Best Madewell Clothing Items for Your Next Vacation
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Planning for your next vacation? You’ll need outfits that keep you comfortable, stylish, and ready to explore. That’s where Madewell comes in. Known for their timeless essentials and travel-ready pieces, Madewell offers everything from breezy dresses to versatile outerwear that can take you from a morning market stroll to an elegant dinner by the sea. As someone who’s spent too much time hunting for the “right” travel clothes, I’ve found Madewell to be a one-stop shop for all my vacation needs. Below, I’ve curated some of their best pieces to pack for your next trip—so you can focus on adventure instead of stressing over your wardrobe.
Whether you’re jet-setting across continents or enjoying a cozy cabin weekend, these Madewell clothing items will ensure you travel in both comfort and style. I’ve reviewed some of their standout pieces, giving you a glimpse of why they belong in your suitcase.
The Perfect Pair of Jeans for Any Destination
The Perfect Vintage Wide-Leg Jean
When it comes to versatile vacation outfits, a good pair of jeans can make all the difference, and The Perfect Vintage Wide-Leg Jean from Madewell lives up to its name. These high-rise, wide-leg jeans are not only stylish but comfortable enough to wear for hours. Whether you’re sightseeing, grabbing lunch at a café, or heading out for the evening, these jeans transition effortlessly from casual to chic. They’re made from Madewell’s signature stretch denim, so you won’t feel restricted even on a long-haul flight or a full day of activities. Pair these jeans with a tucked-in tank top during the day and throw on a light cardigan for cooler evenings—it’s the ultimate vacation outfit hack!
A Relaxed Shirt That Goes with Everything
The Signature Poplin Shirt
A lightweight, breathable shirt is essential for any vacation, and The Signature Poplin Oversized Shirt checks all the boxes. It’s made from crisp cotton, giving it that effortlessly put-together look, even if you’ve just pulled it out of your suitcase. What I love most is how easy it is to dress this shirt up or down—pair it with denim shorts for a casual beach day or tuck it into a skirt for a more polished look.
This shirt also works wonders as a layering piece—throw it over a swimsuit for a poolside lunch, or wear it under a sweater when the weather turns cool. Plus, it comes in several colors, so you can choose a neutral or go bold, depending on your vacation vibe.
Your New Favorite Travel-Friendly Dress
The Satin Button-Front Midi Shirtdress
No vacation wardrobe is complete without a dress that can go from day to night, and the Satin Button-Front Midi Shirtdress does just that. It’s soft, lightweight, and skims the body in all the right ways, making it a flattering choice for warm-weather destinations. I like how this dress feels both elegant and comfortable—it’s perfect for a sunset dinner, but I’ve also worn it with sneakers and a denim jacket for daytime exploring.
The satin material adds just the right amount of sheen, making it look elevated without being fussy. The best part? It hardly takes up any space in your suitcase, so you’ll have room for all your souvenirs.
A Cozy Layer for Cool Evenings
The Kent Cardigan Sweater
Even if you’re heading to a tropical location, it’s smart to bring a cozy layer for cooler nights or chilly flights. Cashmere Button-Front Cardigan Sweater is a perfect travel companion—it’s lightweight enough to pack easily, but warm enough to keep you comfortable on brisk evenings. I love the relaxed sized fit of this sweater; it makes me feel like I’m wrapped in a blanket but still looks effortlessly stylish.
Wear it over a dress or jeans and a t-shirt, and you’re good to go. This cardigan comes in earthy colors that complement almost any outfit, making it one of those pieces you’ll reach for again and again throughout your trip.
Versatile Footwear You Can Walk in All Day
The Kickoff Trainer
Comfortable shoes are a non-negotiable for travel, and the Kickoff Trainer Sneakers from Madewell hits the sweet spot between style and function. These retro-inspired sneakers are cushioned, lightweight, and breathable—ideal for long days spent on your feet. Whether you’re walking through cobblestone streets or rushing through the airport, these trainers will keep you comfortable without sacrificing style.
I’ve worn these with everything from jeans and t-shirts to dresses, and they never look out of place. They’re also easy to slip on and off, which makes airport security a breeze—because let’s be honest, no one wants to be that person holding up the line.
A Bag That Holds It All Without the Bulk
The Transport Tote
Every traveler needs a reliable carry-all, and The Transport Tote is as good as it gets. It’s spacious enough to hold all your essentials (and then some) without feeling too bulky. I love that it’s made from durable leather—it only gets better with age and can handle the wear and tear of travel.
This tote is great for carrying everything from a water bottle and snacks to your camera and sunscreen. It also fits comfortably under an airplane seat, making it an excellent personal item for flights. With the Transport Tote, you’ll have all your essentials at your fingertips without sacrificing style.
Wrapping Up Your Vacation Wardrobe
Packing the right clothes can make your vacation so much smoother, and Madewell offers the perfect mix of comfort, style, and versatility. From the Perfect Vintage Wide-Leg Jean to the Transport Tote, these pieces will take you from the airport to your destination with ease.
And don’t stop here! Madewell has so much more to explore. If you’re looking for even more vacation essentials, check out their denim collection, swimwear, outerwear, and accessories. No matter where you’re headed, Madewell has everything you need to look and feel your best on your next adventure. Safe travels!