Ridiculously Comfortable Travel Clothing and Shoes That Don’t Sacrifice Style

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When it comes to travel clothes, you have to choose: comfortable (but looking like you’re setting out on an expedition) or stylish (but uncomfortable for long flights or walking).

However, if you dig hard enough, you’ll find some gems that hit the travel trifecta: comfortable, stylish, and versatile. We’ve done the research for you and uncovered ridiculously soft and good-looking items that will make even the most cramped flight more enjoyable. 

Vineyard Vines Double Brushed Dreamcloth Leggings

We’re officially obsessed with Vineyard Vines’ Dreamcloth fabric, especially in leggings. This buttery-soft material is brushed on both sides for unbeatable coziness, offering a cashmere-like feel inside and out—but it’s much more durable than cashmere. 

The leggings are thick and have a slim cut, so they look more like pants than typical leggings. That means you’ll stay comfortable while still looking polished and put-together.

Neems Custom Jeans

We would never have put jeans anywhere near a list of the most comfortable travel clothing, but then we met Neems. This Los Angeles-based company makes custom jeans tailored to your body to fit like a glove, so you’ll be as comfortable as if you were wearing sweatpants.

You can customize your jeans’ style, wash, stretch, rise, and length to suit your style perfectly. Use Neems’ mobile body scanner app to get your measurements, and the team will craft your denim for you. If your jeans aren’t exactly perfect, Neems will alter and remake them until they get them just right. 

State Cashmere Ribbed Cashmere Pants

State Cashmere’s Ribbed Cashmere Pants are the first-class version of sweatpants. Made from 100 percent Inner Mongolian cashmere (the softest we’ve ever felt), they have an adjustable drawstring waist that’s comfortable no matter how long you’re stuck sitting on a plane. Thanks to the cashmere fabric and ribbed design, the pants have an elevated look, so you can wear them for everything from cozy nights in to casual chic city outfits. 

Billy Reid Cashmere Reversible V-Neck Sweater

For a truly luxurious travel outfit, look no further than Billy Reid. This elegant clothing company specializes in high-quality fabrics and classic designs, both of which you’ll find in its Cashmere Reversible V-Neck Sweater. 

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The tunic-length sweater can be worn with the deep V in the front or back, making it versatile for travel. The double rib detail and cuffed sleeves and hem elevate the sweater to be more than just a basic staple. Made from 100 percent cashmere, it is temperature-regulating, cozy, and ultra-soft. 

Sorel Go Stumptown Bootie 

Sorel’s Go Stumptown Booties are slippers designed for outdoor use. They offer all the comfort of slippers but the benefits of booties. A rubber outsole provides traction and durability in wet or snowy conditions, while the faux fur lining keeps feet warm and comfortable. The booties slip on and off easily, making them a great choice for wearing through airport security on winter trips. 

PrAna Cades Cove Sweater

If cashmere isn’t in the budget, another ridiculously comfortable fabric for travel is Merino Wool. We love PrAna’s Cades Cove Sweater, which is made from a blend of Merino Wool, recycled nylon, and recycled polyester to create the perfect combination of warmth and stretch. 

The sweater’s waffle knit pattern, rolled neck, and slightly cropped style make it comfortable and stylish. 

Backcountry Destination Legging

If you want to hit the ground running at your destination, Backcountry’s Destination Leggings are a great choice. These comfortable leggings are made for everything from long travel days to intense workouts. A UPF 50+ fabric protects your skin from the sun while still being durable, flexible, and moisture-wicking.

The perfectly placed side pocket can fit any smartphone, keeping it easily accessible.  

Barefoot Dreams CozyChic Lite Heathered Travel Shawl

Barefoot Dreams has earned a reputation for its notoriously comfortable fabric. Check it out in the CozyChic Lite Travel Shawl, which is the perfect emergency layer to pack for chilly plane rides. It has two hand pockets that you can use to warm up your hands or to stash a phone or other essentials you want to keep close by. 

India Blake Long Coverup Dress

Comfort is just as important on hot weather trips. Pack India Blake’s Long Coverup dress for beach destinations. Made from 100 percent Tencel Lyocell, the dress is cooling and moisture-wicking. The full wrap skirt, angled hemline, and waist tie belt mean it can be worn as a cover-up or on its own as a dress.

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