Dressing to impress for the holidays is an essential part of returning home.

November 14, 2025

Your Return-Home Wardrobe Game Plan

Whether you’re catching up with old friends or dodging nosy relatives, these outfits have you covered.

It’s November, and you know what that means, right? Time to start booking those flights (before they cost as much as your rent) and make your annual pilgrimage home for the holidays. Whether you visit a few times a year or only show up when the turkey hits the table, it’s always nice to see some familiar faces — and maybe even the family dog still remembers you.

Between toggling tabs to find the cheapest flight and deciding if you can survive without renting a car, there’s one thing you can’t overlook: your wardrobe. You’ll need pieces that can flex for any occasion. Think heavy knits you can throw over a T-shirt or oxford, a solid pair of jeans, and maybe even some dress slacks — because you never know when someone will suggest catching a play or hitting a nice dinner spot.

We’ve put together three outfit ideas that’ll have you feeling right at home — whether that’s grabbing drinks with old friends at a dive bar, surviving a chaotic gift exchange, or dressing to impress for family dinner. Consider this your style playbook for looking sharp when you head back home.

Built for Beers, Pool Cues, and Peanut Shells:

I don’t think there’s another item of clothing more ready for a dive-bar meetup with friends than our Cheval Hay Sweater Polo. It’s a warm, 100% cotton knit with a full placket — meaning you can toss it over a tee, layer it with a button-down, or even stack it on top of another sweater (like our trusty rollneck) if you’re really committing to the cozy look.

And since you’ll probably be shooting pool and wading through a battlefield of peanut shells, pair it with some light-wash jeans — durable, comfortable, and forgiving when the jukebox demands a dance move or two. 

Our Cheval Hay Sweater Polo is a perfect statement piece.

How to Win the Gift Exchange (and Best-Dressed Guest) Award:

Exchanging gifts at your friend’s house is always a good time — especially when things heat up during an intense white elephant game followed by a cutthroat round of Uno. Now, here’s the move: show up with a gift in one hand and something thoughtful in the other — like a bottle of wine or a dish to share. That way, if the snacks aren’t hitting, you can fall back on your own contribution — guest hack 101.

As for the fit: go for a long-sleeved merino wool polo, buttoned all the way up, paired with grey wool trousers. It’s the perfect balance — polished enough to show you care, but not so formal that people think you came straight from a job interview.

The muted tones of the Retro Diamond Cafe Polo are ideal for autumn.

Surviving the Holiday Interrogation in Style:

Now’s the real reason you booked that expensive flight. Time to prepare for cousins you haven’t seen since the last holiday, uncles debating the difference between “cooked” and “chopped,” and grandparents conducting a full FBI-level investigation into your love life.

It’s no small task — but at least you can control what you wear while navigating these family interrogations. A shawl-collar cardigan is the next best thing to wearing a suit jacket, minus the stiffness. Layer it over an oxford shirt, pair it with dark-wash denim, and finish with black loafers. And if you’re trying to dodge those “so, what do you do now?” questions, throw on a necktie. The room will assume you mean business — and no one will dare start pocket-watching.

A graphite shawl cardigan is a staple layer to add to your wardrobe.

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