Crafting the perfect travel outfit can be tricky: You want something comfortable but not sloppy and ideally made up of pieces that won’t look so beat-up when you arrive that they’ll be dead in the water for the rest of your trip. I put a lot of thought into every article of my ensemble—even the pieces that might seem like a bad idea at first glance have some logic behind them.
Outfit #1: The Big Boyfriend Jeans
One of my newest favorite jean iterations is the oversize boyfriend jean. It basically sits on the complete opposite end of the spectrum from skinnies and isn’t just slouchy but truly baggy (wearing these in a car or plane is the comfort equivalent of sweats). Counterbalance the aggressive fit with a tighter top, like a peplum blouse. The fit-and-flare waist keeps the outfit from overwhelming your shape. Feminine flats are easy to slip on and off and also keep the pants from reading as too masculine.
Citizens of Humanity jeans
Topshop tank, $56
Aldo flats, $65
Outfit #2: The Maxidress
This no-brainer outfit is one of my go-tos for travel, and, for summer, I love a white dress. Besides the obvious (you can lie down, stand up, or sit cross-legged and still be comfortable), a maxi will come out of the journey without substantial wrinkles or creases, making it ripe for re-wearing. Top it off with a lightweight jacket in case the AC gets cranked up too high—one that’s not too bold so you can wear it multiple times on your trip without being that girl in the pink-and-blue floral bomber. Unless you’re hiking somewhere, most travel involves very little actual time on your feet, so take this opportunity to wear the clunky (but cute!) and heavy platforms that’d take up half your suitcase.
Old Navy dress, $45
7 for All Mankind jacket, $265
Zara wedges, $80
Outfit #3: The Skinny Jeans That Don’t Get Baggy
There’s nothing sillier than packing a pair of jeans that, after one wear, are so stretched out you can’t slip them on again without a full wash-and-dry cycle. Enter Paige Denim’s brand-new Transcend launch, made with a special performance fiber crafted especially to hold fit. Up top, I like to wear a denim button-up that’ll pull double-duty after landing (whether worn open over a tank, knotted with a dress, or as a cover-up over a bikini). Shoe-wise, I apply the same philosophy as the platforms with my maxidresses. I’ll wear the biggest shoe I’m bringing, like these kind of-awesome satin Supergas from the brand’s recent collaboration with the Man Repeller.
Paige Denim jeans, $169
H&M shirt, $25
Superga sneakers, $125