Whether you’re dressing up or down, there are those who prioritize comfort and those who don’t. (No judgement: Even the world's best-dressed traveler Victoria Beckham gave up her heels!) But when it comes to travel, the key is to curate a mix of comfy, easy-to-wear wardrobe staples that look all dressed up despite their packing practicality. For your next trip, consider these awesomely functional pieces — all of which work for an Instagram-ready day or night on the town, despite feeling like pajamas. That's what we call winning at life, folks!
1. Short Dress: Boatneck Open Back Dress
Showing off your legs can be sweet and simple in this Kaarem boatneck dress. The flowing silhouette will make it feel like you’re wearing an oversized T-shirt while the open back with the button closure will accent the quality detailing in the piece when you decide to dress it up.
2. Midi Dress: Lemon Leanne Dress
Shhh, don’t tell anyone how comfy the Lemon Leanne Dress by Stella McCartney is. With pleated shiny polyester and a recognizable high-fashion design, this dress looks the part of a fancy dress, but feels like an airy summer midi dress. When this piece isn’t on dinner duty, pair it with relaxed sandals and earthy accessories — like wooden jewelry — to play down the shimmering fabric.
3. Maxi Dress: Belted Chiffon Maxi Dress
What’s not to love about a maxi dress that can fit in on the beach just as well as at a film premiere? The Belted Chiffon Maxi Dress by Kate Spade has a few ultra-flexible factors working in its favor: It’s black, it’s chiffon, it has a gold zipper down the back, and it’s accessorized by a gold belt around the waist. Dressing up a piece like this is simple: Just add heels, a nice clutch, a touch of gold jewelry, and an up-do. Et voila!
4. Skirt: Allen Linen Chambray Skirt
The great thing about chambray these days is that it can be dressed up and dressed down — and unless you’re talking about a to-the-nines event, it works wonderfully both ways. The Allen Linen Chambray Skirt from Bridge & Burn is lightweight and comfortable with an elastic tie waistband. It’s one of those pieces that’s perfect for sandals and a T-shirt, but works just as well with a nice pair of tights and pumps on the bottom and delicately textured blouse. Yay for smooth transitions!
5. One piece: Dressy Romper
Everyone knows that most rompers essentially feel like loungewear, so a romper that can be legitimately dressed up is a traveler’s dream. Pack it for your trip and you’ll have something to chill in and something to network in. This black romper from Flynn Skye has wide legs, an elastic waistband, and pockets. The rayon keeps it soft but the cut makes it absolutely workable for scaling up with the help of the right accessories.
6. Pants: The Street Fleece Pant
These Everlane pants are just super cozy joggers when you get right down to it, but they have zippered pockets and a zipper and button closure, which can give them the illusion of business brunch-worthy pants if you complement them correctly. Pair them with some pumps, a silk shirt, and some statement jewelry — and no one will be the wiser.
7. Jeans: High-Waisted Skinny Jeans
Things seem to be increasingly less formal these days. Some of the priciest restaurants out there are known, in part, for their relaxed atmosphere and casual dress code. While some events remain exclusively black tie, dressing just right for those in-between dress-up events can be tricky. A good pair of jeans can work as your transition piece here, but not just any jeans. You’re unlikely to be able to dress up a classic denim blue shade enough to blur the lines, but a high-waisted black jean like these from DSTLD can do the trick. Since they’re stretchy, they’ll comfortably fit like a glove. Combine with stilettos, a nice blouse, a blazer, and fine jewelry for the ultimate medium dress-up look.
8. T-Shirt: Essential Knit Tee
A cozy T-shirt that can actually work as a part of a dressy ensemble? Sign us up! The Essential Knit Tee from Juicy Couture is the multifaceted tee you’ve been wanting. With sleeves that are a bit longer than traditional, and a soft rayon material, this top is effortlessly comfortable. The sheer yoke panel with a button closure in the back is what takes this one up a notch, and the colors available (vanilla, pitch black, and dragonfruit) are all suitable for dressy pairings.
9. Blouse: V-Neck Long Sleeve Silk Top
This Cos number is the kind of perfect top people mean when they breezily say, “Just pair it with a silk top.” It’s chic, stylish, and will stay in your wardrobe until it wears out (because it’s a timeless piece!). Pull it on over your head and feel the soft silk brush against your skin without needing to worry about clasps or tight fits. You’ll feel like you’re wearing a luxurious pajama set — but from the outside, you’ll look unquestionably dolled up.
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