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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.


  1. What to Wear on Travel When on a Trip in Summer
  2. How to Dress for Travel in Winter from a Cold to Warm destination
  3. Best Shoes for Air Travel
  4. Winkle-free Clothes Are Key
  5. Easy Travel Outfits to Try for What to Wear on Travel


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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.


stylist showing what to wear on travel donning a Marine Layer striped T-shirt, denimim jacket, linen pants
T-shirt c/o Marine Layer with own Oliveo linen pants, Great Northwest denim jacket, belt,  Nicole suede fall sandals, and Kate Moss for Longchamp satchel


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.


fashion blogger over 50 showing what to wear on travel for comfort
Apricot double-breasted layered coat c/o Lookbook Store paired with own J Brand jeans, black mock neck top and snake print Anne Klein sling backs. Unless you are a ballroom dancer swap them for pointy toe or ballet flats


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.


mature fashion blogger in linen pants and top travel outfit
Oliveo straight linen pants, Kieselstein Cord belt and buckle, Dooney and Bourke tote, Esprit neckerchief, Hermes collier de chien bangle, Ray Ban sunglasses, Anne Klein AK logo open-toe pumps, charm necklace and earrings (all own), best girlfriend bracelet and V-neck top both c/o Chico’s


Nicole in travel outfit standing at the water
Side view of the above summer travel outfit to show the long tail of the top.


fashionista enjoying time off in front of a hotel
Chena River with view on the Princess Hotel and the White Mountains in the background. Oliveo straight linen jean-cut pants, Kieselstein Cord belt and buckle, Ray Ban sunglasses, Dooney and Bourke tote, Esprit neckerchief, Anne Klein pumps, charm necklace and earrings, V-neck top c/o Chico’s


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.

Nicole in denim coat, patterned tights, wooden sunglasses business travel look
Max Mara denim coat with fur details, eShakti fit-and-flare jersey dress, Judith Leiber charmbelt, structured work bag, floral tights, and Winkwood sunglasses


midlife blogger in floral jersey dress with pointy toe heels and trench coat for a work trip
Karina Dresses boat neck dress in navy with red abstract floral print, Anne Klein nude pointy toe pumps, and Burberry Brit trench coat, Hermes collier de chien bangle, Jord wooden bamboo watch, vintage bangle, and halftee c/o Halftee


Nicole of High Latitude Style walking in professional blue and white jersey clothing
Pantyhose, Fendi boots, graphic brooches from my late Granny Hannah, Judy Goom rabbit brooch, baroque and mixed size pearl necklaces, Hermes collier de chien bangle, Festina sports watch, Akoya saltwater pearl necklace c/o The Pearl Source Inc., layering top c/o Halftee, and Samantha Brown faux wrap dress c/o HSN


traveler in jersey dress with shoulder strap tote
Karina Dresses  fit-and-flare dress, Tommy Hilfiger sandels, Jord men’s watch, Hermes collier de chien bangle, Kieselstein Cord crocodile imprinted belt, sunnies c/o, and bag c/o thirty-one


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.


fashion blogger over 50 in casual denim look
Business casual travel look: Liz Claiborne denim dress and Great Northwest jacket in different wash, Kate Moss for Longchamp bag, Anne Klein T-straps slip-on shoes, Hermes collier de chien bangle, pantyhose, Kieselstein Cord belt and Hermes H-buckle. If you cannot run in heels, swap for slip-on flat tan sandals




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.

style blogger in casual travel outfit with denim shirt and chinos
Great Northwest denim shirt with VS motorcycle leather vest, chinos, Ray Ban mirrored sunglasses, Jaeger tote, statement belt and Ralph Lauren silver shoes


style blogger in a dress with jacket for business traveling
Baby pink dress c/o Lookbook Store worn with own light blue tailored denim jacket, an Esprit vintage bag, Madonna True or Dare floral pumps, and a DIY necklace. If you cannot run in heels, swap the pumps for pointy toe flats, floral print Keds or Vans


maturestyle woman in casual, stylish outfit
Printed cotton 3/4 sleeve GNW cardigan (own) with Oliveo linen pants, Anne Klein slingbacks, Kieselstein Cord belt and buckle, Esprit bag, and black silk top. The black color of the top and the black in the print pick up the black weave in the linen pants. The brown hues in the cardigan pick up the hue of the Kieselstein Cord belt and slingbacks. Swap the heels for nude pointy toe flats


Mature casual outfit with chinos and denim jacket
Oversize Great Northwest denim jacket over black cashmere sweater with Oliveo chinos, Anne Klein silk scarf, statement belt, Ray Ban mirrored sunglasses, Ralph Lauren silver shoes, and structured bag



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

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