Every Chic Thing I'm Packing for Winter Vacations

Everyone has a favorite aspect of the holiday season. Some people are all about the gifts, and others live for holiday decorations. But for me, it's the travel. I'll take just about any excuse to pack my bags for a weekend away with my best friend. And the only thing that sounds more fun than mapping out the trip is planning the outfits we'd wear during it. Hello, I'm a fashion editor—please don't act so surprised.

Naturally, the looks in question must be trend-forward and chic, but I'll also require some matching moments (whether my friend likes it or not). No matter how small my carry-on luggage is, one item that will always make the cut is Longchamp's Box-Trot handbag. It's the perfect, classic leather bag to complete every cool outfit I want to wear right now. It's no surprise that the French brand has mastered this style. Ahead, see how to style this editor-favorite accessory. (Airline tickets not included. Sorry.)

Wearing matching bags is just the right amount of coordination for a twin moment in all the photos I inevitably take on vacation. The Box-Trot comes in three sizes, all of which feature an adjustable crossbody strap, an especially convenient detail when running around a city all day. (I like to have my hands free so I can properly focus while shopping, but that's another story.) But my absolute favorite detail is the boxy shape—it feels both classic and modern.

The casual vibe of this sweaterdress and cropped puffer vest is perfectly suited for a tiny Box-Trot worn as a crossbody. I love the way the black leather and gold hardware stand out against the olive-green color of the knit dress. 

This look feels very "downtown city girl" with the plaid miniskirt, knee-high rubber boots, and oversize bomber, but the addition of the bag adds a polished touch. The green leather makes a bold and playful statement, especially when paired with matching green sunglasses, which are not required but very much encouraged.

These chic looks are a lesson in taking matching outfits to the next level. The coordinated plaid prints and pops of orange play off one another so well. I'd be tempted to swap bags halfway through the day just because.

The medium Box-Trot would allow me to stash a few extra things when I'm out from morning until night, such as sunglasses, makeup, and even a camera (because again, I will be documenting every detail of this trip). The orange color stands out, yet it's surprisingly wearable. I'd style it with neutrals to give it a solo moment, but pairing it with other orange details like these shoes and the stripe on the pants feels a bit more festive.

Between the shearling vest and the oversize knit, this look has "cozy" written all over it. I love the addition of the crisp, white cotton trousers and baseball cap for a daytime outfit. Come evening, I'd lose the hat, vest, and sneakers in exchange for a blazer and heels. The bag stays because that's the beauty of the Box-Trot—it's casual enough for the daytime and sleek enough for whatever the night brings.

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Photographer: Jared Kocka