When I’m packing for a trip, Madewell’s clothing racks are pretty much my one-stop shop for creating full travel outfits; everything is comfy, stylish, and high-quality—aka, basically made for museum tours, café-hopping, and everything in between. So when I started prepping for two back-to-back summer vacations to Italy and France, I didn’t even hesitate and went straight to the Soho store in New York City, ready to do some shopping (in the name of research, of course).
If you’re a fellow Madewell fan, I did the hard part for you: I tried on what felt like an entire suitcase’s worth of clothes, and narrowed it down to the styles that looked and felt amazing, and would arrive in good condition after a long flight. As luck would have it, this epic try-on took place during Madewell’s Insider Sale, which is treating Insiders to 30 percent off everything on the site (and what I bought in-store); all you need to do is sign up for a free Insider account to jump in on these exclusive after-summer deals—up to almost 70 percent off.
Three hours, one very patient fitting room attendant, and a lot of mirror selfies later, I landed on 10 travel outfits I truly love. From breezy linen pants and matching sets to flowy maxi skirts and classic summer dresses, there’s something here for every type of trip—and prices start at just $14.
Best Overall Deals
Outfit 1
Travel + Leisure
The moment I slipped into this maxi dress, I knew it was coming with me. The smocked bodice hugs just right without feeling tight, and the gauzy cotton moves beautifully—light and breathable enough for even the stickiest summer days. It’s the kind of piece I can wear straight from a beachside stroll to a sunset dinner.
I styled it with these handwoven ballet flats, which feel surprisingly cushioned for how structured they look. They’re about to sell out, which made buying them an even easier decision. To finish the look, I added a layered shell necklace set for just the right hint of coastal charm. I already have this outfit mentally packed for my wine tour in Tuscany.
Madewell Smocked Maxi Dress
Madewell
Madewell The Mylie Ballet Flat in Handwoven Leather
Madewell
Outfit 2
Travel + Leisure
This pinstriped jumpsuit instantly struck that ideal balance between tailored and easy—the kind of outfit that looks pulled together with zero effort. The wide-leg silhouette adds movement and breathability, and since it’s one piece, it’s a dream for packing light. I paired it with the Milano Mid-heeled Sandals that were shockingly comfortable, even after a few laps around the fitting room.
The now-sold-out Handwoven Shoulder Bag brought texture without the bulk (I was also eyeing the Handwoven Cane Bag, currently $84 for Insiders), and I topped it off with classic aviators for a look that feels just as right for a day of sightseeing as it does for a late-afternoon spritz in Florence. Psst, now’s the perfect time to grab the jumpsuit if you’re an Insider because it’s under $95.
Madewell Pleated Wide-leg Jumpsuit in Pinstripe Linen
Madewell
Madewell The Milano Mid-heeled Sandals
Madewell
Outfit 3
Travel + Leisure
This outfit feels like my ultimate travel uniform—relaxed, versatile, and ready for the heat. The Cotton Double-gauze Oversized Shirt is airy and lightweight, ideal for hot days when I still want to look put together. I styled it with the Relaxed Pleated Trouser Shorts in 100% Linen that drape beautifully and have that easy, effortless vibe I always look for in warm-weather outfits.
The braided belt adds shape, while the strappy toe-ring sandals pull everything together with a low-key, Euro-summer feel. I can already picture myself rewearing this entire look for everything from market mornings in Provence to lazy beachside lunches in Cinque Terre.
Madewell Cotton Double-gauze Oversized Shirt
Madewell
Madewell Relaxed Pleated Trouser Shorts in 100% Linen
Madewell
Outfit 4
Travel + Leisure
I’ve always loved a matching set for travel, and this linen duo is the kind of outfit I’ll reach for on repeat. The curved-hem shorts offer a flattering shape without feeling fussy, and Easy Button-up Shirt has a clean, minimalist cut that makes it feel a little elevated.
Worn together, the set is an easy go-to for mornings when I don’t want to think too hard about what to wear. I also love how versatile it is—I can pair the shorts with a white tank or throw the top over jeans for a totally different look. To finish the outfit, I added these double-strap slingback sandals that feel sporty and polished at once, and just right for any casual day on the go.
Madewell Curved Hem Pull-on Shorts in 100% Linen
Madewell
Madewell Linen Easy Button-up Shirt
Madewell
Outfit 5
Travel + Leisure
This midi skirt is one of those rare finds that call for comfort without compromising on style. The smocked waistband sits comfortably and moves with you, and the blue-jean shade offers a dressier twist on classic denim while still pairing easily with anything in my suitcase. I styled it with Madewell’s ribbed tank, a staple I always pack because it layers well and goes with everything.
I finished the look with The Handwoven Straw Mini Tote, which is spacious enough to hold all the essentials—sunglasses, a Kindle, sunscreen, and even a camera—while still looking pulled together for exploring a new city.
Madewell Smocked-waist Denim Midi Skirt
Madewell
Madewell Regenerative Cotton Ribbed Scoopneck Tank
Madewell
Outfit 6
Travel + Leisure
The Zoe Relaxed Linen Pants will become my go-to for a relaxed travel day look, since they’re so comfortable without feeling lazy. The wide-leg cut is incredibly breezy, and the subtle vertical stripes make it feel just a little more elevated.
I paired the pants with their cotton V-neck tank that’s soft, easy to layer, and one of those pieces I’ll end up reaching for every day of my trip. To tie it all together, I slipped on the Maude double-strap sandals again—they’ve been a surprisingly versatile staple in every outfit I tried.
Madewell The Zoe Relaxed Wide Pant Linen Pants
Madewell
Madewell Slub Relaxed V-neck Tank
Nordstrom Rack
Outfit 7
Travel + Leisure
This outfit feels like summer in a snapshot. The 1997 Denim Bermuda Shorts have a retro-cool vibe but still feel modern with a clean, high-rise fit. I tucked in this Boatneck Bubble Tee, which has a slightly boxy shape that balances the slim shorts perfectly.
Here, the braided belt polishes up the look, while the ankle-wrap leather sandals add a fun, feminine twist that makes the whole outfit feel vacation-ready—whether I’m off to the farmer’s market or grabbing lunch along the coast.
Madewell The 1997 Denim Bermuda Shorts
Madewell
Madewell Boatneck Bubble Tee
Madewell
Outfit 8
Travel + Leisure
The second I put on the Striped V-neck Midi Dress, I felt like I was somewhere in the South of France. It’s made from 100 percent linen, so it’s naturally breezy, but the flattering V-neck and midi length give it a more refined, all-day-wear kind of feel.
My favorite feature is definitely the pockets, as it adds to the carefree travel look. It’s the kind of piece I’d wear to a garden lunch in Provence or throw on after a swim when I still want to look pulled together. I kept it simple with the Logan Aviator Sunglasses—classic and cool, just like the dress.
Madewell Striped V-neck Midi Dress
Madewell
Madewell Logan Aviator Sunglasses
Madewell
Outfit 9
Travel + Leisure
This might be my favorite outfit of the bunch. The Linen Maxi Slip Skirt has such an effortless drape and moves beautifully with every step. I styled it with the Linen Scoopneck Cutaway Vest for a head-to-toe monochrome look that feels modern and put-together without being too precious.
It’s a lightweight, breathable pairing that works just as well for city wandering as it does for a casual dinner out. I finished it with the mini handwoven tote, which fits all the essentials and adds a bit of texture.
Madewell Linen Maxi Slip Skirt
Madewell
Madewell Linen Scoopneck Cutaway Vest
Madewell
Outfit 10
Travel + Leisure
The Poplin Seamed Maxi Dress is a dream for hot, sticky weather—the structured seams give it shape, but the cotton fabric keeps things feeling light and airy. It’s one of those dresses that looks great with minimal effort, which is exactly what I need when I’m living out of a suitcase.
I added the Organic Wide Cuff Bracelet to dress it up a bit, and I love how the contrast makes the outfit feel city-ready without being overdone. I could easily wear this to explore a new neighborhood or grab a last-minute dinner reservation. I also love the pop of color.
Madewell Poplin Seamed Maxi Dress
Madewell
Madewell Organic Wide Cuff Bracelet
Madewell
Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.
