a cooler-colored anchor.

The Tie: The Tie Bar Grey Wool Herringbone Tie — $15

Taking a traditional suiting pattern and turning it into a tie.

Taking a traditional suiting pattern and turning it into a tie.

The Tie Bar has long made ties that are an excellent value — and great quality for the price, too. Their options can be overwhelming at some times, but it seems their seasonal ties are some of the best in the business — and for dozens of dollars less than larger outlets, too. This wool herringbone tie is a winter twist on a fabric and pattern normally reserved for blazers. It’s not shiny at all compared to regular silk ties, so it blends in better with heavier cold-weather textures. And there’s good contrast between the navy suit thanks to the herringbone pattern. A silver knit tie could also serve the same purpose in terms of texture while offsetting the suit more, however.

The Pocket Square: The Tie Bar Solid White & Red Tipped Cotton Pocket Square — $8.00

Paying homage to the holiday with a subtle accessory.

Paying homage to the holiday with a subtle accessory.

While you could go all out and don something outrageously red here, sometimes subtlety is the best policy. In this case, the very slight red of the pocket square (which should just be peeking out of your jacket, at any rate) nods to Valentine’s Day without going overboard. Even better, it pairs well with the dark navy suit, blue shirt and grey patterned tie without throwing off the outfit at all. The price is, of course, tremendous for an accessory from The Tie Bar.

The Shoes: Stafford Logan Wingtip Oxford — $39.99

A classic wingtip shape at an unbeatable price.

A classic wingtip shape at an unbeatable price.

That’s right — $39.99 on clearance right now, with quite a few sizes left (if you’re a 12 or 13 though, you’re out of luck). These shoes first came recommended here for their looks and budget-worthy price, of course. If sizes do run out, you could always reach for a slightly lighter shade of brown from the same maker. Dark brown is a good pick in this case because it echoes the darker shades of winter while standing out quietly. Even in a dark brown, it’s less traditional but nearly just as sharp as a black shoe. It also plays off all the other shades in this outfit — from navy, light blue and grey to red. On another note, if a dress shoe won’t work given the weather, a thicker wingtip boot with a grippy sole could strike the same balance in the outfit.

The Socks: J. Crew Ribbed Stripe Socks — $14.50 

The ribbed texture and simple stripes on these socks go a long way toward their versatility.

The ribbed texture and simple stripes on these socks go a long way toward their versatility.

This particular pair of socks has gotten recommendations across the board in several different types of outfit scenarios on this blog, and with good reason — they’re a nice in-between blue color that plays off the navy in the suit while still adding a bit (but not too much!) pattern. Much like the pocket square, they also work nicely in tandem with the other colors in this outfit. At the same time, they’re not too rugged, like these similarly-priced striped socks might be

The Rest: Breda 1680d Watch in Brown Leather — $59; J. Crew Factory Plaque Leather Belt — $23.50

Brown leather on both the wallet and watch, to match the shoes. A camel topcoat to finish things off.

Brown leather on both the wallet and watch, to match the shoes.

For these two accessories, the obvious color choice is brown given the deep brown color of the shoes. The watch by Breda is slightly less minimal than a similar brown-leather Stuhrling option for about the same price, but the white dial and grey numerals help keep things crisp and clean. J. Crew Factory’s plaque belt is the brand’s appropriately dressy take on a similar option from J. Crew, yet for about half the price. Both pieces would be good pick-ups as part of either a watch or belt rotation, and since that J. Crew Factory belt is decidedly slick, it would work well at the office or on business trips, too.

To finish off this whole outfit, other accessories are key — a great topcoat is an awesome finishing piece that serves an essential function in cold weather  — Stafford’s signature topcoat  has a decent number of sizes and colors left (that camel option would be a rich, luxurious-looking outfit topper for a great price). Warm, sharp gloves in black leather surely wouldn’t go amiss, either. Appearances can certainly go a long way in making the night a great one, but don’t forget about a great gift (and your time and attention!) either!

What are your plans for Valentine’s Day? What will you be wearing?