For All Your Trips on Planes, Trains, and Automobiles
Traveling the world is exhilarating—but let’s be real, it can also be exhausting. The last thing you should have to stress over? What to wear while you’re getting from A to B.
Below you’ll find three of my favorite go-to travel outfits, perfect for every type of trip, along with direct links so you can snag the exact same pieces on Amazon.
And because I love a good finishing touch, I’ve also included a few bonus staples and the best travel accessories to complete your look—so you can arrive feeling comfortable, rested, and ready for whatever adventure comes next.
A Quick Heads-Up Before We Shop
I’m an Amazon Associate, which means I earn a small commission if you buy something through the links below. It doesn’t change the price you pay — it just helps me keep the coffee flowing and the travel stories coming. A girl’s gotta eat, right?
Find Your Fit
Click below to jump straight to the outfit that matches your travel plans—or head to the bonus round for extra pieces and accessories I swear by.
Outfit #1: Comfy, Stylish, and Warm
For those shorter travel days when you can land, drop your bags, and step straight into sightseeing mode—and at least one end of your journey has a chill in the air.
Best for late fall through early winter.
You want something cozy enough for the journey, but stylish enough to stroll into a café, museum, or wine bar without feeling underdressed. Layering is key here: warm enough for frosty sidewalks, but easy to peel off when you’re packed into a plane like sardines. This outfit delivers—snuggly, chic, and ready for whatever the day (or the weather) throws your way.
My Favorite Travel Jeans
These Levi Strauss Totally Shaping Pull-On Skinny Jeans hit the sweet spot between fitted and comfortable — slim enough to work with boots, sneakers, or sandals, but not so tight you feel like you’re in denim prison. The pull-on waistband means no digging or pinching while you’re crammed in a seat, and the bit of stretch makes moving (and napping) a breeze. Best of all? Real pockets. All of them. None of that fake-pocket nonsense.
A Cozy Sweater That Keeps You Warm Without Overheating
When you’re traveling, there’s a fine line between “snug and happy” and “slowly roasting like a human baked potato.” This Prettygarden cardigan nails it — soft and blanket-y without turning you into a sweat lodge. It’s perfect for airports, train rides, and chilly café patios, and comes in colors ranging from classy neutrals to “spot me from across the terminal.” Dress it up, dress it down, and most importantly, re-wear it without anyone realizing you’ve basically moved in.
A Waterproof Coat Light Enough for Spring & Fall, and Warm Enough for Winter
This Eddie Bauer Cloud Cap Stretch Coat has been my ride-or-die outerwear from blizzards in Iceland to drizzly spring mornings in Kyoto. It packs down small, layers like a dream, and stretches just enough for a comfy fit (no stiff, marshmallow-man vibes here). Waterproof? Check. Hooded? Check. Warm enough for zero degrees yet somehow not stifling at fifty? I’m convinced it’s stitched with sorcery.
The Boots I Wear Everywhere
These Jellypop Moto Boots are my secret weapon for looking pulled-together while secretly prioritizing comfort. I’ve worn them pounding the pavement in big cities, splashing through puddles, and—on one memorable detour—snowshoeing on the Continental Divide. (Zero regrets, 10/10 performance.) They’re water-resistant enough to handle surprise slush, cushy enough for all-day wear, and rugged enough that I don’t have to baby them. If they ever stop making these, I might have to start a boot hoarding operation.
Outfit #2: Comfy, Stylish, and Cool
For those travel days when the adventure starts immediately—no hotel check-in, no quick change, just straight from the gate to the good stuff.
Best for late spring through early fall, when at least one end of your trip is serving up that hot-and-humid weather.
You want something that won’t pinch, twist, or annoy you while you’re on the move, but still looks put-together enough to hop off the plane and dive right into sightseeing, lunching, or lounging with locals. Warm-weather travel calls for light, airy fabrics that breathe, paired with smart layers to fend off the overzealous airport AC. This outfit nails that balance—cute, comfy, and ready to roll.
Some of the Greatest Travel Pants of All Time
The North Face Aphrodite 2.0 Pants are the rare unicorn that’s equal parts flight-day lounge wear, trail-ready gear, and “yes, I’ll have another glass of wine” dinner attire. They’re water-resistant, quick-drying, and breathable with just the right amount of stretch—so you can hike, sprint to your gate, or sit cross-legged for eight hours without regret. Bonus points for the UPF protection and sink-wash-and-dry ease (a lifesaver when you spill coffee on yourself in hour one of a 12-hour layover).
The Best Tank Top – With a Built-In Comfy Shelf Bra!
The Hibelle Racerback Tank Top is the holy grail of travel tops: light padding for just enough shape, a built-in shelf bra that doesn’t feel like a medieval torture device, and a loose-but-flattering fit that hides your post-vacation pasta belly without adding phantom pounds. And the colors? Endless. Patterns? Adorable. My personal collection? Four and counting.
A Light Wrap That’s Perfect for Layering – On and Off the Plane
After a decade of loyal service, my beloved Eddie Bauer travel wrap finally met its match — or at least, its doppelgänger. This nearly identical Newchoice Lightweight Long Sleeve Cardigan (available in 35 colors!) hasn’t clocked as many passport stamps yet, but it’s already earned a permanent spot in my carry-on. It’s featherlight, packs small, layers over just about anything, and hits that sweet spot between cozy and breathable. Whether you’re battling overzealous airplane AC or adding a little polish to your sightseeing outfit, this wrap does it all — without taking up precious suitcase space.
Flip Flops That Mold To and Support Your Feet
These Reef Cushion Breeze Flip Flops are proof that toe freedom doesn’t have to mean foot misery. They mold to your arches, cushion every step, and actually stay on your feet without threatening to launch into the nearest baggage carousel. No blisters, no spinal shocks from wafer-thin soles — just soft, supportive bliss you can sprint in when your connecting gate is approximately 14 miles away.
Outfit #3: Nothing But Comfort for the Long Haul
For those marathon travel days (or worse, travel and a layover) when your only real goals are: 1) survive, 2) maybe sleep, and 3) arrive without regretting every clothing choice you made.
Style isn’t exactly the top priority when you’re bleary-eyed and facing down a customs line, but that doesn’t mean you have to look like a total disaster. Versatile, easy layers and fabrics that feel like pajamas—but pass as “presentable” in public—are the secret here. Bonus: every piece will still earn its keep later in your trip.
Lightweight Joggers to Keep it Loose
These Gym People Joggers are basically the socially acceptable version of pajama pants—soft, stretchy, and ridiculously comfortable, but polished enough that you won’t feel like a total airport gremlin. They’re perfect for a long-haul flight, a marathon layover, or a late-night dash to the hotel lobby for caffeine. Bonus: they pack down small and double as loungewear once you’ve reached your destination… or, ya know, “exercise clothes,” if you’re into that sort of thing.
This Sweatshirt is So Soft and Plush, It’s Like Being Wrapped in a Blanket All Day
On my overnight flight to Europe last year, this Trendy Queen Hoodie was the MVP. Instead of wrestling with the teensy-weensy airline blanket (which barely covers a knee, let alone your whole body), I tossed it over my legs and let this ultra-soft, plush wonder keep my upper half toasty. It’s the kind of hoodie that makes you feel like you’re in a cocoon of happiness, whether you’re in row 32C or wandering around a drafty terminal at 2 a.m.
Warm but Breathable Socks
Thick, soft, and cozy—but somehow still not sweaty. (My personal sock holy grail.) These wool-blend wonders keep your toes toasty, dry quickly if they get damp, and come in five-packs with options from classy neutrals to “these socks could start a conversation” brights. And at less than two bucks a pair, you can afford to lose one to the hotel laundry monster without shedding a tear.
A Slip On Shoe That Works All Day – And Doubles as a Slipper
The Cushionaire Hana Slip-On Clogs (complete with cork footbed and memory foam) are so comfy it’s almost suspicious. Unlike a lot of clogs, they stay on without that weird “toe clench” walk, and the cushy sole gives plenty of support for airport marathons. They’re the unicorn of travel shoes: easy to slip on for a mid-nap bathroom run, cozy enough for in-room lounging, and solid enough for exploring your destination without missing a step.
Bonus Round: My Favorite Pieces and Accessories
This is the stuff that separates the rookies from the road warriors—the multitaskers, the comfort-boosters, the “wow, that just saved my bacon” pieces. All field-tested by yours truly, all loved, and ready to make Future You weep with gratitude. Pack ‘em, wear ‘em, and bask in your own travel genius.
A Flowy Tank for Effortless Style and Comfort
The Geifa Summer Tank Top is a travel MVP—lightweight, soft, and just the right amount of flowy for everything from road trip naps to whirlwind city sightseeing. It drapes in all the right places, breathes like a champ when you’re dashing through a terminal, and hides any gelato-related consequences. Bonus: it comes in a ton of cute colors and prints, so you can stock up without feeling like you’re repeating outfits.
Leggings – With Pockets! – That Feel Like They’re Barely There
These CRZ Naked Feeling Yoga Pants may be a famous-brand dupe, but honestly? I just care that they’re the comfiest thing I own. The high waistband is perfectly snug (slimming without cutting off circulation), the fabric is silky-soft, and the pockets are deep enough to stash a truly irresponsible amount of nonsense—yes, including a water bottle. They’re my go-to for travel days, workouts, or just existing in maximum comfort.
Compression Socks That Keep You Cute and Circulating
After a marathon travel day (or two), my calves and ankles tend to merge into one alarming cankle situation—and that’s before we even get into the whole “blood clot risk” thing. These Bluemaple Copper Compression Socks are my secret weapon. They keep my legs feeling fresh, fight swelling, and come in fun patterns so you can wear them even when you’re not trapped in a pressurized tube. Function and fashion, baby.
Super Soft Leggings That That Move With You (and Your Snack Habits)
Felina’s Pocket Yoga Leggings are buttery soft and stretch like a dream—whether I’m feeling a little puffy from airport snacks or magically trim from all the sightseeing steps. They fit like a glove without that “gym only” vibe, making them perfect for curling up in an airplane seat or wandering a cobblestone street. And yes, the pockets are big enough for your phone and a granola bar.
The Ultimate Pashmina – The Travel Multi-Tool You Didn’t Know You Needed
It’s a blanket, a scarf, a wrap – and somehow still packs down smaller than your average paperback. Thin but surprisingly warm, it’s also handy for sun protection, modesty in temples, or dressing up a basic travel outfit. My Happy Luxe Shawl Wrap is hands-down the most-used thing in my carry-on, and now I can’t imagine traveling without it.
A Stylish Sneaker That’s Hands Free and Fabulous
When you’re sprinting to make a connection, juggling bags, and trying not to elbow a stranger in the face, you want a shoe that’s comfortable, supportive, and stays put. Bonus points if you can slip it on and off without folding yourself in half between airplane seats. Enter: the Kizik Sneaker. I was skeptical at first, but now I’m a believer — they’re comfy, they look sharp, and they’re a total game-changer for travel days.
Sneakers With All the Support and None of the Weight
My ride-or-die athletic shoe for travel days and endless urban wandering is the On Cloud 5 Sneaker. The arch support? Unparalleled. The weight? Practically nonexistent. The traction? Ready for cobblestones, slick subway stairs, or that random hiking trail you “accidentally” end up on. And with all the fun color combos, they look as good as they feel. Basically, they’re the whole package… in shoe form.
Sporty Sandals that Cradle Your Arches (and Still Pass the Cute Test)
With a yoga-mat cushioned sole that actually supports your arches, and a design that doesn’t scream “I live in a tent,” these Lancholy Sport Sandals are a traveler’s dream. Perfect for hot-weather adventures where you might get your feet wet, or for strolling through town in search of your next cute outfit. Active comfort and style—yes, you can have both.
My New Favorite Travel Purse – The Right Size, The Right Amount of Pockets, and a Monkey
I stumbled across my perfect bag at Marshall’s (as one does), and while I couldn’t find the exact one on Amazon, this Kipling Elysia Bag is basically its twin. It’s got straps that work perfectly as a shoulder or crossbody, one roomy main compartment, and just enough smaller pockets to keep me organized without going full “Mary Poppins bottomless tote.” It even swallows my big DSLR and lens without complaint. And the best part? The matching monkey keychain. Because I am, unapologetically, a sucker for a monkey.
Espadrilles That Give You Height Without the Wobble
I usually toss one pair of heels in my bag for those fancy dinners where flip flops just won’t cut it—but I’m also a giant spaz who wears heels about twice a year. Enter these Viscata Aiguafreda Espadrille Canvas Wedges: the wedge is sturdy enough to keep me from doing an unplanned face-plant, and the ankle strap makes sure my feet stay put instead of popping out all willy-nilly. Even better? They can swing fancy or casual depending on what you pair them with, so they earn their suitcase space.
This Visor Might Scream “Mom at Disney,” but It’s Saving My Sanity
My sister loves to mock me for it, but here’s the truth: I’m wildly photosensitive, I overheat easily, and both of those things turn me into a cranky goblin. I want my eyes shaded without turning my head into a sweat lodge, and this Andesieqy Sun Visor delivers. It keeps the sun out, the breeze in, and comes in wild colors and patterns that say, “Yes, I’m living my best chaos-grandma life—deal with it.”
Or a Winter Hat That’ll Keep You Warm — in Whatever Color Your Heart Desires
Allegedly, the fuzzy pom-pom on top of winter hats was invented to save people from bonking their heads on low ceilings back in ye olden days. True? False? Adorable either way.
This Page One Chunky Cable Knit Pompom Hat comes in a dizzying array of colors, from understated neutrals to “spot me in a snowstorm” brights. Cozy, cute, and cheap enough to grab one in every shade that matches your travel wardrobe.
A “Sleeping Bra” So Comfortable, You Might Forget You’re Wearing It
I’m almost at the stage of life where I say, “bras be damned,” and mean it. But when I’m slogging through airports with my carry-ons and dignity barely intact, a little support is nice.
This Jeminay Wireless Sleeping Bra is soft enough to forget it’s there, yet still keeps my melons from making a break for it. Truly, the best of both worlds.
A Wire Free Bra That Supports the Girls Without Poking You in the Ribs
If you want something a bit more traditional than a sleeping bra — one you can wear under a tank top without it announcing itself to the world — the Floatley Comfort Wirefree Seamless Bra is your gal. It’s buttery soft, gives just enough shape to look put together, and won’t have you waking from your in-transit nap wondering if you’ve punctured a lung.
“Safety Shorts” That Save Your Thighs and Your Sanity
Even at my slimmest, my thighs have always been best friends — they just insist on hanging out together. In hot weather, that means chafe city. These Wirapa Cotton Boy Shorts keep the peace, letting me wear skirts and dresses without the dreaded burn. As a bonus, they’re seamless, so no panty lines crashing the outfit party. Hazah!
Everyday Athletic Socks That Won’t Quit (or Slip)
Few travel tragedies compare to a sock sliding off your heel and bunching up in your shoe. These Saucony Rundry Performance Athletic Socks save me from that particular circle of hell — they stay put, add just the right amount of cushion, and feel so good I forget I’m even wearing them. Comfort that lasts through cobblestones, airport sprints, and the occasional rainstorm.
Want more of my tried-and-tested travel must-haves?
I’ve road-tested, flight-tested, and occasionally disaster-tested more gear than I can count — and I’ve rounded up all the winners. Check out my other Travel Essentials pages below!