Can you believe the holiday season is upon us? Here at The Style Guide, we absolutely love the holidays — and by we, I mean me. From holiday travel to composing my Holiday Style Wish List, it’s an absolute treat of a time. In addition to looking forward to time spent with loved ones, you should also keep a weather eye out for ways to improve and upgrade your style — especially at this crucial time of year. Yes, it’s a time when you’re dealing with (likely) inclement weather, a bit (or a lot) of travel, gift-giving and plenty more — not to mention a work holiday party that often pops up when you might least expect it (or least look forward to it?). It’s also a time to make sure your style doesn’t stray into overly, err, holiday-esque territory — so, a reindeer sweater is overdoing it just a bit. To get you ready for that inevitable invite in fine fashion, we’ve pulled together one heck of a style suggestion — it’s a bit dressier than your everyday rugged favorites on this here blog, but you’ll be all the better for it. And as you’ll see below, it takes tried-and-true layers — like the classic V-neck sweater — and upgrades them with winter-ready shirting and accessories. Can’t wait to see it? Good. Me neither! Follow along on Instagram and Twitter for more daily style inspiration, and chime in on this suggestion via The Style Guide’s Facebook page.
The Topcoat: JackThreads Tieman Topcoat — $149
Smart, stylish, affordable and easy to wear with a suited holiday look.
Is it any surprise that the great team at JackThreads has absolutely knocked it out of the park with the Tieman Topcoat? It shouldn’t be — the brand’s menswear-focused revamp has been a welcome addition to the digital style scene across the past year, and this handsome, eye-catching double-breasted topcoat is Exhibit A in that regard. It’s no Canada Goose parka in terms of battling extreme conditions, but thrown on over a suit on a crisp winter’s night? You just might have the nicest jacket at the party, fella.
The Suit: Taylor Stitch Telegraph Jacket and Trousers in Grey Wool — $456
A refined suit made with premium materials for under $500? You betcha.
Would you believe that Taylor Stitch makes a heck of a beautiful fall and winter suit in addition to their classic chambray shirts and rugged slim chinos? It’s true, and that’s what makes the Telegraph Suit such a worthy pick-up. The brand took plenty of customer feedback and incorporated it into a suit that manages to merge the modern — a slim fit — with the classic — patch pockets and textured fabric. It’s a classic suit that’ll serve you nicely throughout the rest of the winter season — and it’s the right choice here because of its terrific fit and styling potential. It’s neither too stuffy nor too sloppy, and the Telegraph Suit is certainly a steal for under $500 via Huckberry.
The Sweater: J. Crew Italian Cashmere V-neck Sweater — $225
A slightly unexpected color that plays nicely off the blue shirt and grey wool suit.
There’s no question that J. Crew knows how to do luxurious basics well. Is $225 a lot for a sweater, as we always ask ourselves? Yes, it certainly is — but finding an Italian cashmere sweater for less than that is a bit of a difficult endeavor. The rich Heather Laurel color seen here is a great complement to the grey wool suit and darker blue shirt. Plus, it adds a bit of contrast to the tan plaid tie. Green and blue is a bit of a unique color combination, but it works here — and the sweater will keep you nice and warm underneath your Taylor Stitch suit and topcoat.
The Shirt: Cordings for J. Crew Shirt in Warm Twilight — $128
A dress shirt with some texture and a pleasing winter-ready color.
What better way to complement a classic winter-weight suit than with a sharp blue dress shirt in a textured fabric? J. Crew always seems to do an impressive job with its third-party collaborations, and the Cordings for J. Crew partnership is the latest addition to that roster. Cordings brings its own classic British sensibility to sharp tailoring, and that makes this shirt both traditional and modern. It’s the perfect complement to a deep green sweater — the combination is unique, but works with the darker tones of winter.
The Tie and Pocket Square: Ties.com Tan Plaid Brussels Tie ($25) and Florence Pocket Square ($10)
A plaid tie and a floral pocket square? Give it a try.
In keeping with the crisp cold-weather vibes of the season, we’re reaching for two pieces here that nod to the holidays without going full-on Santa Claus. The Tan Plaid Brussels Tie is affordably priced in a nice plaid wool that contrasts with the grey wool suit and blue shirt — it’s a bit of an unexpected color pairing. And the patterned blue pocket square plays nicely off the lighter blue shirt. You’re looking at two patterns that at first might not work together, yet up against a grey wool suit, the combination is a fresh, affordable one. Right?
The Boots: CAT Footwear Sutter Boots in Rust — $210
Just as ready to wear with a winter suit as they are with tough dark denim and a Henley.
Remember seeing the rugged, refined and tough-as-nails CAT Footwear Sutter Boot in this site’s post on the best men’s boots for fall? Of course you do. Although at first this 6-eye, burnished boot might seem too rugged to wear a suit, fear not. The rougher texture of the suit, shirt and tie lend themselves well to a durable, handsome boot. Plus, the higher cut of these boots gives you added traction and grip should the weather turn inclement. If you find yourself in a warmer climate? Ditch the boots for a pair of crisp leather wingtips and perhaps swap out the wool suit for some slim stone chinos and a lightweight navy blazer. Ya dig?
The Socks: American Trench Pima Cotton Houndstooth Socks — $23.98
American Trench consistently delivers on premium, American-made socks — that goes for both the brand’s casual varieties and dressier iterations. Take these comfortable Pima Cotton Houndstooth Socks — the navy pattern plays nicely off the blue shirt and grey wool suit, not to mention the patterned pocket square. They’re an investment for a pair of socks, but they’re one that’s worth it — you can wear sharp, subtly stylish socks like this with all sorts of winter work week outfits.
A classic, affordable dress belt and a go-anywhere watch.
Make no mistake, your Style Guide author is as much of a fan of classic dress watches from the likes of Daniel Wellington as you are. But given that we’re going with a more rugged outfit — from the textured shirt and tie to the grey wool suit and boots — a sport-inspired, tough chronograph fits right in. The great thing about the Armogan Spirit of St. Louis Chronograph
is the rich contrast between the black dial and brown leather strap — it’s a pairing that works surprisingly well together. Of course, you can never go wrong with an affordably priced J. Crew Factory leather belt fit for both business casual and slightly dressier looks.
So, that’s your Holiday Style Suggestion all sorted out. A slim V-neck sweater adds a bit of visual interest to a rich grey Telegraph Suit
from Taylor Stitch, and both the shirt and tie bring seasonally appropriate texture. The thing to keep in mind is that even at an investment-level price, the Telegraph Suit
is more than just a one-trick pony. That is, you can break up the jacket and pair it with Mott & Bow denim
and a classic white Oxford (plus, those durable Sutter Boots
from CAT Footwear) during the regular work week, too. And the handsome, refined Armogan Spirit of St. Louis Chronograph
is an absolute keeper in terms of both durability, style and versatile looks. Oh, and those Pima Cotton Houndstooth Socks
? Once you’ve tried socks from American Trench
, you might never go back. As always, you can’t go wrong with a refined, versatile JackThreads topcoat, either. Let me know in the comments how you’re dressing for your holiday party — and as always, stay stylish!