Home for the holidays might call for a seasonal stay with family or friends. Whether you’re headed to your final destination on planes, trains, or automobiles, stylish comfort is a must! So today, I’m sharing the perfect What to Wear Where: Holiday Travel uniform that delivers ultimate comfort without compromising style!

Is there anything better than waking up Christmas morning wrapped in a pair of cozy pajamas and adorned in holiday style? If you missed last week’s W2WW, I rounded up What to Wear Where: Christmas Morning looks that do not disappoint! With timeless style, these sets will not only get pulled out year after year but are sure to spark a holiday smile. 

What to Wear Where: Holiday Travel

What to Wear Where: Holiday Travel
What to Wear Where: Holiday Travel-sweatsuit

While you might be looking forward to your next holiday getaway…let’s face it, travel days can be long and even filled with unexpected delays, so comfort is key. I’m setting you up with an effortless travel look that aims for comfy and casual while striking just the right balance between cozy and chic!

This Letter Patch Sweat Set from United Monograms is perfect for holiday travel and can be worn all year long! It offers a cozy, put-together look when the only item on your to-do list is lounging. For added style, choose two monogrammed letters for both the top & bottom to create the perfect personalized matching set! With three color options to choose from, and an added discount with my code at checkout (AMANDA10), this sweat set is an easy pick.

For size reference, I normally wear an xs but opted for a medium in the top, for an oversized, cozy feel. The bottoms do run on the bigger side and I’m wearing a size small.

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Warmest Puffer Coat

puffer coat

Winter temps are here, but this Duvet Puffer Jacket is sure to keep you toasty warm while also looking perfectly polished, no matter where your travel plans take you. Its soft taffeta lining and water-resistant quilted design create a cozy layer you won’t want to take off. The full-length front zipper provides extra room for layering, while the side pockets offer quick access to essentials. This piece is the perfect blend of function and fashion! I’m wearing an xs, and it fits true to size.

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Cozy Footwear

What to Wear Where: Holiday Travel-boots

I’m adding warm and cozy vibes to this What to Wear Where: Holiday Travel look! The Ultra Mini Boot by UGG is considered trendy casual fashion footwear. While it might not be fresh off the runways, it is a well-loved miniature version of the original cult classic.

These boots were definitely made for walking and are oh-so-cozy! The genuine suede upper gives this boot a polished look, while the extra inch of platform offers an ever-so-subtle height boost. Its shearling inner is what dreams are truly made of, creating a cloud-like experience your feet will thank you for. Whether styled with a sweatshirt and denim or a slouchy top and leggings, these boots will keep your toes warm and stylish! This shoe is only available in whole sizes, so size down if you’re in between sizes. These fit tts. 

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Stylish Beanie


I’m adding a touch of luxury to this travel look with a soft Cashmere Slouchy Knit Beanie Hat. It offers a standout style moment with its removable pompom but still serves as functional winter gear, keeping you extra warm. With endless color options, amazing quality, and an affordable price point, you’ll definitely want to add this must-have accessory to your winter wardrobe.

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Luxurious Luggage

What to Wear Where: Holiday Travel-luggage

Your holiday travel look wouldn’t be complete without stylish luggage, and the DELSEY Paris Chatelet Hardside Large Checked Spinner Suitcase does not disappoint! I absolutely love its classic elegant look. Beyond the high-end visual appeal, with leather-like accents, the overall quality of this piece is amazing. The overall design was incredibly well thought out, from the impact-resistant exterior and wheel braking system to its deluxe interior. When scuffs happen, simply buff out with a magic eraser to keep it looking like new. This bag comes in a variety of sizes. I have both the large 28″ and 21″ carry-on. 

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What to Wear Where: Holiday Travel

This casually cozy What to Wear Where: Holiday Travel look is sure to have you headed to your next destination in style!

What’s your favorite piece? Let me know in the comments below!

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XO Amanda

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