Style Scenario: What to Wear to a Dressed Up Holiday Party

What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. It’s holiday party season (maybe), and we’re going to tackle three style scenarios in the coming days depending on how swanky the party you’re headed to happens to be. This one is for looking pretty darn sharp. Not tuxedo-fancy, but the occasion calls for getting dressed up. We’re going for Clooney levels of cool here, minus the Armani price-tag. Inspiration for this outfit comes from Black Watch Tartan, which is a holiday staple, but the outfit doesn’t actually use the pattern itself. I know. Wild. 

The Suit: Suitsupply Dark Grey Glen Check Italian Wool Suit – $399. Glen Plaid is not Black Watch Tartan. But that’s the point. We’re calling out bits of Black Watch without going full Black Watch. So a subtle, tonal pattern here delivers just enough visual interest, while still remaining all sorts of dark and handsome. This suit just hit their site, and it’s already close to sold out. Your favorite solid charcoal or dark gray suit would also work here. Use what ya got, right? And if you DO go with a solid suit, that means you could work in some sort of patterned pocket square instead. But fingers crossed for a restock on that SuSu dark grey glen check. That thing is something. And if it sold that fast, you gotta think they’d restock, no?

The Shirt: Rhone Commuter Shirt in Navy – $118. Rhone’s commuter shirts are game changers. Made from soft, stretchy, temperature regulating and wicking tech fabric, they make cotton dress shirts feel like they’re from the dark ages. And that’s perfect for a dressed up holiday party that could be unpredictable and higher stress. But these shirts do have two drawbacks (aside from the stratospheric price): Rhone can’t keep them in stock (found these at Backcountry of all places), and… the collars are a little small for dressed up wear. They lean smart casual, but in this instance, they’ll do fine (see an example of how this navy commuter shirt looks with a suit, right here). Hidden button down collar points are a huge plus too. Want something cheaper? Try this from Charles Tyrwhitt.

The Pocket Square: John Henric Dark Green Grenadine Pocket Square – $29. Thus completeth the Black Watch inspired color trifecta. Textured grenadine fabric here. There’s always this cheaper silk-twill from TheTieBar if you want to save a few bucks.

The Watch: Orient 2nd Gen Bambino V III Automatic – $132. AKA the Bauhaus. Keep it slim and dressy. Shelve the chunky sport watch on a night like this.

The Shoes: Allen Edmonds Carlyle Oxford – $296.25 ($395). The Carlyle manages to be simultaneously dead simple and eye-catchingly contemporary. That’s a neat trick. Whatever simple black oxfords you own will work here. A cheap option would be the BR Kevin Cap Toe, assuming you can nab them on sale. They often drop to $100 or less during sales.

The Belt: Marino Men’s Comfort Click Ratchet Belt in Dark Charcoal – $18.99. Even the nicest holiday parties can be uncomfortable dumpster fires (just ask anyone who has ever worked in HR). So staying comfortable is the name of the game. And a ratchet belt that looks just like a regular belt, along with the tech-fabric dress shirt and breathable wool suit, make for a hard to beat combo.

The Socks: Made in Italy Taylor Stitch Merino Socks in Charcoal Dot – $22.50. Dots and plaid? Dots and plaid! The dots are spaced out enough that they won’t clash with the close, condensed lines of the Glen check on the suit. That and they’re super comfortable.