Vacation is exciting. The travel may be a hassle when you wear the wrong clothes. Read what to wear on travel for comfort. No matter whether it is for play or work. No matter whether it is by plane, railroad, bus or car.
- What to Wear on Travel When on a Trip in Summer
- How to Dress for Travel in Winter from a Cold to Warm destination
- Best Shoes for Air Travel
- Winkle-free Clothes Are Key
- Easy Travel Outfits to Try for What to Wear on Travel
Disclosure: This post has affiliate links.
What to Wear on Travel When on a Trip in Summer
Of course, your outfit depends on the purpose of your trip. You have to dress differently when you are on a summer business trip than on a short summer weekend trip. Planning a summer vacation wardrobe strongly differs from packing for a short weekend get-away.
On a private for fun road trip in summer, what to wear depends on the outside conditions, and whether or not the car has air condition. If you expect the car to be cool, have a jacket handy. You can knot it around your waist when it gets too warm. So stylish. Dress for comfort with your plans in mind. Use wrinkle free, breathing and moisture wicking clothes.

When you drive in an open car or top-less Jeep, you absolutely need to put on a high SF sun screen. Wear sun-protective clothes to avoid getting a sunburn.
How to Dress for Travel in Winter from a Cold to Warm destination
For most of us living in climate regions with cold winters, winter travel to warmer regions is a challenge. For an Alaskan, it would mean schlepping a down coat around in Hawaii or Mexico, for instance, just because it is 40 below upon leaving or it might be that cold upon coming back. The best advice to solve this problem? Have someone bring to and pick you up at the airport who will take/bring the appropriate coat, shoes, gloves, scarf and hat.

Planes are often a little chilly as pilots turn the ventilation down to save fuel. Good thing for the environment! Your contribution should be to bring a blanket (you can later use it at the beach), light jacket, Chilly Jilly or a cardigan. Wearing a sweater over a T-shirt is also a good way to stay comfortable on the plane.
Summer Travel Look Inspiration
The next photos show a casual summer travel look that would work also on a summer business trip, when paired with a blazer.



Best Shoes for Air Travel
Wear shoes that you can easily take off/put on to not annoy everyone behind you in the security line. Thus, steer away from shoes with laces or buckles. Flip flops belong in the luggage, not on you feet while on travel. They just look cheap, and are a hassle to run in when you try to catch a connection. Furthermore, flip flops belong on the beach, not the airport. It is just against the dress code 😉 . Not to mention that they break every style except surfer beach style. Unless you can catch a bus running in heels or are a ballroom dancer, leave the heels for the female CEOs and managers in First Class or those women whose work dress code is corporate style.
Winkle-free Clothes Are Key
Since you have to sit on the plane, wear winkle-resistant clothes. Doing so is especially important when you dress and pack for a business trip. Your business partner(s) might pick you up at the airport, and you don’t want to look like you just rolled out of bed. Jersey dresses are a great for a professional, stylish look.




If you decide to wear jeans, go for a loose cut or a jeans with stretch. A 100% cotton jeans is just too uncomfortable when it digs its waistband into your belly. Steer away from sweat pants. They have their name for a reason. They belong into the gym. Yes, and please don’t wear PJs outside.
When your outfit asks for a belt, make sure you have it in your carry-on so you can finish your look once you are thru security.

Easy Travel Outfits to Try for What to Wear on Travel
Here are five comfy, but effortlessly stylish travel outfit ideas:
- Long sleeve tunic, long sweater or trench coat (have a long T-shirt underneath the trench because you may have to take it off) over leggings with ballet flats or pointy toe flats
- Loose jersey dress with cardigan and ballet/pointy toe flats or old school fabric sneakers
- Boyfriend jeans with sleek striped long sleeve T-shirt, printed wide scarf, and ballet flats or pointy toe flats
- Jeggings, long slouchy white T-shirt with black cable-knit long or grandpa knit-collar cardigan, light or open toe booties
- Loose printed skirt, ballet flats, matching (striped) T-shirt, cropped denim jacket or cardigan
The next photos show variations of the above suggestions.




When you like these outfit “recipes”, you may also want to get my style recipe book How to Dress for Success in Midlife for recipes for all kind of dressing situations. Buy it now.
Photos: G. Kramm
© 2013-2022 Nicole Mölders | All rights reserved