I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me (2024)

I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me (1)

(Image credit: @amaka.hamelijnck)

As a semi-recentLos 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 toTokyo or multiday road tripto Sea Ranch, just north of San Francisco. And when I was living in New York City, a quick four-day trip across the Atlantic toLondon orParis felt like a breeze. Then thereare 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 exploreyour vacation destination.

In theory, your vacations are filled witha never-ending supply of chic new outfits that are more than deserving of a few Instagrams, but the reality is that yourtravel outfits need to be equal partsstylishandcomfortable. 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 for20 travel outfits you'll want to copyfor any upcoming out-of-office dates.

Coat + White Tee + Jeans

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(Image credit: @alyssainthecity)

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

Shop the key pieces:

Ena Pelly

April Faux Fur Teddy Jacket

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Levi's

501 '90s Straight Leg Jeans

Jacket + Bold Sneakers + Comfy Pants

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(Image credit: @himichelleli)

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.

Shop the key pieces:

Onitsuka Tiger

Mexico 66

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Osoi

Hobo Brocle Bag

Matching Sweatsuit + Sneakers

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(Image credit: @aimeesong)

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.

Shop the key pieces:

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Reformation

Classic Crew Sweatshirt

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Reformation

Boyfriend Sweatpant

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Donni

Rib Cardi Sweater

Quarter-Zip Sweater + Long Coat

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(Image credit: @piabaroncini)

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.

Shop the key pieces:

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Zara

Soft Hooded Coat

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Varley

Mentone Half Zip Sweater

Bomber Jacket + Jeans + Shoulder Bag

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(Image credit: @alessandragl)

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.

Shop the key pieces:

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Lioness

Bomber Jacket

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Rebecca Minkoff

Darren Signature Carryall Bag

Leggings + Oversize Sweater

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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.

Shop the key pieces:

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Nordstrom

Oversize Wool & Cashmere Sweater

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Skims

Stretch Cotton Rib Leggings

Track Pants + Statement Coat + Flats

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(Image credit: @helenacuesta)

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 with a pair of sporty bottoms.

Shop the key pieces:

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BDG

Melanie Faux Fur Denim Jacket

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Adidas Originals

Relaxed Sweatpants

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Zara

Velvet Ballet Flats

Jumpsuit+ Big Tote

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(Image credit: @dronme)

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.

Shop the key pieces:

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Amo

Skip Jumpsuit

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Mango

Floral Crochet Bag

Midi Skirt + Crossbody Bag + Sweater

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(Image credit: @sofiamcoelho)

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

Shop the key pieces:

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Cos

Ripple Crossbody

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Urban Renewal

Remade Quilted Liner Maxi Skirt

Flowy Top + Wide-Leg Jeans + Flats

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(Image credit: @thatgirlyusra)

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.

Shop the key pieces:

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Levi's

Ribcage Wide Leg Jeans

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Tony Bianco

Miami Black Nappa Flats

Maxi Skirt + Knit Polo

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(Image credit: @livvperez)

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

Shop the key pieces:

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Mango

Long Knitted Skirt

Tory Burch

Petite Lee Radziwell Double Bag

Breezy Pants + White Button-Down

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(Image credit: @elizagracehuber)

Don'tdenyyourself 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.

Shop the key pieces:

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H&M

Oxford Shirt

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Leset

Kyoto Carpenter Pants

Jenny Bird

Florence Earrings

QuiltedCoat + Shoulder Bag + Chunky Sneakers

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(Image credit: @naomigeorgeo)

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.

Shop the key pieces:

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Everlane

The ReNew Long Liner

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New Balance

1906R

Jacket + Plaid Skirt + Sneakers

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(Image credit: @chanelmckinsie)

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

Shop the key pieces:

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Mango

100% Leather Bomber Jacket

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J. Crew

Pleated Skirt

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Adidas

Handball Spezial Shoes

Knit Sweater + Jeans + Bold Accessories

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(Image credit: @maddiebriell)

A cozy sweater, straight-leg jeans, and red accessoriesare an outfit formula you'll want to remember.And definitely make sure tostopby a café while you're out to fuel up before youhit the pavementagain.

Shop the key pieces:

I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me (50)

RE/DONE

Crewneck Cable Pullover

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Mansur Gavriel

Square Toe Ballerina Flat

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Kimchi Blue

Mae Retro Baguette Bag

Wrap Coat + Comfortable Boots

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(Image credit: @spicy.mayo)

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.

Shop the key pieces:

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Good American

Chino Trench Coat

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Sorel

Brex Waterproof Chelsea Boot

Coat + Sneakers + Baggy Jeans

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(Image credit: @amaka.hamelijnck)

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.

Shop the key pieces:

New Balance x Ganni

1906R

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Agolde

Dame High Rise Wide Leg

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Mango

Fringed Edge Scarf

Track Jacket + ComfyJeans

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(Image credit: @anaasaber)

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.

Shop the key pieces:

I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me (61)

Lacoste

Logo Monogram Stripe Track Jacket

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Brandon Blackwood

Mini Duffle Bag

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Diesel

D-Sire Cargo Jeans

White Blouse + Black Maxi + Sneakers

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(Image credit: @ladhav)

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.

Shop the key pieces:

I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me (65)

Doen

The Jane Blouse

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Staud

Sea Skirt

Cutout Dress + Sandals + Net Bag

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(Image credit: @chrissyford)

If it's more of a beach vacation, you definitely want to travelwith 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.

Shop the key pieces:

I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me (68)

SIR.

Lupita Shaped Midi Dress

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Mdouly

Crochet Bag

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Ancient Greek Sandals

Clio Leather Sandals

Explore More:

Style TipsOutfit Inspiration

I Travel 5 Times a Year—These Easy Outfits Have Never Once Failed Me (2024)

FAQs

How do I look good when traveling? ›

However, you can be comfortable yet still stylish by choosing wrinkle-free fabrics, wearing layers, and keeping your skin moisturized. Choose simple but chic makeup and hair for traveling to look your best when you arrive. Take advantage of down time on the plane or in the car to catch up on your rest.

Continue Reading ›
How many days of clothes can you fit in a carry-on? ›

Yes! You can pack 10 days of clothes in one carry-on bag. The key is to pack clothes that all work together, and of course, to use clothing organizers that maximize the space in your bag.

Discover More Details ›
How do you pack for 5 days in a carry-on? ›

Five days is a piece of cake. Use packing cubes, roll your clothes. Shoes, wear your bulkier pair, pack one additional pair and/or water/shower shoes. Pack 2-3 pair of pants, 3-4 shirts, with a sweater and layering piece.

Keep Reading ›
What is the 54321 packing rule? ›

We believe the secret to becoming a light packer is the 54321 method. For a weeklong holiday, that means you'll need: five shirts and/or T-shirts, four pairs of trousers, three accessories (think hats, belts and sunglasses), two pairs of shoes and one pair of swimming trunks.

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What is the 5-4-3-2-1 packing method? ›

Its version of the 5-4-3-2-1 method includes "five tops, four bottoms, three accessories, two shoes (a practical pair and a nice pair), and one swimsuit," though like the Times this formula allows the wiggle room to swap out accessories based on your destination and type of travel.

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How do I look classy on a plane? ›

Designers Share Their Top Long-haul Style Tips
  1. Dress in black and white. “Monochromatic tones are an effortless way to look your best. ...
  2. Choose wrinkle-resistant fabrics. ...
  3. Stick to a uniform. ...
  4. Pack a different outfit for the plane. ...
  5. Dress in cashmere. ...
  6. Carry a stylish bag. ...
  7. Take mini hair products.

See Details ›
Is it OK to wear sandals on an airplane? ›

Comfort and Safety in the Skies

Also, in the unlikely case of emergency situations, sandals offer less protection and grip than closed-toe shoes, raising safety concerns. While it seems like a bad idea to wear flip-flops on a flight, you can always wear them once you have landed and got your carry-on luggage out.

Discover More ›
What are the best clothes to fly in? ›

Regardless of the weather in your final destination, breathable layers — like a cardigan or cover-up — will help you regulate your own body temperature and keep you comfortable throughout the flight. Comfort is another key when considering what to wear on a plane, although you shouldn't turn up in your pajamas.

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What is not allowed to take on an airplane? ›

Firearms, ammunition, and fireworks are prohibited, as are all knives and safety razors (including pocket knives and Swiss Army knives). Straight razors and replacement blades for straight razors are also not allowed. Most tools also cannot be packed in carry-on luggage, as they have the potential to cause harm.

Read More ›
Can you take snacks in your purse on a plane? ›

Solid food items (not liquids or gels) can be transported in either your carry-on or checked baggage. TSA officers may instruct travelers to separate items from carry-on bags such as foods, powders, and any materials that can clutter bags and obstruct clear images on the X-ray machine.

Read The Full Story ›

Is toothpaste considered a liquid on airplanes? ›

Since toothpaste is considered a liquid, paste, or gel by the TSA, most of us toss those tiny one-ounce tubes in our carry-on bags. However, if you want to ditch the hard-to-recycle packaging, consider toothpaste tablets, an ecofriendly alternative that's not subject to the 3-1-1 rule.

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Can I bring toothpaste in my carry on? ›

The answer is yes. Toothpaste is permitted on aircraft but only in quantities of 3.4 oz (100ml) or less. The same goes for lotion, shampoo, shaving cream, etc. If you are only travelling with carry-on baggage, keep in mind all these rules when bringing your liquids through security checkpoints.

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What's the 1 5 rule? ›

The essence of the 1:5 Rule lies in the art of prioritization. It's a conscious decision to turn away from the allure of impulsive shopping sprees, the captivating charm of fast fashion, the indulgence in expensive alcohol, the allure of gourmet food deliveries, and the tantalizing array of beauty products and makeup.

Show Me More ›
How do you pack light for a week in the sun? ›

Holiday checklist items that you should always include:
  1. Shorts.
  2. Sun hat.
  3. Sun dress.
  4. Flip flops.
  5. Beach towels.
  6. Beach bag.
  7. Sun cream.
  8. Swimming costumes.

Keep Reading ›
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