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. To the long-time readers of this corner of the web… a tieless suit is pretty familiar. But just because it’s been done before doesn’t make it the wrong play. If you’re headed to a dressed up affair, whether it be a work holiday party or New Year’s, one way to look more dashing (while dashing through the snow) and less like you just walked out of a job interview, is to lose the tie. Balance that lack of a tie with a pocket square with a little visual interest, as well as with a more casual/substantial watch, and you should be good. Going for a Danny Ocean meets James Bond meets approachable but still smart-guy look here. Is it a little, perhaps, “plain”? Sure. But the point is to let the person inside the clothes do the impressing, while everyone else is getting sh*tfaced on eggnog and wearing blinking nose Rudolph sweaters.

The Suit: Suitsupply Napoli Dark Grey – $399. Can a conservative suit be sexy? Sure can be. Slim cut, timeless lapels, and really nice fabrics. Half-canvas and ships and returns for free.

The Shirt: Nordstrom Tech-Smart Trim Fit Stretch Solid Dress Shirt – $69.50. Or, whatever your favorite crisp white (and comfortable) dress shirt happens to be. Whether it’s a spendy sucker like Ledbury, or something cheap from Amazon, make sure it’s clean, ironed, and ready to go.

The Collar Assist: Alloy Collar Stays – $10.95 (for a box of 36). Obligatory reminder for going tieless. Much more effective than the cheap plastic stays your shirt comes with. Put a slight bend in em’ for a perfect collar that’ll frame your face.

The Pocket Square: The Tie Bar “Domino Paisley” – $10. Dark blue pattern on a light blue background. Goes great with the charcoal suit and the white shirt while being anything but boring. I like folding mine and having the edge, with the corners pointing to my left shoulder, just peeking a bit out of the pocket.

The Topcoat: Amazon Buttoned Down Italian Wool Cashmere Overcoat – $279. Amazon’s own house menswear brands (Buttoned Down and Goodthreads) have been making some serious noise lately. This Italian wool/cashmere blend 2/3 roll button overcoat is just the latest offering. Ships and returns for free, but you have to have Prime to get it. More topcoat options can be found here.

The Scarf: Nordstrom Colorblock Cashmere Scarf – $66.66 ($99). Coordinates perfect with this setup. 100% cashmere. Ships and returns for free.

The Gloves: Barbour Dark Brown Leather Gloves – $59.63 ($89). Simple without being boring. Fleece lined. Nice strap at the wrist.

The Watch: Seiko Automatic “Samurai” in Blue and Gray – $312. Or whatever your favorite Diver happens to be. But I really like the Samurai here. Perfect for grabbing a little (but not too much) attention in an otherwise super simple, clean and mean outfit. Omega Seamaster looks on a budget. And you still get the incredible build quality and dependability of Seiko.

The Shoes: Spier & Mackay Box Calf Medallion Toe Oxfords in Dark Brown – $298. Just enough flash. And yes, you CAN wear dark brown shoes with charcoal pants and or suits. Light brown shoes won’t work, but a rich dark brown absolutely will. Ships and returns for free if it’s your first suit, sportcoat, or shoes purchase from Spier.

The Socks: Nordstrom Over The Calf Wool Blend Socks in Charcoal  – $14.50. Always. Forever. Some of the best socks on the market.

The Belt: Marino Ratchet Belt in #37 Brown – $27.99. Get comfortable where you can. Super precise, easy to adjust on the go, and looks like a regular ol’ belt at a glance.

Coming up tomorrow: A style scenario for a smart-casual party. Not quite as dressed up. Then we’ll move on after that to a much more dressed down/laid back style scenario for a holiday get together…