25 Cute and Comfy Travel Outfits

Prepare for your trip with these 25 cute and comfy travel outfits. Pack light by bringing your favorite pair of jeans, but changing them up with an oversized sweater, T-shirt, scarf, and coat. When you are going out at night, you can throw on a blazer and a pair of booties, since heels might kill your feet. Style and comfort can definitely go hand in hand if you have the right basics. It’s all about getting creative and changing up your look to keep your style fresh throughout the trip.

Get all the tips and inspiration in these 25 cute and comfy travel outfits here…

  • 25 Cute and Comfy Travel Outfits 1 of 26
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  • Slouchy 2 of 26
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    Now this outfit definitely takes the cake for most comfortable travel style.
    Find out more at Indulgy.

  • A Blazer for Business Travel 3 of 26
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    Add a blazer to your comfortable sweater and pants outfit for a classy business look.
    Find out more at Lolobu.

  • Going Somewhere Sunny? 4 of 26
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    Taking a vacation somewhere warm? Pack your sandals, oversized t-shirt, and a long-sleeve shirt for the breeze.
    Find out more at Good Bad and Fab.

  • Khakis and a White T 5 of 26
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    A t-shirt and khakis are a great way to stay comfortable when traveling. Throw in a pair of Chuck's for comfort and they're light to pack.
    Find out more at Summer Lee.

  • Comfortable Cargo 6 of 26
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    If you don't like sweats or leggings, a pair of cargo pants are roomy, slightly baggy, and still look adorable.
    Find out more at Frills for Thrills.

  • Jeans and a Sweater 7 of 26
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    A baggy sweater, cute jeans, and your most comfortable boots make a stylish way to see the sights.
    Find out more at Zoronnah.

  • Trench Coat and Jeans 8 of 26
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    A trench coat can be your best friend when you're traveling. Since it's in style, you'll always look fashionable no matter what you have on beneath. 
    Find out more at Marilyn's Closet Blog.

  • Maxi Skirt 9 of 26
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    Wear a flowy maxi skirt that is lightweight with a favorite t-shirt on top.
    Find out more at Mona's Daily Style.

  • Baggy Jeans 10 of 26
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    Baggy jeans are a great, loose, and comfortable addition to your traveling outfit with an oversized blazer to give it style.
    Find out more at Liza Chloe.

  • Go Bold 11 of 26
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    Add style to your favorite jeans and t-shirt with a bold, printed wrap and oversized handbag.
    Find out more at Lolobu.

  • Leggings & Sneakers 12 of 26
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    Leggings will keep you comfortable and relaxed if you have a long road trip ahead of you.
    Find out more at The Muse.

  • Baggy Sweat Pants 13 of 26
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    These oversized sweat pants still look stylish with a cropped top and clutch.
    Find out more at Fashion Finder.

  • Leggings and Layers 14 of 26
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    Put on a pair of leggings under your oversized sweater with a matching beanie and colored handbag.
    Find out more at Scent of Obsession.

  • Jeans and Uggs 15 of 26
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    Tuck loose jeans into your Uggs with a chic sweater to style it up.
    Find out more at Red Riding Hood.

  • Maxi Skirt and Thermal 16 of 26
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    A thermal top can roll up small in your suitcase and can be worn with jeans or a loose maxi skirt.
    Find out more at Chic Dresses.

  • Leggings, Oversized T-Shirt, and Scarf 17 of 26
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    Add a print to your leggings and oversized t-shirt with a patterned scarf.
    Find out more at 5th and Vine.

  • Slouchy Boots 18 of 26
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    Grab a pair of comfortable slouch boots to add style to a simple outfit. Tuck leg warmers in to keep yourself extra warm. 
    Find out more at Chicisimo.

  • Loose Sweater 19 of 26
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    Choose a loose sweater with a muted color to wear with all your travel outfits.
    Find out more at Back East Blonde.

  • Business Travel 20 of 26
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    If you are doing business while traveling, bring a button-down you can put under a warm sweater. 
    Find out more at  Living Color Print.

  • Add Jewelry 21 of 26
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    One of the easiest ways to feel dressed up when you've been traveling is with a touch of jewelry.
    Find out more at  More Pieces of Me.

  • Flats 22 of 26
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    Pack a pair of patterned flats to slip on when you're heading out for dinner.
    Find out more at 500px.

  • Maxi Dress 23 of 26
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    The maxi dress is a basic you can change up with jewelry and belts throughout your trip.
    Find out more at  Beauty and Bows.

  • Comfy Oversized Sweater and Bling 24 of 26
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    Throw on an oversized sweater, but dress it up one day with bright gold or metallic jewelry.
    Find out more at  Living Color Print.

  • Dressing Up While Traveling 25 of 26
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    Opt out of the tiny heels when you're traveling and dress up with a comfortable pair of booties.
    Find out more at  The Oxford Trunk.

  • PJ Shirt 26 of 26
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    If you're traveling overnight, make your PJ shirt your all day shirt.
    Find out more at Style Worth While.

Jaime Morrison Curtis is author of the bestselling book Prudent Advice: Lessons for My Baby Daughter (A Life List for Every Woman), follow up fill-in journal My Prudent Advice, and founding co-editor at Pretty Prudent, the premier design and lifestyle blog providing inspiration and instruction to help anyone create beautiful things, food, and experiences for their friends and family.

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