Style Suggestion: What to Wear to Your Holiday Party

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.

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.

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.

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: Tan Plaid Brussels Tie ($25) and Florence Pocket Square ($10)

A plaid tie and a floral pocket square? Give it a try.

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.

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.

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!

Style Suggestion: The Holiday Party

How do you take your martini, Mr. Bond? (Just don't hit 'em too hard at your holiday party).

How do you take your martini, Mr. Bond? (Just don’t hit ’em too hard at your holiday party).

With the arrival of December comes an occasion some of us definitely look forward to, and others tend to dread – the holiday party.  Depending on where you work or where you’re invited, it might be lots of fun… or decidedly not-so-fun. The same goes for holiday parties with family and friends – although hopefully those are enjoyable. And regardless of the situation, it behooves you (yes, I just used that word) to clean up appropriately. Plus, dressing up smartly can be quite fun – especially when you change up just a few things from your co-workers or friends (like fit and color/texture combos) and end up looking like a  million bucks (or at least deserving of that bonus). What follows is a suggestion that can go either CEO-level dressy for a fancy holiday party, or a bit toned-down for slamming some nog at a friend’s house (people do that, right?).  Stand by for further style suggestions later this month covering both a laidback Christmas and a more dressed-up Yuletide celebration. Enjoy, and happy holidays!
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The Overcoat: Combatant Gentleman Navy Wool Overcoat — $120

A versatile navy color, a slim fit and a great price make for a terrific top layer.

A versatile navy color, a slim fit and a great price make for a terrific top layer.

Before we get into what to wear for the rest of your night, let’s assume it’ll be cold before you get into that party — and let’s assume you’re in need of an outerwear revamp. There’s no denying the style power and versatility of a great topcoat, and this navy wool overcoat from Combatant Gentleman fits the bill perfectly. Its price is more than solid, and for a new introduction to the brand, it would seem that the quality should be on-point from past experience. The fit looks to be trim yet workable over a suit, and the soft Italian wool should also be workable for that pricepoint. The navy color is going to work with all kinds of outfits outside of this particular occasion, as well.

The Suit Or Sweater: Combatant Gentleman Charcoal Birdseye Slim Fit Suit — $200 OR Frank & Oak Merino Cardigan in Bitter Chocolate — $70 And J. Crew Factory Thompson Slim Voyager Suit Pants — $84

Two options, one dressy and one more casual -- but both affordable.

Two options, one dressy and one more casual — but both affordable.

So Combatant Gentleman is the pick for our suiting option as well, but not just for kicks. The brand has made its mark in the affordable tailoring realm, offering up solid picks for more-than-agreeable prices. Its blazers, while not 100% perfect, are also an extremely great value for the price. So picking up one of its charcoal suits can knock out two birds with one stone – if you’re in need of a first-time suit on a budget, or if you want to refresh your suiting game for not a lot of dough. This birdseye suit is a nice visual departure from a flat charcoal color, too. If the occasion doesn’t call for a suit, you can swap in a crisp, slim Frank & Oak cardigan (much sleeker than a thicker shawl number). That can then be paired with some navy wool trousers and accomplish the same goal. Of course, dark denim can be swapped in with your cardigan for an even more toned-down look.

The Shirt: Standard Shirt White Dress Shirt — $59

Take your pick of two collar styles, both for a tremendous price from Standard Shirt.

Take your pick of two collar styles, both for a tremendous price from Standard Shirt.

While it’s worth looking at a site like EXPRESS for its shirt deals, there’s not a shirt that offers a price-quality ratio quite like Standard Shirt; that makes sense given that two styles of white dress shirts are all the company does. And they combine that quality with smaller touches (like a wider, suit-ready collar) in an inexpensive package. I threw on the brand’s spread collar shirt for a rather sweltering Michigan wedding and was also pleasantly surprised with its breathability. The crisp white shirt is definitely going to be a great anchor for either the suit or cardigan any way you look at it.

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

A tie with some visual interest to complement the birdseye weave of the suit.

A tie with some visual interest at a low price.

If you need to ditch the tie in favor of just that slim cardigan or tailored charcoal suit over a crisp shirt, that’s the way to go. But if you do still need that tie, The Tie Bar, as always, has you covered. While a navy knit tie could also be a good, versatile buy in this case, a grenafaux tie brings that same amount of texture and visual interest while looking a bit more suit-ready. And in this case, the texture of the tie will bring a bit more punch than a standard silk number, allowing it to stand up to the birdseye suit nicely.

The Pocket Square: General Knot & Co. 1940s Crimson Duck Pocket Square — $38 OR The Tie Bar Light Champagne Herringbone Pocket Square — $10

Take your pick of either vintage fabric and a higher price, or an old standby in a nice fabric.

Take your pick of either vintage fabric and a higher price, or an old standby in a nice fabric.

So we have two pocket square options here – one that’s flashy and conversation-worthy, made from vintage fabric, and one that’s still conversation-worthy, but mainly for the punch of pattern and color it brings. When your suit and tie both have some texture, throwing in another dash in a contrasting color still works, mainly because of that color difference. Either would add a bit something extra to your suit that a solid white pocket square might not (although that works with this outfit, too). While the price for the General Knot square is a bit of a splurge, keep in mind that if you go cardigan-only, you save that cash.

The Shoes:  Johnston & Murphy McGavock Wingtip Boot — $250

A dressy wingtip boot with seasonal fabric design touches to stand up to the chilly weather.

A dressy wingtip boot with seasonal fabric design touches to stand up to the chilly weather.

Johnston & Murphy can sometimes be a bit overlooked what with a company like Jack Erwin competing right in its wheelhouse, but the brand delivers on seasonal numbers, like these mixed-media boots. They’re the perfect middle ground for stomping through some snow or rain to get into that party, yet they still look crisp, slim and appropriate for tailored wear. There’s a touch of brown in there on the sole, but that won’t look too out of place next to the charcoal suit. If funding is tight, JC Penney’s classic Stafford Wingtip is going for a right steal now. Either way, black shoes can look especially sleek this time of year (and if SPECTRE is any indication, black shoes are going to be the way to go for the months ahead).

The  Belt: EXPRESS 2-in-1 Reversible Buckle Leather Belt in Black — $39.90

Two for the price of one, with a crisp look to boot.

Two for the price of one, with a crisp look to boot.

EXPRESS’ quality might sometimes be suspect, but when you need a belt (or in this case, two belts) at a decent price in a pinch, a reversible option never hurts. They do all kinds of belts, but this is a sharp, sleek pickup that’ll go well with those crisp black shoes and the dialed-in black watch (more on that below). You can always go beltless if you find that’s more sleek, however.

The Watch: KOMONO Winston Regal in Black — $99.95

Super-crisp style for under $100.

Super-crisp style for under $100.

KOMONO’s at it again – this brand flies under the radar occasionally, but its dressier watches are just as solid a value as its more casual, seasonally focused timepieces (like the Winston Herringbone timepiece I reviewed earlier this fall). The Winston Regal in Black is super-sharp, and the thin case and no-nonsense dial fall right in line with the sharp pieces in the rest of this ensemble, from the black boots to the crisp white shirt and black belt. And at under $100, it’s an excellent steal on a budget.

The Socks: American Trench Dress Rib Sock in Cloud Grey — $14.50

High-quality socks that'll be worth more than the price tag.

High-quality socks that’ll be worth more than the price tag.

Whereas we’ve dialed it back with the suit and watch, these socks tip the scales more in terms of price. American Trench is a Style Guide favorite (check out more on its socks here), and there really isn’t a brand doing made-in-America socks as well as they do. So in this instance, it makes sense to splurge on some high-quality dress socks that can stand up to repeated wear with a workhorse charcoal suit; while socks with a pop of color are an option too, you might be pleasantly surprised at how sharp a sock looks when matched with a trouser (especially in a clean charcoal-on-charcoal combo).

While it can be a bit off-putting to see so many dark colors in an outfit, from the suit to the pocket square to the shoes, belt and watch,  it can be refreshing to go sleek, simple and yet still put-together. Plus, other cold-weather occasions leave plenty of time for working in colors, and each of the above pieces can be mixed and matched into those outfits as well. So go sharp this holiday season and see where it takes you. Once again, enjoy and let me know your holiday outfit picks below.

What do you think of the above ensemble? Will you be going dressy or casual this year at your holiday party?

Ben Sherman US