37 Travel-Friendly Outfit Ideas For This Season

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It’s the time of year where road-tripping becomes not just a fun vacation idea, but the norm. Many of us are driving (or flying, or bussing, or training) home for Christmas – and that’s a beautiful thing! ‘Tis the season to see friends and family you haven’t for months – or even years.

Luckily for you, we’ve got your back. From the deep archives of Amazon, we’ve rounded up thirty-seven of the coziest, comfiest, and travel-friendly outfits for the holiday season! And if you still aren’t sold? Well, we’ve also made sure each item is inundated with positive reviews and 5-star ratings, so you can be totally sure of high-quality and second to none style…

We hope you find these products as awesome as we do. Just an FYI: We are a participant in the Amazon affiliate program and we may have additional affiliate relationships with some of the products featured here – as such, our company may receive a share of sales from links on this page. Prices on Amazon fluctuate so anything mentioned below might change as soon we publish it!

These Leggings Come in a Cute Capri Length

If you just aren’t sure what the weather’s going to give you, a Capri legging is versatile and comfy in many climates!

The reviews say: “These are definitely my new favorite leggings, I own them in 4 colors and plan to buy more. The colors of the actual leggings are just as bold and vibrant as the photos which I love!”

This Belt is Stunningly Versatile

A good quality belt can take a mediocre outfit to the next level – and this one is a total bargain!

The reviews say: “I was more than pleasantly surprised at the quality and workmanship in this belt. The color was exactly as portrayed on Amazon.
The size was perfect as advertised. I will buy one or two more belts from this supplier. I will recommend it to all my friends.”

This Umbrella Will Have You Covered

You always forget you need an umbrella until it starts raining. Stay prepared with this highly-rated option.

The reviews say: “It secures easily to my laptop bag with a carabiner, and is small and compact, yet fairly sturdy. I don’t know if I would call it windproof, but it’s pretty good – if it’s windy in the city I still need to be careful it doesn’t invert on me.”

These Flared Leggings are Comfy and Stylish

A flared legging offers all the comfort of sweats but looks way more put together!

The reviews say: “I’m absolutely in love with these pants! After I received my first pair, I immediately purchased 2 more in different prints and will purchase more.”

These Socks are Soft Yet Grippy

A comfy pair of socks will take you anywhere – which is handy if you’re traveling!

The reviews say: “I love the way these fit. They are comfortable and give me confidence that I won’t slip. I have a glass chair mat and it’s very slippery. I wear them all day. I like them so much I placed a second order.”

These Leggings are Lined with Fleece

If you’re traveling to a colder climate, keep your legs feeling toasty with these incredible leggings.

The reviews say: “These are like butter for your legs. So soft!”

These Gloves are Amazingly Warm

There’s nothing worse than cold hands on a journey – so make sure to pack these gloves in your carry-on!

The reviews say: “I’ve been trying for years to find gloves that keep my hands warm! No matter how wrapped up I am with layers, if my hands are cold, my whole body is cold. I just received these gloves a couple of days ago and to my surprise, they are extremely warm!”

These Leggings are as Soft as Can Be

You’ve never felt anything quite like these leggings before, and once you’ve tried them, it’s hard to go back!

The reviews say: “The quality of these leggings exceeds the price. I was worried about them being One Size, but they fit me perfectly. All in all, I’d say these are a steal for what you pay and are definitely something I will be getting a lot of use out of.”

This Tie is a Total Bargain!

Make sure you show up in style with this affordable but top-quality tie!

The reviews say: “Out of the dozens of ties that I have accumulated over the years I never had what I considered the perfect black tie. Then I found this one! A quality product from material to craftsmanship to finish. And nice and narrow. The tie I received is perfect in every way.”

These Knee High Socks are Amazingly Comfy

Take your socks up a level (literally) with this slightly longer – but still grippy – pair.

The reviews say: “These almost feel like support socks. This is great as I am working from home and forgot to stand and stretch. The grips are fantastic.”

These Socks are Hugely Festive

Arrive for your holiday travel already in the festive spirit with these cute, patterned socks, which are comfy too!

The reviews say: “These Christmas socks are GREAT! They are just subtle enough that my husband liked them but still Christmas-y. They are very nice quality and color, they are not thin at all.”

This Suit is Perfect for Travel with a Baby

Traveling with a sprog is never the dream – but this comfy suit can help keep them (and therefore, you) happy!

The reviews say: “As soon as it arrived we put it to use. Holy cow, it worked. My son Was waking up 2-4 times at night before wearing the suit. We have used it two nights in a row, and he has only woken up once. I changed him, fed him, burped him, and rocked him and he went right back to sleep in his suit. I am so glad I bought this. It has given me some sleep back.”

These Gloves are Absolutely Adorable!

Ensure you’re never without a pair of gloves by stocking up on this set of cute and cozy options!

The reviews say: “They look well made and soft. They look like the material is a perfect weight. Have not tried them on my grandson but the size looks great. I also like the packaging. We can use it for other items. Nice job!”

These Kids’ Socks have Cute Stripy Options

Offer some perfect travel socks to your pint-sized companion, too, with this grippy and supportive pair.

The reviews say: “These work perfectly. They are soft, fit as expected, go all the way to just above the knee cap, aren’t overly tight at the top (but just tight enough to minimize slipping down), and even have the anti-slip pads on the soles!”

These Gloves can be Used with Touchscreens

There’s nothing more annoying than having to take your gloves off to use a device while traveling. These gloves mean you’ll never need to!

The reviews say: “Bought for my son. Has refused to wear gloves in winter because he can’t use his phone. Problem solved: works great!”

This Headband is a Modern Day Earmuff

Keep your ears warm while on the road with this cute and protective headband.

The reviews say: “Very warm and fit my average-sized head well. Great for hiking during hunting season. I swap into this on winter hikes when my knit hat gets too warm.”

The High Waisted Leggings are Fabulously Flattering

Say goodbye to leggings rolling over at the waistband and falling down. This higher waistband keeps everything in place.

The reviews say: “Overall, these are a great deal. Leggings are my official uniform and great for yoga, too. I will probably be buying another pair.”

These Leggings Have Pockets!

Not enough clothing comes with pockets, and that is a hill we are prepared to die on. But these leggings pass the litmus test!

The reviews say: “Once I tried these leggings on I did not want to take them off, they are so buttery soft it feels like you have nothing on. After wearing all day they were not stretched out and there was no bagging at the knees or anywhere else. I absolutely love these leggings and will be purchasing more.”

These Socks come in an Array of Patterns

Comfy socks are a travel essential – and these sets come with the added benefit of mood-boosting colors and patterns!

The reviews say: “I have bought other socks with cool patterns and the quality varies – some have almost no elastic, others are way too short, others way too thin, and others wear out almost immediately with seams coming undone or elastic breaks. These have none of those problems!”

This Hat is the Ultimate Christmas Accessory

  via Amazon  

Turn up looking like the most festive one of the party in this Santa hat, which comes complete with colorful lights!

The reviews say: “Very good quality and impressive light display.”

These Tights are Perfect for Kids

Keeping your kids comfy is key to a pleasant journey – and these tights manage to be cute at the same time!

The reviews say: “Nice tights perfect for fall they are nice and thick just perfect so my baby girl doesn’t overheat and I can layer her up if it gets colder.”

This Bow Tie Comes in a Huge Shade Range

A bow tie can instantly make any travel outfit feel more formal and festive!

The reviews say: “This was a very well made, nice material tie. It is nothing over the top but it got the job done!”

These Palazzo Pants are Comfy and Stylish

The stretchy material allows for full freedom of movement, while the pattern adds interest to your cozy outfit.

The reviews say: “Love these! I have a bit of a tummy so I love that the band is VERY thick and sucks you in a little.”

These Ear Protectors are a Travel Essential

Travel can be strenuous on your kid’s ears – but these protectors make sure they’re safe and comfortable.

The reviews say: “Look no further. These things are the bomb.”

This Set Spruces up Any Outfit

Adding some braces and a bow tie can make your travel outfit from schlubby to party-ready in seconds!

The reviews say: “High-quality suspenders. The red is a deep red, still a true red but not that bright Christmas red. It is a very pleasing color.”

This Hat is Cute and Cozy

Whoever said that staying warm had to come at the cost of looking absolutely adorable?

The reviews say: “I am so happy with this hat! It is taking all my self-control to not go back and buy all the other colors and generally hate hats – they just never look good on me. Anyway, the inner fleece is microfiber soft and the outer yarn is pretty soft too. If I had paid twice as much, I’d still be happy with this purchase!”

These Socks Offer a Sporty Vibe

Keep your feet cozy and avoid slipping on any surfaces with these cute and comfy socks.

The reviews say: “I actually use these socks to wear with a pair of high heel boots that my feet normally slip around in. These socks do a great job of preventing my feet from slipping around in my boots and they don’t have the extra bulk. They fit like regular socks and my feet don’t feel cramped because of the additional padding. The socks are also a nice modern/athletic style so they don’t look like hospital socks.”

These Socks Keep Your Baby Comfy

Ensure your baby stays happy (and mercifully silent) on longer journeys with these wonderful socks.

The reviews say: “These are perfect and definitely live up to the 5-star reviews! I was having a hard time finding socks for my 2-month-old and with winter coming she definitely needs some good socks. These are not too thick but not super thin. Love the colors (I got the pastel with farm animals) will stay put with all the kicking and squirming.”

These Glasses Protect Your Eyes

We’re all guilty of spending too much time looking at our screens – but these glasses can keep your eyes feeling happy on the go.

The reviews say: “Really love these glasses! The quality is surprisingly beyond the price a lot! My boyfriend thinks it’s really nice on me!”

These Bra Inserts can Keep Your Feeling Modest

Avoid any awkward stares on public transport by slotting these comfy pads into your bra.

The reviews say: “These are very comfortable and easy to wear.”

This Apron is a Christmas Must

Pack this in your travel bag and ensure you don’t let your Christmas dinner ruin any of your outfits!

The reviews say: “I like that the apron has a matte finish and is made with slightly heavy material. The straps are nylon material and are good and strong. The easily adjustable neck loop makes for a great fit.”

This Belly Band Makes Pregnant Travel Easier

Relieve some of the pressure on your bump with this soft yet supportive band.

The reviews say: “After putting this on the first time, I felt relief within 2 minutes. I wear it outside in the heat and it is still very breathable. I also keep it on to sleep.”

These Leggings Come in Tons of Colors

No matter what your travel outfit vibe is, adding in a pair of these leggings will keep you comfy in an array of colors.

The reviews say: “They feel so comfortable you don’t even feel as if you have any pants on! They work wonders with boots and under dresses and long shirts! We love the colors and they hold the colors and size and shape in the wash. They arrived on time and in excellent condition!”

These Gloves Have a Fun Wintry Print

Get truly into the winter spirit with these chunky knit, fair isle print gloves.

The reviews say: “These gloves are soft, warm, and cozy. I ordered the light gray and the color and design are as pictured — medium gray with a white pattern.”

These Socks Have Super Fun Prints

  via Amazon  

Keeping your kid’s socks interesting means you never have to spend hours convincing them to put them on!

The reviews say: “The colors are great. Made well. Standard sizing. Three boys and one girl, ages 7-8. Great stocking stuffers or just as a gift alone. Highly recommend.”

These Socks are Perfect for Ballet Flats

Keep your socks hidden with these foot covers, offering comfort without sacrificing style.

The reviews say: “I purchased this in both beige and black, and I love them! They fit perfectly with my Toms Avalon slip-on.”

These Socks Offer a Cheeky Message

  via Amazon  

Thick comfy socks are perfect for long-haul flights – and these ones also give your travel mate careful instructions.

The reviews say: “The socks themselves are great, very soft and comfortable. I have hardwood and tile floors and these are safer than regular socks to walk around in.