We independently evaluate all of our recommendations. If you click on links we provide, we may receive compensation. The 5 Best Travel Outfits for Long-Haul Flights and Cross-Country Road Trips, According to a Style Editor Cute yet comfortable is our strategy. Published on May 16, 2026 By Alison Syrett Cleary Alison used her experience as a fashion editor-turned-travel writer who flies multiple times a month to create these stylish outfit picks. In This Article View All In This Article Top Picks Reviews Why Shop With Us Credit: InStyle Best Sweatpant Alternative: A thoughtfully chosen pair of drawstring pants in an interesting color or material can drastically improve a travel outfit. Mango’s Bow Straight Trousers look more elevated than sweats without sacrificing comfort. Go-With-Anything T-shirt: If you’re going to wear a T-shirt, pay extra attention to how its fabric holds its shape over several hours. I recommend Uniqlo’s Mini T-shirt for its thicker material, closer-fit cut, and budget-friendly price. Editor-Favorite Walking Shoes: Sneakers aren’t the only footwear suitable for walking. Try a slip-on shoe, like the Birkenstock Boston Chunky Clogs, or ballet flats, like J.Crew’s Sophie Flats. What makes a travel outfit good? Honestly, it depends on who you ask: Some people refuse to embark on a long-haul commute in anything but leggings, while others are just fine in slacks and a button-down. But for me, a fashion editor who has recently segued into the world of travel journalism, I’d say the sweet spot falls somewhere in between: What I wear when embarking on a trip is essentially the most comfortable version of my everyday wardrobe. Styling duo Rebecca Klein and Martina Gordon tell me they recommend travel-friendly pieces that are “comfortable, easy, chic, and don’t wrinkle.” Stylist Jenni Lee is of a similar mind: “The ideal travel outfit makes zero compromises between being comfortable and feeling put together,” she says. With the help of style experts, I’ve pulled together five bulletproof formulas for flights, train journeys, and road trips, below. And, because I’m nothing if not a consummate fashion reporter, I’ve tried the exact pieces myself—so you can trust that these outfits are editor-approved. Top Picks Colorful Cotton Pants: Leset Carpenter Pant at Leset.com $280 Jump to Review Reliable Ballet Flats: J.Crew Sophie Ballet Flats at J. Crew $148 Jump to Review Pair-With-Anything White T-Shirt: Uniqlo Mini T-shirt at Uniqlo.com $15 Jump to Review Most Comfortable Jeans: SALE Madewell The Low-Slung Baggy Jean in Airy Denim at Madewell.com $158 $120 Jump to Review A Chic Trench Coat: Banana Republic Trench Coat at Banana Republic $400 Jump to Review Security-Friendly Slip-On Clogs: Birkenstock Boston Chunky Clogs at Nordstrom $155 Jump to Review Classic Sweats: SALE GAP VintageSoft Relaxed Joggers at Gap $60 $29 Jump to Review Dua Lipa-Approved Sneakers: Puma Speedcat OG at Nordstrom $110 Jump to Review A Trending Pant Style: SALE Old Navy Poplin Balloon Pants at Old Navy $50 $25 Jump to Review Feminine Walking Shoes: Vivaia Square-Toe Lace-Up Sneakerinas at Vivaia.com $159 Jump to Review The Bright Travel Look: Drawstring pants, a baby tee, a cardigan, and ballet flats InStyle Drawstring pants for travel…wow, groundbreaking, right? It actually feels that way, though, if you go for a pair in an unexpected color. I love this sunny butter yellow shade, but the style also comes in other vivid shades like grass green and soft pink. Pair the comfortable pants with layered tops that hit right at or above the waistband. This will break up your proportions in a way that really makes the look seem intentional. Pro tip: A boxier cardigan will lay nicely with something fitted underneath. Ballet flats are comfortable enough for walking or waiting in long lines, and they look much more sophisticated than sneakers. Leset Carpenter Pant $280 at Leset.com Cos Merino Wool Cardigan $149 at Cos.com J.Crew Sophie Ballet Flats $148 at J. Crew Uniqlo Mini T-shirt $15 at Uniqlo.com The Elevated, Straight-Off-the-Plane Look: Baggy jeans, a tank, a jacket, and derbies InStyle For all the hate jeans get regarding travel—especially air travel—I actually prefer them for durability and warmth. The key is to pick a design that’s very relaxed and doesn’t sit too high on the waist, which can feel uncomfortable when you’re sitting for a long time. Wearing jeans on the plane also pays off if you can’t immediately check into your hotel room to shower and change, as it looks pulled together from the get-go, especially if you follow Klein and Gordon’s advice of wearing a soft, stretchy top with a structured jacket on top. (It instantly elevates the look after a long flight, they say.) I’d suggest taking things a step further with menswear-inspired shoes, like these derbies. They have all the durability and stability of loafers, but are a less obvious choice. Alex Mill Soho Jacket $250 at Alexmill.com Madewell The Low-Slung Baggy Jean in Airy Denim $158 $120 at Madewell.com Nomasei Sonics Derby $630 at Nomasei.com Abercrombie & Fitch Paloma Top $40 $32 at Abercrombie.com The Anti-Sweatpant Look: Baggy jeans, a tank, a jacket, and derbies InStyle A cheat code if you are loath to wear loungewear in public: Pick a drawstring trouser made from a traditionally “dressy” fabric like wool, satin, or cashmere. It will elevate your plane outfit, especially if you add a fitted sweater and classic trench coat. This ensemble is reminiscent of Lee’s go-to travel look: “a fluid, silky pant with a coordinating top or fitted tee.” I’d finish the look with a slide, but one that’s unexpectedly cool—a platform version of the timeless (and orthopedic) Birkenstock Boston should do the trick. Everlane Cropped Crew Top $128 at Everlane.com Mango Bow Straight Trousers $60 at Mango.com Banana Republic Trench Coat $400 at Banana Republic Birkenstock Boston Chunky Clogs $155 at Nordstrom Editor-Approved Sweatpant Styling: Sweatpants, a long-sleeve T-shirt, a leather jacket, and colorful sneakers InStyle If you must wear sweats and sneakers, Lee advises being extra intentional with the designs you choose—especially in your footwear. “Shoes make or break everything,” she says, suggesting a “clean low-top or platform sneaker” if you want to go the athletic footwear route. Klein and Gordon agree, vouching for elevated sneakers instead of running shoes. Sweats, Lee says, are doable as well: She’s into a full-on coordinating sweat set in a bold color or print. Meanwhile, my go-to method is to contrast the softer bottom with something tough up top, like a leather jacket. Buck Mason Surplus Rib L/S Crew $88 at Buckmason.com GAP VintageSoft Relaxed Joggers $60 $29 at Gap GU Global Harrington Jacket $60 at Gu-global.com Puma Speedcat OG $110 at Nordstrom The Sweet and Sporty Airport ‘Fit: Track pants, a rugby top, a baseball cap, and ballet sneakers InStyle Track pants have been having a moment for a while, thanks to appearances on runways (see: Tory Burch) and celebrities (Hailey Bieber’s a big fan). So, why not utilize the no-fuss style’s relevance for a long trip? I suggest leaning into the sporty vibe with a rugby top, baseball cap, and ballerina-inspired sneakers—both major trends floating around the fashion zeitgeist. Old Navy Poplin Balloon Pants $50 $25 at Old Navy Vivaia Square-Toe Lace-Up Sneakerinas $159 at Vivaia.com Aritzia Mighty Cotton Lomu Polo Longsleeve $68 at Aritzia.com FRAME Baseball Cap $148 at Shopbop.com Why Shop With Us Alison Syrett Cleary is a fashion journalist with over a decade of industry experience, covering topics such as personal style, shopping recommendations, and emerging trends. She also writes about travel both for multiple outlets and her newsletter Take It To Go, and flies internationally at least once—if not twice or three times—a month for work. For this story, she spoke to the following experts: Rebecca Klein and Martina Gordon are former models and a styling duo. They both frequently fly for work and have many frequent flyer styling clients.Jenni Lee is a stylist and the founder of Style Club. She specializes in helping real women find smart and chic wardrobe solutions for every facet of their lives—including all kinds of travel. Read more: Shopping