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, and we’re going to tackle three different style scenarios in the coming days, each 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.

The Suit: Suitsupply Dark Grey Italian Wool Suit – $499. Or whatever your preferred gray or charcoal gray suit happens to be. Just not a light summer gray. This particular one from Suitsupply is from their Wardrobe Starters line. Nice Italian wool fabric, half-canvas construction, and it ships/returns for free. Make sure you leave time for alterations to get that fit dialed in.

The Pocket Square: J. Crew Blackwatch Tartan Pocket Square – $49.50. The key to making an outfit holiday-appropriate without investing in a pair of velvet penguin pants is to wear a blackwatch or otherwise holiday-ready pocket square. This tartan one with a red border from J. Crew is darn near perfect. The Less Expensive Option: If you don’t have time to source a fancy pocket square, head to a fabric/craft store and find some blackwatch or otherwise holiday-ish looking plaid fabric. Fold your purchase so the unfinished edges are in your pocket, and the folded, softer edge is sticking out just a quarter of an inch or so. That is assuming you’re not handy enough to finish the edges yourself. Kudos to those who sew and even do their own alterations. It’s impressive.

UPDATE: Looks like J. Crew sold out of those pretty quick. Instead, try this dark tartan wool pocket square off Amazon if you need a quick/easy alternative. Ships fast with Prime.

The Shirt: Rhone Commuter Shirt in Black – $128. Yes a black shirt. A gray suit + black shirt has worked for a certain Mr. Clooney for going on two decades. And it’ll look great on you too. Especially in a room full of other folks donning chunky Christmas sweaters and workplace khakis. 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: First, while the hidden button down collars are a terrific feature, the collars are a little small/soft for dressed up wear. They lean smart casual, but in this instance they’ll do just fine (see an example of how this navy commuter shirt looks with a suit, right here). The second drawback would be how freaking expensive they are. They did go on sale during black Friday, but… The Less Expensive Option: Try this from Nordstrom for under $50, but it’s decidedly “un” techy. This other Nordy option for $79.50 is techy/engineered to stretch and breathe better, but it has a button down collar that’s very much not hidden.

UPDATE: Looks like Rhone sold out of the Commuter shirt in black over Black Friday/Cyber Monday. But it appears that Dillard’s (yes, Dillard’s) has some.

The Watch: Orient 2nd Gen Bambino V III Automatic – $130ish. AKA the Bauhaus. Keep it slim and dressy. Shelve the chunky sport watch on a night like this.

The Shoes: Nordstrom Dane Cap Toe Oxfords – $99.99. Having a pair of black oxfords is about as close to a “must” as it gets in menswear (there just aren’t nearly as many rules as others would have you think). Yet at the same time, most guys won’t wear their black shoes as much as their brown ones. Therefor, while they’re a “must,” you can cheap out on your black dress oxfords a bit since they probably won’t see frequent wear. Full review of the Nordstrom Dane can be found here, albeit in brown. Want to spend? Can’t go wrong with the Allen Edmonds Park Avenue. Want to hit something in between the Nordy budgets and the AEs? Try Spier’s new line of blake stitched footwear.

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.