How to Travel the World in Chic and Comfortable Style

We all know how stressful packing can be. And how hard it is to look polished and presentable when you’re at the airport and on the plane. While we can’t help you with every element of your packing decisions (although we do have some thoughts on the luggage you should carry), we can help you think about what to wear when traveling by air for business or for vacation. Here are 7 tips on how to travel the world in chic and comfortable style.

how to travel in chic and comfortable style

Between the hassles of packing, getting through the airport, flying and jet lag, traveling is challenging enough without worrying about looking fashionable while we’re doing it. The best rule of thumb seems to be an ensemble that’s easy to get through security with, comfortable on the journey, and sufficiently hardy to keep you looking fresh through disembarkation.

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After years of travelling for both business and pleasure, we’ve developed a couple of tried-and-true “uniforms” for looking sophisticated yet feeling comfortable while on the road. Thanks in part to the rise of increasingly fashionable athleisure, it’s becoming really easy to travel light and look good.

Road-tested tips (and brand picks) for chic travel attire:

1. A Not-So-Basic Tee

You want one that’s soft, not too clingy and made of a silk blend. Though it seems light and airy, silk is actually a warmer material than cotton, making it the perfect choice for chilly air travel. We all know that pure silk wrinkles easily. So, if possible avoid a 100% silk shirt and look something that is made of a blended silk, which won’t wrinkle as easily, keeping you looking crisp and fresh throughout the duration of your trip.

Also when possible, we avoid traveling in white. Stains and spills happen, particularly if you are travelling with young children (we once had a flight attendant spill coffee all over us, and ever since we keep the white jeans in our suitcase).

One of our favorite tops is the F.WORDS Frolic T-Shirt ($98), with its high neckline, soft feel and breezy fit. Rag & Bone has cool-girl tees that pair perfectly with a leather bomber and distressed jeans. Vince has a great line of wool T-shirts in a wide array of colors that are great layering pieces – the hand is super-soft and the fit is very flattering. And we love Ted Baker tees, which are longer and more fitted than many other brands, have a great hand-feel, and come in cheeky British prints that elevate your mood even when the thrill of the journey is flagging.

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2. Technical Trousers

Look for denim with a bit of stretch, tailored joggers or a quality pair of black leggings. You want to be able to move through the airport and curl up to sleep when the time comes.

Lots of people travel in shorts, but we never do because we get too cold on the plane. And the “mom” sweats are just not the look we’re going for here. The trick is finding that precise balance of comfort and chic.

One brand we love that totally goes the distance is F.WORDS – their Frisky Leggings ($300) are hands-down the consummate travel pant (frankly, the everything pant) of choice.  Not only do they provide excellent coverage (meaning no muffin tops), they have thigh pockets that are perfect for storing your phone or even your passport while you are on the go through the airport.

You could of, course level up and spring for a pair of Alaia leggings ($910). But why? We love Theory’s leggings; AG Jeans; Everlane’s Work Pant; and Derek Lam 10 Crosby’s black leggings. The upside of all of these? You can easily re-purpose them for ongoing use throughout your trip, dressing them up or down as needed, which means packing a much lighter bag. Yay!

3. Versatile Layers on Top 

A good coat/sweater/blazer can make an outfit and pull your travel look together perfectly.  Also, when flying you’ll probably want something that will keep you warm in case the plane is chilly (for us, the plane always feels chilly at the start, then feels too hot, so layers are essential – but maybe that’s just us).

Your best bet is to invest in quality pieces in neutral colors that are also multipurpose. One option is a wonderful athleisure coat like the F.WORDS Formation Jacket ($1,350) – it features great tailoring, lots of pocket space (3 large ones, in fact), side vents for regulating temps, easy tech fabric that prevents wrinkling and that are machine washable and lastly, is water and wind repellent. Plus, they’re unisex, so you can trade off pieces with your traveling companions.

Or you could for a lightweight leather jacket from Vince.

For traveling tops, we also love Rebecca Taylor and Trovata shirts, Lingua Franca sweaters and anything from Alice & Olivia by Stacey Bendet – they fit perfectly, wear well, don’t pill, and are fun and happy. Some of them might even start a conversation (most have statements or appliques that will generate a chat while you wait for takeoff).

4. A Relaxed Dress

We’ve seen more and more chic travelers opt for dresses, which can be totally fresh and lovely. A shirt dress, shift or midi dress worn with hard soled shoes or crisp white sneakers and cool sunnies is an excellent look, even if you’re on a business trip. It feels carefree but controlled, and we love it.

Check out day dresses from contemporary brands like Joie and R13.

5. Smart Shorts

We also saw a standout look on a recent trip to Bermuda: a young woman wearing a tailored blue pin-striped shorts suit with sneakers. Hair up, cool sunglasses – she made it look effortless, and that outfit would take you anywhere.

Everlane has terrific shorts in twill and denim; if you want to go high-end, start your beach vacation early by sporting a pair of tough-luxe shorts from Saint Laurent.

6. Cool Shoes 

No frumpy sneakers need apply here, even if the Dad shoe is on trend right now. We are talking about smart statement sneakers, cute slip-ons or flats. (We don’t do sandal or flip-flops because we want a layer between us and the possibly dirty floor at the security check-point, but again, that’s just us).

Whatever you choose, just be sure to pick footwear that’s easy to put on and take off.  You don’t want to be That Person who holds everyone up in the security line with gladiator sandals with strap after strap that just won’t come off.

Keep things simple with a chic pair of sneakers from brands like Golden Goose Deluxe, Gucci, or Louboutin. Or a chic pair of Chanel ballet flats.

7. Simple Hair

Bed-head is not a great look when you’re on the road – it never looks deliberate, even if it is. We love a relaxed ‘do, natural curls, a pony, or even a small chic hat.

If you feel you need a little bit more polish, go ahead and toss on an accessory or two.  Everyone loves a good statement necklace or a great tote bag, and we all know that scarves and wraps can be a life-saver on a long haul flight.

the first rule of travel

Just don’t forget the First Rule of Travel: if you really, really love it, leave it at home. Things go missing and it’s just not worth the risk of heartbreak if something treasured or irreplaceable gets lost or stolen.

There you have it! A few simple tips that will help you move through the world with ease and style. Have a great trip.

join our community

For access to insider ideas and information on the world of luxury, sign up for our Dandelion Chandelier newsletter here. And see luxury in a new light.