The Holiday Season

A Man's
Dressing Guide

The holidays can be all over the map when it comes to dress code. But for men of style, there's more to seasonal dressing than those quasi-ironic ugly sweaters. You want a wardrobe that can handle whatever is thrown at you this time of year—from slush and snow to an avalanche of exhausting nog-and-punch socials. Whether it's a fancy affair with people you're hoping to impress or something more low key with family and friends, here are four outfits suited to the festivities.

Holiday Parties

Here's a tip for all holiday parties: you'll never regret staying sober or dressing well. Don't be the guy who drunkenly says something you can't take back on Monday morning. And perhaps just as disgraceful, don't show up in a santa hat. Just add a shot of holiday cheer to your standard business casual look. A textured wool blazer over a plaid shirt (perhaps dressed up with a wool tie), finished with a luxe scarf, is festive without making you look like part of the decorations.

Clockwise, from top left: Flannel pants, $325 by A.P.C.; Wool blazer, $350 by J.Crew; Checked shirt, $59.50 by Brooks Brothers; Cap-toe boots, $220 by Jack Erwin; Cashmere scarf, $99.50 / $69.90 by Nordstrom

The Family

When it's just your family and friends, you don't have to go out of your way or get too dressed up. But it's also a great time to swap a plain sweater for something textured or graphic. Like this hand-knit Intarsia Fair Isle sweater. Throw it over a T-shirt with some washed and worn-in jeans and a pair of boots and you're set. Top it with a camel overcoat and you look at once incredibly classic and very much right now.

Clockwise, from top left: Washed jeans, $95 by DSTLD; Camel top coat, $121 by ASOS; Hand-knit Fair Isle sweater, $198 by Bonobos; Hammered copper cuff, $40 by Cause and Effect; Commander chukkas, $150 by Sperry

Christmas Morning

You don't have to "get dressed" exactly, but you should look presentable. Opt for some ultra-soft tailored sweat pants and you'll look sharp, but still feel like you're between the sheets. A comfortable henley is a step up from your standard T-shirt and some graphic socks finish off the look. Just make sure to brush your teeth before tearing into the presents.

Clockwise, from top left: Tech fleece sweatpants, $100 / $79.97 by Nike; Marled henley, $62 by Flint and Tinder; Charcoal socks, $37 by Mr. Gray; Electric toothbrush, $65 by Goby

New Year's Eve

The turtleneck is having a moment right now, and it's the best not-too-dressy, not-too-casual alternative to the everyday shirt-and-tie combo. Plus, a sweater's a whole lot more flexible. Meaning as you start dancing (and posing for photos, let's be honest), you'll be a lot more comfortable.

Clockwise, from top left: Wool check suit, $499 by Suitsupply; Fisherman turtleneck sweater, $225 by S.N.S. Herning; Leather Chelsea boots, $178 by Banana Republic; Classic watch, $249 by Daniel Wellington


This Friday, "Office Christmas Party," starring Jason Bateman, Jennifer Aniston, Kate McKinnon and TJ Miller opens.