Cute Travel Outfit Ideas To Have On File For the Holidays

There’s a certain sort of magic that comes with traveling for the holidays. Packing up thoughtfully wrapped gifts and cozy clothes before embarking on a mini adventure is part of what makes this season feel so festive. Whether it’s by plane, train, or car there are a few things to keep in mind while crafting an outfit. “When traveling, multi-functional items make your look less fussy and your suitcase lighter,” White + Warren President Catherine Morrissey tells TZR. The brand celebrated the 25th anniversary of its cashmere travel wrap last year, an icon among those in the industry and a staple travel companion for Morrissey. “The wrap functions as a chic scarf while on the go, and as a throw for over a dress in the evening. On the plane, it’s a cozy blanket, or the children’s pillow.”

If your journey is by car or train, there’s a bit more flexibility with your travel looks as layers can be piled on and peeled off with ease, and there’s less shuffling around than at an airport. On the plane, as you know, every square inch counts (especially if you booked your flight late and are stuck in a middle seat). “My co-founder Kathryn and I always make sure to have a few chic ‘plane outfits’, as we call them, on hand,” Hilferty says. “To qualify as a plane outfit, the piece or set is usually a cozy knit that will not wrinkle and will still look chic and put together after [the flight].” She also points toward comfortable footwear as a precursor to holiday gatherings. “I love the idea of slipping on a furry Birkenstock for the plane ride and changing into a fun heel like Loeffler Randal's Rivka Knot Platform to party as soon as you touch down.”

Ahead, five practical and stylish combinations to keep in your back pocket as the season unfolds.

The Anchor Layer

As touched on before, an oversized scarf can moonlight as a chic travel wrap, keeping your neck and shoulder toasty on those unpredictably chilly flights. Team yours with a leather blazer and wintry white separates, like a classic cotton tee and cream-colored jeans. To make your outfit pop, find a scarf in a bright, seasonal hue like emerald green or cranberry red.

Sweater Weather

On the other hand, if you’re not in the mood to wear a scarf you can rotate in a sweater to get the job done. This cold-weather styling trick works especially well for those on the go because it adds flexibility to your look and lightens the weight in your suitcase (plus, it looks effortlessly cool, if you’re into that kind of thing). Layer your knit over a khaki trench coat and slouchy trousers and finish the look with a bold suitcase.

Crafty Chic

Comfort is key when coming up with a travel outfit, sure, but there’s still room to let your personality shine through. For an I just threw this together kind of vibe, begin with a relaxed base like a soft jacket and wide-leg pants. Then, bring in some unique pieces like a colorful baseball cap, chunky flats, and a bright bag. (Pro tip: If you are wearing the sandals below in chilly weather, add in some snuggly camp socks.) It’s cozy enough for a long haul flight but still reads as interesting.

Throw On & Go

If your MO is clean and classic for holiday travel style, then don’t overthink it — wear your favorite denim with a timeless trench coat and a lightweight knit layered underneath. On the accessory front, slip into your favorite pair of sneakers and top off the look with a polished handbag to tie the outfit together.

PJs, Please

While transiting in your red-and-green flannel pajamas probably isn’t the best idea, a chic silk PJ set is another story — particularly if your destination is reachable by car. This duo, paired with a polished handbag and flats, feels like a festive nod to the season. Plus, you can layer a long coat on top if it’s chilly out.