I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me

As a semi-recent Los Angeles transplant, I've made so many travel plans over the past two years to take advantage of my new West Coast life, whether it's an international flight to Tokyo or multiday road trip to Sea Ranch, just north of San Francisco. And when I was living in New York City, a quick four-day trip across the Atlantic to London or Paris felt like a breeze. Then there are the long-haul flights I've done from L.A. to Monte Carlo and from Orlando to Hong Kong that take up to a full day of travel. And I've done all this with just a carry-on, mind you, so it's safe to say that I'm kind of a travel and packing expert. This is why I rounded up 20 of the best travel outfits if you're sitting on a plane, in a car, or walking 10 miles in a day to explore your vacation destination.

In theory, your vacations are filled with a never-ending supply of chic new outfits that are more than deserving of a few Instagrams, but the reality is that your travel outfits need to be equal parts stylish and comfortable. Yes, achieving that balance is possible, and we have the stylish looks of the below fashion girls to prove that looking good and dressing functionally can coexist.

From roomy jeans and breezy dresses to versatile boots and bold sneakers that can withstand any mileage, scroll down for 20 travel outfits you'll want to copy for upcoming out-of-office dates.

Breezy Pants + White Button-Down

Don't deny yourself roomy silhouettes! This is the kind of outfit that can take you off the plane and straight to lunch if you don't have time to decompress and change outfits at your hotel.

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Cutout Dress + Sandals + Net Bag

If it's more of a beach vacation, you definitely want to travel with some comfortable sandals and a larger tote that can fit all your beach-day belongings. I find that these net bags fold very flat in a suitcase, but they can fit a seemingly endless amount.

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Jacket + Plaid Skirt + Sneakers

Going somewhere with pretty mild weather? Opt for plaid skirt and sneakers. You can add a bomber in this rich brown shade if the temperature fluctuates.

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Jacket + Bold Sneakers + Comfy Pants

Comfortable pants and shoes are key whether you're on a plane or walking 10,000+ steps, but they don't have to feel drab. Add pops of color with your accessories.

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Matching Sweatsuit + Sneakers

A matching sweatsuit is a must in any wardrobe. With a fashionable pair of sneakers, you can wear it both on and off the plane.

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Quarter-Zip Sweater + Long Coat

Bundle up in a monochrome 'fit like this cream quarter-zip and coordinating coat. Finish it off by adding bottoms with stretch and a trusty pair of shoes.

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Bomber Jacket + Jeans + Shoulder Bag

For a day in a new city where you're constantly moving, it's best to stick to the basics like a roomy shoulder bag, your go-to pair of jeans, and a zip-up jacket for transitional temps.

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Leggings + Oversize Sweater

There's something about gray that makes any outfit look so much more comfortable. Throw on a cream sweater with your gray leggings for some contrast. Then put on your headphones so no one bothers you while you're waiting to board.

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Track Pants + Statement Coat + Flats

Track pants are a staple that can look dressy given the right styling. Take a cue from Helena and add the one statement coat you packed this trip to a pair of sporty bottoms.

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Jumpsuit + Big Tote 

A one-and-done kind of outfit is ideal for travel. When you have a jam-packed day that starts when the sun rises, you don't want to waste any time picking out what to wear. This is where a jumpsuit or boilersuit comes in handy.

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Midi Skirt + Crossbody Bag + Sweater

A crossbody you can keep close to you will ensure your belongings are secure on public transportation. An A-line skirt, a sweater, and statement kicks complete the look.

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Flowy Top + Wide-Leg Jeans + Flats

I tend to turn to less-fitted silhouettes on vacay to keep things easy and effortless. A flowy top and wide-leg jeans are just the solution.

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Maxi Skirt + Knit Polo

For an ensemble that looks pulled together but actually takes five minutes to put on, a knit polo and maxi skirt are all you need. Add your crossbody or top-handle bag to really level things up.

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Quilted Coat + Shoulder Bag + Chunky Sneakers

A coat that doubles as a blanket and/or a pillow on the plane and one you can wear on the daily is a great travel piece if you're heading somewhere chilly. Pack a pair of chunky dad sneakers and a shoulder bag, and you're ready for a day of exploring.

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Knit Sweater + Jeans + Bold Accessories

A cozy sweater, straight-leg jeans, and red accessories are an outfit formula you'll want to remember. And definitely make sure to stop by a café while you're out to fuel up before you hit the pavement again.

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Wrap Coat + Comfortable Boots

Rainy weather won't get you down if you have a fab coat to stay dry in. A trench or raincoat is a must if it's a rainy forecast during your travels, but you can liven it up with bright footwear.

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Coat + Sneakers + Baggy Jeans 

Layer up with a scarf and beanie if your long coat isn't enough to keep you warm. Layering pieces that can go with several outfits are always great to pack, and as someone who lives in sunny Los Angeles, I now relish the trips where I can finally pack my versatile winter clothes.

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Track Jacket + Comfy Jeans

I've worn Adidas shorts on so many trips now, and I've found that sporty pieces are the best to pack. They are durable, made to withstand the elements, and come in handy when you start sweating from all those steps you're getting in. A track jacket is a great piece to wear over a T-shirt or tank. Simply add some fun jeans and a colorful bag, and you'll feel like a street style star wherever you are.

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White Blouse + Black Maxi + Sneakers

A sheer white top is a godsend for those extremely hot travel days. Also, I've worn this black cotton maxi skirt on countless trips. It's one of the best travel items I own thanks to the breezy fit and elastic waist.

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Coat + White Tee + Jeans

Ogling this Rimowa suitcase situation. But a shaggy jacket and unique jeans will dress up any white tee.

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This story was originally published at an earlier date and has since been updated.