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This post of my Dress for Success series covers travel looks. Sure, vacation or meeting with family and friends whom you hadn’t seen for a long time is exciting. However, getting to the destination may be a hassle when you wear the wrong clothes. No matter whether your trip is for play or work. No matter whether it is by plane, railroad, bus or car or any combination thereof. Read what to wear on travel for wear and thermal comfort.

 

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What to Wear on Travel Is Not a One-Fits-All Answer

Of course, your outfit depends on the purpose of your trip, your transportation, the time of the year, the weather at the destination of your departure and arrival. You have to dress differently when you are on a summer business trip than on a short summer weekend trip for fun.

Furthermore, the duration of the trip plays a role including whether or not you will have to spend the night on the plane, train, in a camper, car or motel.

Speaking of this, recall that many intercontinental connections have long layovers at the airport. Instead of sleeping fully dressed on the chairs in the boarding are, sleep at a hotel near the airport. When you arrive at Chicago, for instance, and your next destination requires a comfortable stay, remember to book hotel in Lombard for a relaxing experience.

Furthermore, the pieces of your travel outfit have to work with the clothes you packed for the destination. Planning a summer vacation wardrobe strongly differs from packing for watching the aurora.

Now let’s discuss the points one at a time.

 

posh casual outfit ideas what to wear on travel in winter
First two outfit ideas are for flying to visit family. Boots c/o Flowfeet with Hipstik tights Left: Eddie Bauer skirt, GNW Luxe sweater. Left middle: Celtic & Co. kilt, Quince sweater. Two looks for a family road adventure: Middle left: GNW Luxe sweater, shearling hat, Hipstik tights, Lost Horizon knit skirt, Alohas boots. Right: Sanchez riding boots, Hipstik tights, Quince knit skirt, Anne Kleinsweater, DIY belt.

 

 

 

 

 

How to Dress for Travel from a Cold to Warm Destination in Winter

For most of us living in climate regions with cold winters, winter travel to a vacation resort in warm climate regions is a challenge. An Alaskan, for instance, has to schlep a down-coat around in Hawaii or Mexico, just because it is -40F (-40oC) upon leaving and/or it might be that cold upon coming back. The best advice to solve this problem?

Have someone to bring you to and pick you up at the airport who will take/bring the appropriate coat, shoes, gloves, scarf and hat.

 

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 charm-belt, structured work bag, floral tights, and Winkwood sunglasses.

 

fashion blogger over 50 showing what to wear on travel for comfort
What to wear on the plane when going on a private trip: Apricot double-breasted layered coat c/o Lookbook Store, 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.

 

How to Dress When Flying on Vacation or to a Family Reunion

When you travel by air, a comfy, dressed-up casual look is fine.

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, or a cardigan. Wearing a sweater over a T-shirt is also a good way to stay comfortable on the plane. Go for loose pants.

When you 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 and belong into the gym. Yes, and please don’t wear PJs outside.

Tip: 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.

 

 

What Are the Best Shoes to Wear for Air Travel?

Wear shoes that you can easily take off/put on to not annoy everyone behind you in the security line. Therefore, steer away from shoes with laces or buckles. Booties or boots with zipper closure, driving shoes, loafers, ballet flats are easy to slip off and on.

Flip flops belong in the luggage for the beach, not on you feet while on travel. They just look cheap, and wearing flip flops in the airport is just against the dress code. Not to mention that they break every style except surfer-beach style. Furthermore, flip flops like mules, slides, clogs are a hassle to run in when you try to catch a connection.

Tip: Because sometimes you might miss a connection, always have your PJs in your carry-on.

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 for Work Trips

Because 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.

Tip: Wear garments in wool or wool blends. Because wool is wrinkle-resistant, cotton or hemp attire with just a small wool percentage (5-10%) already is enough to avoid wrinkles.

 

 

3 work trip outfit ideas with travel dresses for different seasons
Business trip style for winter, summer, fall/spring. Left: 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. Note that the lace-up detail is just for style. Middle: Karina Dresses fit-and-flare dress, Tommy Hilfiger sandals, Jord men’s watch, Hermes collier de chien bangle, Kieselstein Cord crocodile-imprinted belt, sunnies c/o glassesonline.com, and bag c/o thirty-one. Right: 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 bamboo watch, vintage bangle, and halftee c/o Halftee.

 

Looks to Wear When on a Journey by Rail Road

If the rail road voyage is from Coast-to-Coast, thru Europe or the Trans-Siberian Rail Road, you have your baggage in your cabin. Therefore, you best bet is to dress for the weather at the station of departure. Because you will take breakfast, lunch and dinner in the train’s restaurant comfortable, but preppy outfits are fine unless the flier of the agency indicates a dress code.

When your rail-road journey is for fun and short-like going from Albany, NY to Central Station, comfortable casual layered look is best. It namely allows you to adjust to the temperature when the AC is over-performing or doesn’t work at all. The latter happened when my friends and I went on a sightseeing trip to New York in 1989.

 

fashion blogger over 50 in casual denim look
Air plane or railroad 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, Hermes H-buckle. If you cannot run in heels, swap for slip-on flat tan sandals.

 

style blogger in a dress with jacket for business traveling
Baby-pink dress c/o Lookbook Store worn with 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.

 

 

How to Dress When Traveling by Car

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. 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.

When you plan to eat in a restaurant instead at a fast-food chain, go for a comfortable, but posh casual or preppy style.

 

Tip: Use wrinkle-free, breathing and moisture wicking clothes.

traveler enjoying a break in front of a hotel
Chena with view on the Princess Hotel in Fairbanks and the White Mountains in the background. Oliveo straight linen pants, Kieselstein Cord belt, 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, best girlfriend bracelet and V-neck top both c/o Chico’s. This casual summer travel look would work also on a work trip for an environmental scientist or employee of the business casual world when paired with a blazer.

 

Easy Outfit Ideas to Try for What to Wear on Travel for Fun

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

 

mature woman in casual, stylish outfit
Printed cotton 3/4 sleeve GNW cardigan, Oliveo linen pants, Anne Klein sling backs, Kieselstein Cord belt, 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 belt and sling backs. Swap the heels for nude pointy toe flats.

 

What to Wear When on a Bus Tour?

On a bus, you aren’t in control of the AC. Therefore, a layered look serves you best. Because you are not in private on a bus, go for an upscale version of the outfits for a car ride.

 

3 outfit ideas showing what to wear on travel with the rail road or overland bus
Outfit ideas for a short rail road or overland bus tour. Left: Middle: T-shirt c/o Marine Layer, Oliveo linen pants, Great Northwest denim jacket, belt, Nicole suede fall sandals, and Kate Moss for Longchamp satchel. Right: Great Northwest denim shirt with VS motorcycle leather vest, chinos, Ray Ban mirrored sunglasses, Jaeger tote, and Ralph Lauren shoes.

 

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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