Skip to Content

What to Wear While Traveling for the Holidays

If you have holiday travel plans on the calendar, you’re facing enough stress without having to worry about what to wear while traveling. Once you step out the front door with your bag in hand, your immediate future might involve:

  • Travel delays
  • Familial conflict about politics
  • Someone getting drunk and/or crying
  • Awkward interactions with relatives who are close huggers or close talkers

Sadly, the right sartorial essentials won’t get your plane to land on time or soften the extreme edges of your family circle. But with the right set of travel clothes, you can at least feel comfortable and stylish — no matter what happens. Even if your holiday plans devolve into chaos, you’ll look good enough to snap a few selfies along the way. And that’s important, because when things don’t go according to plan, a selfie gives you an excuse to smile.

This post may contain affiliate links*

You may find yourself walking the city streets, hopping on and off public transport, or having lunch on the boardwalk. And those things are all way more fun when you’re not constantly readjusting your floaty outerwear. Look for something that’s not too bulky, but substantial enough to stay put on a windy day.

WEESO Womens Winter Long Sleeve Sweaters Pullover Tunic Tops for Leggings Blue M
  • 【Stylish Design】Beautiful puffy…
  • 【All Match】This long sleeve…
  • 【Occasions】The trendy puff…
  • 【Size】The tunic top being great…
  • 【Note】It’s easy to care for,…
LILLUSORY Women’s Fall Cardigans Trendy Cable Knit Chunky Duster 2023 Lightweight Oversized Button Sweaters Loose Barefoot Dreams Outwear
  • Material: The cardigan sweater is…
  • Features: v neck, long sleeve, open…
  • Occasions: Suit for casual wear,…
  • Washing: We suggest hand washing…
  • Size recommendation: Please refer…
Bluetime Women Long Sleeve Cable Knit Soft Sweater Oversized Loose V Neck Pullover Tops Casual Plain Tunic Sweater (XL, Khaki)
  • Comfortable Material: The fabric of…
  • Unique Design: Fall pullover…
  • Easy to Match: Oversized sweaters…
  • Suitable Occasion: Great for…
  • Garment Care: Washing by hand…

2. T-shirt

Layering is key to dressing for comfortable travel. The day you dress for a cold airplane is the day the plane will sit on the tarmac without A/C for two hours. Be prepared by wearing a comfortable cotton t-shirt underneath your sweater.

SaleBestseller No. 1
Hanes Women’s Nano T-Shirt, Medium, White
  • QUALITY FABRIC – Hanes Perfect-T…
  • PRE-SHRUNK – Wash and wear this…
  • VERSATILE CREWNECK – Hanes…
  • CONVENIENT TEARAWAY TAGS – Getting…
  • MULTIPLE OPTIONS – The options…
Bestseller No. 2
4 Pack: Womens Cotton Crew Neck Scoop Short Sleeve T-Shirt Women Shirt Tshirt Tshirts Shirts Athletic Tee Tops Casual Blouse Tees Lounge Ladies Basic Workout Classic Relaxed Loose Fit – Set 4,XL
  • The perfect fit: Our Women’s Cotton…
  • Versatile and comfortable: These…
  • Product features: Our Women’s Crew…
  • Affordable and convenient: With a…
  • Real Essentials’ Commitment to the…
Bestseller No. 3
Amazon Essentials Women’s Classic-Fit Short-Sleeve V-Neck T-Shirt, Pack of 2, Charcoal Heather/Light Grey Heather, Large
  • CLASSIC FIT: Close but comfortable…
  • COTTON MODAL BLEND JERSEY: Super…
  • ESSENTIAL T-SHIRT: This versatile…
  • DETAILS: Features a classic v-neck…
Bestseller No. 4
Hanes Standard Originals Oversized T-Shirt, Cotton Crewneck Tee for Women, Plus, Urban Lilac
  • BASICS THAT ARE FAR FROM BASIC – A…
  • SHAPED TO FLATTER – A slightly…
  • COLLECTIBLE COLORS – Priced so you…
  • SOFT COTTON, PURE COMFORT – Soft,…
  • WONDERFULLY ROOMY – Relaxed and…
SaleBestseller No. 5
Hanes womens Nano Premium Cotton V-neck Tee fashion t shirts, Black – 1 Pack, Large US
  • Lightweight 100% ring-spun cotton…
  • Slightly contoured fit with side…
  • Will hold its shape even after…
  • Double-needle sleeve and bottom…
  • Features an easily removed…

3. Pull-on pants or leggings

A comfy pair of stretchy pants can be the MVP of your trip. If they fit right, they won’t bunch or pinch even after hours of sitting in a car or airplane. You can also pack multiple pairs in a small bag and they’re ideal for layering under skirts and dresses on cold days.

If you’re opposed to wearing leggings as pants, try a slim fit jogger. Not as tight on your backside, but just as comfortable.

Sale
Hue Women’s Ultra Soft High Waist Denim Leggings Sockshosiery, -black Indigo Wash, Small
  • STUN IN DENIM: Meet your casual…
  • FOR EVERY TASTE: Our commHUEnity…
  • A FIT THAT FLATTERS: At HUE; we…
  • CREATED TO LAST: No more dealing…
Marika Women’s Eclipse Tummy Control Bootleg Pant, Black, Small
  • High-rise, full length bootleg yoga…
  • Self-side seam pockets allow you to…
  • Made of Stretch Opatek Luxe: The…
  • Reflective logo detail. Focus on…
  • Inseam: 32 inches
Leggings Depot Women’s ActiveFlex Jogger Pants with Pockets (Full Length, Black, Large)
  • Premium Quality Fabric : Our…
  • High Rise Waistband : Our active…
  • Multiple Functional Pockets :…
  • Tapered Leg Design : Offers a sleek…
  • Stylish and Versatile : These…

4. Slouchy beanie

A slouchy knit beanie serves more than one purpose. It keeps your head warm when you’re pumping gas on a cold day, it camouflages greasy roots and bad hair days, and it looks chic in a low-maintenance kind of way.

Opt for a chunky knit and a slouchy style in a neutral color, so you can wear it again and again.

Sale
Somaler Knit Beanie Hat for Women Oversize Chunky Winter Slouchy Beanie Hats Ski Cap Army Green
  • 1) Beanie for women: Our Winter…
  • 2) Slouchy beanie For Women : This…
  • 3) One size fit Most .No matter…
  • 4)Winter hats for women ,our beanie…
  • 5) Womens Stylish beanie : you can…

It’s tough to beat Somaler’s highly rated knit beanie, available on Amazon. Choose from a range of color choices. You can also snag a two-pack at a discount or a beanie-and-infiniti-scarf set.

5. Booties

Tall, clunky boots are tough to transport, especially if you don’t want to wear them en route to your destination. Booties make a sensible alternative because they’re more comfortable and easier to pack. With some creativity, you could even jam them inside a carry-on.

Consider a weatherproof model if you’re headed somewhere other than Hawaii, California, or Florida. You’ll appreciate a waterproof Chelsea boot or a stylish snow boot if you get caught in a storm.

Slip-on Chelsea boots are also convenient in the airport security line.

Lucky Brand Women’s BASELH2O, Black, 9 Medium US
  • Even when the rain hits you’ll be…
  • Rainboots feature a waterproof…
  • Inside zipper closure with elastic…
  • Round-toe silhouette.
  • Textile lining. Lightly-padded,…
ARIAT Womens, Wexford Waterproof, Java, 7.5
  • COUNTRY-INSPIRED STYLE: The…
  • WATERPROOF PRO: To equip them for…
  • ATS TECHNOLOGY: For superior…
  • TWIN GORE STYLE: For easy entry and…
  • SCIENCE OF INNOVATION: Ariat excels…
Chaco Women’s Fields Chelsea Waterproof Boot, Chestnut Brown, 7
  • UPPER Full grain waterproof leather
  • Seam-sealed waterproof construction…
  • Women’s specific LUVSEAT PU midsole…
  • Non-marking ChacoGrip rubber…
  • 7mm Lug Depth

6. Crossbody

No one wants to haul around a clunky bag during vacation. The beauty of a crossbody bag is that you can slip it on and go about your business without a second thought. Going hands-free is just plain convenient, whether you’re fast-walking to your gate at the airport or meandering through local shops and attractions.

Telena Sling Bag for Women Vegan Leather Fanny Pack Crossbody/Chest Bag, Camel Brown
  • Large capacity – sling bag for…
  • High Quanlity Material – This small…
  • Multi-way to Carry – Benefit from…
  • Suitable for Various Occasion -…
  • Great Gifts Choice – Telena sling…
Gladdon Crossbody bags for Women Crossbody Purse Shoulder Bag Green
  • FUNCTIONAL: This Fashion…
  • EASY TO MAINTAIN: The small purse…
  • TRENDY: The high quality top metal…
  • THOUGHTFUL GIFT: This small…
  • This is truly the one that will be…
BOSTANTEN Crossbody Bags for Women Trendy Vegan Leather Hobo Purses Shoulder Handbags Wallet Set With Wide Shoulder Strap Coffee
  • High Quality Crossbody Bags: This…
  • Bags Structure: The interior…
  • Product Dimension: The size of this…
  • Wide Strap Designed: Our crossbody…
  • Best Gift Choice: This cross body…

7. Scarf

A scarf is a nice style addition, but it’s also an extra layer that can double as an airplane pillow. And just in case you don’t need it on the plane, choose one that’s small enough to shove inside your carry-on.

Sale
YSense Women’s Long Plaid Blanket Chunky Oversized Winter/Fall Warm Scarf Big Tartan Scarves Wrap Shawl, B-grey
  • Soft and Warm: Blanket scarf is…
  • Suitable Size: Our plaid scarf…
  • Design Feature: The color of…
  • Good Match: Plaid scarf easy to…
  • Your Choice: The womens scarf is a…

8. Packable jacket

Weather is unpredictable. But stashing a full coat in your weekender bag usually leaves room for nothing else. The solution? Try a packable puffer, which brings the warmth without the bulk.

SLOWTOWN Women’s Lightweight Puffer Jacket Packable Hooded Puffer Jacket Winter Puffy Jacket (Navy, Medium)
  • 🥰𝑬𝒂𝒔𝒚 𝒕𝒐…
  • 🥰𝑲𝒆𝒆𝒑…
  • 🥰𝑭𝒍𝒂𝒕𝒕𝒆𝒓𝒊…
  • 🥰𝑫𝒆𝒍𝒊𝒄𝒂𝒕𝒆…
  • 🥰𝑭𝒖𝒏𝒄𝒕𝒊𝒐𝒏…

What to wear while traveling: Other considerations

When choosing your perfect on-the-go travel outfit, keep these tips in mind:

  • Opt for supportive and easy-to-remove shoes.
  • Choose natural fabrics like cotton. They’re more breathable which feels better on longer journeys.
  • Skip the embellishments. Metal on your shoes, clothes, or belt can set off the metal detector in the airport.
  • Pockets are practical, but you want your stuff in zippable pockets. Don’t buy the sweater with big hip pockets if you’ll be tempted to use those pockets for cash or anything valuable.
  • Choose socks carefully. Opt for lighter socks so you don’t get overheated. You can rely on layers and a beanie to keep you warm instead. Compression socks can be great for long plane rides.

For more inspiration on what to wear while traveling, see my post about celebrity airport style.