It’s a cliché but it’s true: the holidays are damn stressful. Take that pesky “what should I wear” issue off your plate with these outfit ideas so you can have extra room for pie or whatever. Click on the titles to see our examples.

Here’s what to wear…

To the family dinner

Unless you’re a Rockefeller, your holiday family dinners are probably pretty casual. However, that doesn’t mean you should dress like a schlob. If you do, expect nosey questions from extended family that are pseudo-concerned you don’t have your “life together.” The idea is to strike a balance between conservative, stylish, and comfortable.

Tweed pants and an ultra-soft plaid button-down topped are both cozy and wrinkle-resistant. A luxurious cashmere cardigan is the perfect layer that you’ll wear again and again throughout the season. Impress your loved ones with your style prowess with The Poitier Double Monk Strap—the oxblood color ties in perfectly with the red tones in the flannel. And, of course, finish the outfit with a watch so you know exactly when it’s time to leave.

At the office party

 It’s everyone’s favorite part of the work year—so feel free to show out for the holiday office party. Impress everyone by showing them you’re hip to the latest trends and know how to coordinate beyond the suit ensembles you bring out Monday through Friday, nine to five.

Blue pleated trousers have a Gatsby-esque feel, and what could be better for a party? A diamond-patterned shirt is festive without going overboard and a classic grey sports coat elevates the look to be a complete outfit. The Martin Wholecut Oxford is the perfect pair of leather shoes to add polish and class and a matching belt ties the neutral marrone pieces together. Top it off with a simple navy pocket square for an added touch of class needed for an evening get-together.

While gift shopping

Love it or hate it—you’re probably going to have to pound the pavement a little to get the perfect gifts for friends and family. Try as we might, you can’t buy everything online. If you must brave the cold—and the mall—make sure you’re comfortable so you aren’t completely miserable.

Keep it easy with a pair of straight-slim dark wash jeans and a thermal Henley tee in a neutral like white. Keep warm with a fur-lined parka in army green and a simple black beanie that you’ll be sporting on the weekends throughout the winter. Finally, put on your Paul Evans High-Top Sneaker in Nero and the matching leather belt. You’ll look and feel good enough to make shopping less of a drag.

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