The Art of Stylish, Comfy Travel

By Bobbi Schwartz
December 5, 2022

There’s something to be said for looking chic and being comfortable when traveling.

Knowing how to accomplish both is an art form that can pay off in spades when you learn the formula. Not only will you achieve noticeable comfort, but you will also look fabulous dressed in stunning simplicity.

If you’re traveling anytime soon, implement these style tips for stress-free travel dressing.

The Color Palette

I always encourage an all-black color palette: It’s the best way to hide any spots you might incur in transit. In terms of chic, the visual impact of black is massive, and the ease with which you can pull your look together is tremendous. Travel is stressful enough these days; simplifying what you wear means one less thing to worry about as you plan your trip.

Travel Bottoms

So, what is a winning travel look? Let’s start with my favorite: Leggings, yoga pants, wide-leg pants, and even lightweight joggers. Note: Always wear fresh-looking bottoms when traveling as opposed to the ones you’ve been living in at home. Though the look you’re going for is casual, you want to appear polished.

If you prefer jeans, wear them, but remember you want to be comfortable. Doctors recommend clothing that “gives” to compensate for swelling that occurs when flying. If you wear jeans, select bootcut or flare-leg jeans as they appear more put-together.

Travel Tops

I like longer fluted T-shirts for tops, since the A-line silhouette is flattering on every body shape. Here you will want to go with black or white when choosing colors.

I’m partial to oversized white collared shirts. This look packs a punch when worn with a blazer as your “third piece” — the finishing touch that pulls your look together. These timeless white cotton shirts also look wonderful worn out over cropped leggings.

Black tunic sweaters are another silhouette for your travel wardrobe. They look great over a white T-shirt and can work beautifully as your third piece, worn as a top, or tied around your waist or shoulders. They are easy, flattering, and perfect for layering to accommodate fluctuating in-flight temperatures.

Third Pieces

Cardigans pair easily with T-shirts and will keep you cozy in transit. This year’s double-breasted blazers are popular and fabulous! The double-breasted silhouette is always a showstopper, so that’s what I lean toward when choosing a blazer as a third piece. It truly ups your chic.

A denim jacket worn or tied at the waist is another excellent third-piece option. The contrast of the denim against an all-black color palette really pops your look.

Regardless of the style route you choose, your third piece is the glue that pulls your look together. Always keep this in mind when deciding what to wear.

Travel Accessories

A few fabulous accessories add polish. Consider items such as sunglasses in classic silhouettes and simple choices for jewelry like pearl or diamond studs or small gold or silver hoops. And you’ll want to purchase a cashmere wrap for your travels. I’ve always been partial to Loro Piana wraps; they’re luxurious and cozy! I never leave home without mine.


Comfort is essential, so I primarily go with flats or ankle boots. Of course, in the warmer months, I recommend traveling in a pair of flat sandals.

I don’t want to discount slides and mules as an option, as those styles are also comfy and chic for travel. Pointy-toe ankle booties also look sensationally stylish. And if you decide on booties, they will only work for you when worn with a bootcut, flare-leg, or wide-leg bottom.

As you embark on air travel, be sure to implement these tips for stress-free, chic looks that are oh-so-comfortable wherever your destination is.

Bon voyage!

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