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The Best (and Worst!) Things to Wear When Traveling

Pulled-together and comfortable outfits for every adventure


different things to wear
(From left) H&M Women Tie-Belt Viscose Shirtdress in Black/Cream Patterned; Gap Factory’s Women Linen-Blend Easy Shirt in Optic White; Toni Pons Women Estel Espadrille Sandal in Platinum Fabric; Rothy’s Casual Crossbody in Night Song; Quince 100% Organic Cotton Knit Blazer in Navy.
AARP (H&M, Gap Factory, Nordstrom, Rothy’s, Quince, Getty Images)

Have you ever gotten a snooty once-over from a tour guide or an airline ticket agent? Been so uncomfortable and cold on a plane, you couldn’t wait to land? Felt underdressed when sightseeing? Regretted wearing tight jeans and boots on a road trip? Arrived on a business trip looking like you slept in your clothes? Travel outfits can make or break any trip. As a fashion editor, stylist and personal shopper for women over 50, I know what to wear to prevent situations like these — it's my specialty. Here are the best and worst picks for all. You’re on your way!

different things to wear
(From left) Ann Taylor Weekend Collection Striped Knit Jacket in Winter White-Black; Gap Factory Women High Rise Ponte Flare Crop Pants in Black; Vanity Fair’s Body Caress Full Coverage Wireless Bra; Vionic Uptown Skimmer Knit Slip-On in Black
AARP (Ann Taylor, Gap Factory, Macy’s, DSW)

1. For the plane/airport

Despite expedited security clearance, online check-in and preflight seat selection, days at the airport never go as planned. No matter where you’re headed, there are delays, cancellations and gate changes. Looking pulled-together but feeling comfy can de-stress any situation and possibly snag you better service.

The worst things to wear: Any clothing that invites discomfort, such as tailored zip-front pants and tight jeans, or signals a TSA pat-down, like cargo pants and voluminous skirts, is a definite no. So are bodysuits and jumpsuits that prevent getting in and out of the restroom quickly. That also goes for mules or slides that make racing to the gate a gamble. Also on the don’t-wear-this-on-planes list: midi dresses, maxi skirts and summery sandals (you’ll be extremely cold!); underwire bras and boots (breasts, legs and feet swell on board); and scents that might trigger an allergic reaction in your seatmate.

The best things to wear: Leave your baby blue joggers and heavy winter sweaters at home. Light layers in neutrals like black, white, navy and tan are the key to temperature control and giving casual outfits a classy look. One foolproof strategy combines pull-on pants like the Gap Factory Women High Rise Ponte Flare Crop Pants in Black Marl or Black ($36, gapfactory.com), a long-sleeve tee such as the Gap Modern Crewneck T-Shirt in Black ($14, gap.com), a light sweater like the Banana Republic Factory Women V-Neck Pullover in Snow Day or Black ($34, bananarepublicfactory.gapfactory.com), which can be worn or stylishly wrapped over the shoulders, and a knit jacket such as the Ann Taylor Weekend Collection Striped Knit Jacket in Winter White-Black ($39, anntaylor.com). You can also manage in-flight bloat and swelling by wearing a wire-free bra like Vanity Fair’s Body Caress Full Coverage Wireless Bra ($48, macys.com), slip-on shoes like the Vionic Uptown Skimmer Knit Slip-On in Black ($130, dsw.com) and, for those with circulation issues, a pair of light compression socks.

different things to wear
(From left) Mango’s Striped Round-Neck Sweatshirt in Navy; Old Navy High-Waisted Weekender Pull-On Crop Wide-Leg Jeans in Dark Gray; Lands’ End Women’s 3/4 Sleeve Lightweight Jersey Tunic in White.
AARP (Mango, Old Navy, Lands’ End)

2. For a road trip

Car travel can be challenging, whether you’re headed cross-country to see the Grand Canyon, taking a scenic drive along the coast, or on the way to a countryside B&B. As a driver or a passenger, you will spend hours sitting in a confined space and shape (I don’t care how roomy your SUV is!), often with the AC or heat blasting.

The worst things to wear: Do your body a favor and don’t drive in snug or non-stretch jeans. The stiff, scratchy fabric and tight fit will get to you. The same goes for loose, flowy dresses, platform shoes, wedges and heavy sneakers. Remember that your legs, ankles and feet can swell when sitting for hours in a car (just like on a plane!).

The best things to wear: Once again, stick with upscale neutrals, because a well-dressed presentation at rest stops, restaurants and on-arrival counts. Plan for a relaxed mix of basics and athleisure. Start with soft joggers or pull-on stretch jeans like the Old Navy High-Waisted Weekender Pull-On Crop Wide-Leg Jeans in Dark Gray or Black ($26, oldnavy.gap.com) and a lightweight tee like the Lands’ End Women’s 3/4 Sleeve Lightweight Jersey Tunic in White ($43, macys.com). Then add a relaxed sweater such as the L.L. Bean Women’s Unwashed Waffle Sweater in Classic Navy ($60, llbean.com) or an elevated sweatshirt like Mango’s Striped Round-Neck Sweatshirt in Navy ($50, mango.com) and light, no-need-to-lace-up sneakers like the Sperry Crest Vibe Slip-On Sneaker in Black Fabric ($70, nordstrom.com).

different things to wear
(From left) Old Navy Women High-Waisted Linen-Blend Wide-Leg Pants in Indigo; Banana Republic Women High-Rise Wide-Leg Cropped Pull-On Pant in Black; Gap Factory’s Women Linen-Blend Easy Shirt in Optic White; Toni Pons Women Estel Espadrille Sandal in Platinum Fabric.
AARP (Old Navy, Banana Republic, Gap Factory, Nordstrom)

3. For hot climates

No matter how fabulous the destination, intense heat and steamy weather bring another set of problems on arrival. For many women, the dilemma is how to stay cool and sweatproof without exposing too much skin while traveling. This is especially true in conservative destinations with a more modest dress code.

The worst things to wear: Skip anything tight like leggings or skinny jeans, fitted dresses, clingy tops and heavy, occlusive or synthetic fabrics like faux leather, nylon, polyester and satin that will promote a meltdown. The same goes for revealing clothing like shorts, slim and leg-baring skirts, tank tops and deep-V necklines that will attract the wrong kind of attention. In fact, if it’s too bare, too skimpy, too short or too sheer, just say no. You want to avoid wearing anything that can appear offensive or disrespectful in conservative countries.

The best things to wear: Whether you’re headed to Morocco, Egypt, Mexico or steamy New Orleans, count on breathable fabrics like cotton and linen to keep air circulating and a fresh look going. Light tees such as the cotton Everlane The Air Long-Sleeve Tee in Black or Navy ($45, everlane.com), linen shirts like Gap Factory’s Women Linen-Blend Easy Shirt in Optic White ($36, gapfactory.com), and loose-fitting pants like the Banana Republic Women High-Rise Wide-Leg Cropped Pull-On Pant in Black ($130, bananarepublic.gap.com) and the Old Navy Women High-Waisted Linen-Blend Wide-Leg Pants in Indigo ($28, oldnavy.gap.com) are your best bet, day and night. Note that dark neutrals and white hide sweat stains better than pastels and brights. You’ll want to add comfy, airy walking shoes like the Toni Pons Women Estel Espadrille Sandal in Black Fabric or Platinum Fabric ($120, nordstrom.com) and a lightweight scarf or shawl to cover your head and shoulders (especially if wearing a sleeveless top or dress) at religious sites.

different things to wear
(From left) J. Crew Factory Wide-Leg Crop Jean in All Day Stretch in Seashell White; Boden Chloe Jersey Midi Dress in Black; H&M Women Tie-Belt Viscose Shirtdress in Black/Cream Patterned.
AARP (J. Crew, Boden, H&M)

4. For big cities around the world

Movies and TV series set in foreign locations — like Emily in Paris — always show women wearing the most glammed-up clothes. If you’re thinking this is the way to look like a local, it’s not. You want to dress to blend in, not stand out. Not only will you get better service, but you won’t be an easy target for pickpockets on streets and public transit.

The worst things to wear: Don’t be a billboard or overly casual. Anything with large logos or slogans (even your favorite team or brand), workout clothes, especially sweatpants and leggings, baseball caps and visors, big bulky white sneakers and ripped jeans will look out of place. Leave your good or flashier pieces of jewelry at home (diamonds, expensive watches and dangly earrings are lures for muggers), and avoid wearing big-ticket designer accessories head to toe. That showy LV tote or open-top Gucci bag? Don’t.

The best things to wear: While jeans and midi dresses are pretty much a uniform everywhere these days, take the polished route with jeans in crisp black or white, like the J.Crew Factory Wide-Leg Crop Jean in All Day Stretch in Seashell White ($70, factory.jcrew.com) and midi-length dresses in black or black prints like the H&M Women Tie-Belt Viscose Shirtdress in Black/Cream Patterned ($35, hm.com) and the Boden Chloe Jersey Midi Dress in Black ($98, us.boden.com) that offer leg coverage and look sophisticated day and night. Carry or wear a refined cardigan like the A New Day Duster Cardigan in Oatmeal, Black or Taupe ($17, target.com) for coverage and to elevate anything as needed, and a just-the-right-size crossbody bag such as Rothy’s Casual Crossbody in Night Song ($169, rothys.com).

different things to wear
(From left) Aqua Cashmere Drape Front Cardigan in Mushroom; Ann Taylor Weekend Collection Voile Drawstring Midi Skirt in Black; Gap Factory Women Mid Rise Linen-Blend Pull-On Wide-Leg Pants in Black.
AARP (Bloomingdales, Ann Taylor, Gap Factory)

5. For sightseeing

The success of what seems like an ideally planned day depends a lot on what you wear … and where you wear it. Some destinations are very conservative, while others have a looser, more relaxed dress code. You may be cruising around the Greek Islands, oohing and ahhing at Versailles, visiting dazzling street markets in Italy, riding a camel while checking out the Pyramids at Giza or roaming Gaudi’s Sagrada Familia in Barcelona. Being prepared to pivot or change your itinerary and feeling well-dressed enough not to think twice about your clothes is the point.

The worst things to wear: Avoid sporty clothes like leggings, hoodies and the kinds of tees you’d wear to see a tribute band at home. Skip backpacks, large tote bags and other bags with an open top; carrying a smaller bag prevents you from bumping into people in crowds while sightseeing. Wear the right clothes for the right place. You don’t need deep scoop or plunge necklines for a wine tasting or an archeological tour. Don’t wear brand-new shoes or sandals. If you haven’t done a dry run at home and broken them in, this is not the moment to start.

The best things to wear: Consider options that allow you to pivot — from climbing hundreds of steps, to lunch at a local cooking class, to checking out ancient ruins, to attending a concert — without a change of clothes. This is where a midi skirt like the Ann Taylor Weekend Collection Voile Drawstring Midi Skirt in Black ($97, anntaylor.com) can give a practical but fashionable look to a tee, a sweater like the Aqua Cashmere Drape Front Cardigan in Ivory, Camel or Mushroom ($80, bloomingdales.com), and rubber-soled slip-ons like the Michael Kors Nori Espadrille Flat in Cognac or Black ($95, dsw.com). Not a skirt person? Swap in black linen pants like the Gap Factory Women Mid Rise Linen-Blend Pull-On Wide-Leg Pants in Black ($42, gapfactory.com) for an equally chic alternative.

different things to wear
(From left) Lauren Ralph Lauren Sweater-Knit Blazer in Black; Quince 100% Organic Cotton Knit Blazer in Navy; Banana Republic Ribbed Crew-Neck T-Shirt in Black.
AARP (Bloomingdales, Quince, Banana Republic)

6. For a business trip

Traveling for work can be tricky. Women say they often need to sprint straight from the plane to a meeting or a presentation and on to dinner without a chance to change clothes or freshen up. The longer the flight, the comfier and more relaxed you will want to be. Sometimes, you may be traveling with work colleagues or senior management. This makes showing up barefaced and doing makeup and an outfit switch in the restroom before landing not a great idea. It is possible to pull together a stylish and professional look that’s almost as homey as sweats.

The worst things to wear: Say no to skirt suits, dresses and heels. They limit how you sit and walk. The same goes for any item of clothing like belts, tucked-in tops and bodysuits that require adjustment as the day goes on, or garments that wilt, like blouses.

The best things to wear: It’s a fashion fact of life that the sharp lines of tailored clothes can make you appear crisp, wide awake and trim. But it’s when tailoring meets travel-friendly stretch fabrics and knits that the real style magic happens. Just take a knit blazer like the Lauren Ralph Lauren Sweater-Knit Blazer in Tan, Lauren Navy or Black ($146, bloomingdales.com) or Quince 100% Organic Cotton Knit Blazer in Navy ($80, quince.com) if you prefer a pop of color, and add black pull-on ponte pants like Talbots Luxe Ponte Flare Leg Pants in Black ($139, talbots.com). You will have created a modern, unstuffy “suit” look that defies hours of wear with the feel of a sweater and leggings, even on long-haul flights. Add a sleek long-sleeve tee like the Banana Republic Ribbed Crew-Neck T-Shirt in White or Black ($55, bananarepublic.gap.com) in stretch cotton with a hint of silky modal to keep the wrinkle-free effect going. Dressy casual is more your thing? Try Chico’s No Iron Linen Shirt in Optic White or Indigo ($67, chicos.com) over the Ponte pants and take a trench coat as a topper. Iron-free shirts look great untucked and function as tunics. In white or blue, they are guaranteed complexion brighteners that erase fatigue. Black flats rule here; no excuses.

different things to wear
(From left) Ann Taylor Weekend Collection Denim Jacket in Ivory; Lands’ End Women Squall Packable Rain Jacket in White.
AARP (Ann Taylor, Lands’ End)

7. For unpredictable weather

Whether you’re cruising down the Danube, strolling the Tuileries in Paris or taking a girls’ trip to Santa Fe with your besties, you can’t count on the weather. It’s the same story as when you’re home, only without the extra umbrella, raincoat or sweater available to grab in a flash from your closet, tote bag or car.

The worst things to wear: How many pairs of leather shoes have you wrecked in the rain on a trip? Or days when the forecast said “thunderstorms,” but blue skies persuaded you to leave a jacket or umbrella behind? Maybe the day seemed gloriously warm, so you opted for a short-sleeved tee, but a few hours of museums felt more like a trek in Antarctica. Never risk suede on a trip. It will not recover. Been there!

The best things to wear: Gray skies? You can’t lose with weather-resistant espadrilles like Skechers Flexpadrille Espadrille Flat in Black ($50, dsw.com) with a flexible traction rubber sole, or waterproof shoes like Blondo Erni Waterproof Flats in Black Leather or Sand Leather ($110, zappos.com) with a rubber outsole that prevents slips on slippery wet steps. And don’t overlook taking a lightweight hooded waterproof jacket like the Lands’ End Women Squall Packable Rain Jacket in White ($100, landsend.com). You can even add it as the jacket layer of your “plane” outfit. You won’t be scrambling to buy an umbrella or dash for cover. Prefer a tasteful jacket that’s not a blazer? Consider an elevated denim jacket like the Ann Taylor Weekend Collection Denim Jacket in Ivory ($97, anntaylor.com), which has a “lady jacket” vibe, or a cropped trench like the Old Navy Women Oversized Double-Breasted Short Trench Coat in A Stone’s Throw ($36, oldnavy.gap.com), which has the glamour of the full-length version. Both chill cheaters look posh day or night.

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