From an Upstate farmhouse to a sunlit beach, here’s how to dress comfortably during the busiest travel season of the year.

For most of us, Thanksgiving is one of those logistically demanding, travel-focused holidays that requires a suitcase full of polished, wearable outfits that can do more than one thing: a swimsuit that doubles as a bodysuit, a sweater that moonlights as an underlayer, or a shearling coat that can shield you from an indoor breeze or outdoor chill without looking out of place in either. Usually, these pieces have to squeeze into a carry-on, too And, while most scenarios lean more casual than party-ready, your outfit still needs to rise to the inevitable family photograph occasion that will likely be displayed for years to come. No small feat.

Whether you’re facing a long drive to a farmhouse, a flight somewhere warm, or a crowded restaurant, here are five outfits for five very different Thanksgivings.

1. Stay Warm (and Look Lovely) at a Drafty Upstate Farmhouse

If you’ve ever woken up in a nineteenth-century farmhouse in late November, you’ll know those bucolic surroundings are usually accompanied by a biting chill. If that’s the setting for your Thanksgiving get-together this year, an outfit that’s warm and elegant should be your aim. These Houndstooth Man Pants look right at home in the country, and since they’re generously cut from a soft jersey with a little stretch, are also perfect for a celebration that pivots around a feast. Balance out their bagginess with the Barely There Jersey Stitch Crew Neck, which works as both a fine sweater, or under layer for post-meal walks. A statement piece like the Shearling toffee-hued Coat will not only keep you warm, but it won’t raise eyebrows should you need to combat an indoor breeze at dinner (think of it as a tactile blazer). Finish with the lug sole Zip Front Boot, which can handle slippery gravel and creaking stairs with ease.

2. Light, Breezy Looks for a Sunny Family Getaway

If you’re among the many families braving JFK or a similarly crowded airport for a family-centered Thanksgiving escape, your suitcase will look a little different. Start with a sleek black swimsuit, your getaway’s answer to the LBD. Not only will it take you from a morning swim to lazy lunches by the pool, but it will step up at dinner, if you style it right, too. Treat it as you would a bodysuit and layer on the layered necklaces, then pair with loose trousers or jeans. For the main event—the holiday meal itself—try a lightweight matching set, like this softly striped shirt and skirt. Both breezy and preppy, it’s your photo-ready two-piece for Thanksgiving dinner in the heat.

3. The Family Reunion at a Restaurant

When the gathering is large, the logistics are complicated or the host is ready for a year off, a restaurant reservation makes for a stress-free family tradition. Enter our slouchy velvet suit in a deep berry hue. The relaxed tailoring leaves you free to enjoy every course, while the sumptuous fabric keeps your outfit elevated. Go for a shirt and heels if your setting leans more formal, or pair with a white t-shirt and sneakers to play the look down.

4. The Friendsgiving Outfit That's Cool and Comfortable

Whether you’re heading to a low-key potluck or a dressier sit-down dinner, you’ll want an outfit with easy polish. Loosely tuck the Relaxed Forever Shirt into the Leg Elongated Jean for a touch of menswear charm, then add the Stretch Boot to extend the lengthening effect of the crease-front jeans. They’re crafted from stretch-infused leather for a glove-like fit and are set on a flared block heel that won’t leave you wobbly. Finish with this mixed-metal layered ring set for a Parisian touch that will catch the candlelight when you reach across the table for another glass of wine.

5. The Airport Outfit That Takes You Straight to the Thanksgiving Table

For the busiest travel weekend of the year, you need an outfit that can handle the arrivals desk as effortlessly as the family table. Start with a jean that has a little give: the Ankle Length Skinny in a mid-blue wash can handle a cramped airplane seat and a second helping of dessert without causing discomfort. Dress them up with our fuzzy V-Neck in a smoky charcoal. The slouchy boyfriend fit is comfortable to travel in, while the stunning brushed cashmere effect is refined enough for a celebratory dinner. Finish with a roomy funnel neck leather jacket, which will hold its shape through every leg of your journey. As for the Everything Day Bag—it’ll slide under the seat in front of you and hold enough for an overnight stay.