Whether it’s a night journey, a train trip, or a weekend getaway, one thing is certain: our travel outfits should keep us comfortable for long periods of time and reflect our style. So how do we choose the right travel outfit? Will the outfit we choose withstand a long journey, and will we still feel stylish when we arrive at our destination?
Here, I’m sharing 8 stylish travel outfit ideas that will withstand long journeys and keep you comfortable in chaotic areas like train stations.
1. The Classic: Leggings + Oversized Sweater + Sneakers
This combo is a travel classic for a reason. Black high-waisted leggings paired with a cozy oversized knit or sweatshirt is effortlessly cool. Add a pair of sleek white sneakers and a crossbody bag, and you’ve got comfort and style in one.
Bonus: Swap sneakers for chunky boots if you’re landing somewhere colder.
2. Matching Lounge Set + Trench Coat
A monochrome lounge set in soft cotton or knit fabric is the modern traveler’s uniform. Toss on a lightweight trench or longline coat, and your look instantly transforms from “couch ready” to “airport runway.” It’s the definition of off-duty model vibes.
Style tip: Neutral tones like camel, grey, or beige keep the outfit feeling elevated.
3. Maxi Dress + Denim Jacket + Slip-On Flats
For warmer destinations, a flowy maxi dress is your best friend. It’s breezy, stylish, and perfect for those unpredictable airplane temperatures. Throw on a denim jacket for warmth and structure. Slip-on loafers or mules complete the look with ease.
Bonus: Maxi dresses can double as dinner outfits once you arrive.
4. Paperbag Waist Trousers + Basic Tee + Cardigan
Paperbag or wide-leg trousers are a step up from leggings but just as comfy. Pair them with a tucked-in tee and a long cardigan or wrap. This is a chic, minimalist outfit that’s made for travelers who like a bit of polish without the fuss.
Add-ons: A slim belt and structured tote elevate this even further.
5. Bike Shorts + Oversized Shirt + Baseball Cap
Athleisure is perfect for early morning flights or road trips. Bike shorts keep things breezy, while a loose, oversized button-up shirt adds contrast and coverage. Finish the look with a baseball cap and your favorite sneakers.
Pro tip: Opt for a shirt with a pocket to stash boarding passes or earbuds.
6. Denim-on-Denim
Don’t fear the Canadian tuxedo. A light-wash denim jacket over black or dark jeans (or even denim joggers) can be surprisingly stylish. Break up the texture with a plain white tank or ribbed top.
Make it pop: Add a bold scarf or red lip for a fashionable twist.
7. Tunic Top + Leggings + Ankle Boots
A long tunic or shirt dress layered over leggings is an effortlessly put-together look that also keeps you cozy. Ankle boots with a slight heel offer comfort and a touch of sophistication—ideal if you’re heading straight to a meeting or dinner after landing.
Travel hack: Choose a wrinkle-free fabric for the tunic—like modal or jersey.
8. Sweater Dress + Belt Bag + Tall Boots
Need something versatile? A soft knit sweater dress paired with tall flat boots and a belt bag (worn crossbody) gives you an effortlessly cool silhouette. The best part? It’s one-piece dressing—no need to coordinate separates when you’re short on time.
Style note: Go for midi-length to keep warm on chilly flights.
Final Packing Tips:
- Layer smartly: Airplanes can be freezing. Always bring a wrap, cardigan, or oversized scarf.
- Stick to neutrals: They’re easier to mix and match.
- Pick pieces that pack well: Avoid anything that wrinkles easily or takes up too much space.
- Accessorize minimally: Sunglasses, a tote, and one statement piece are all you need.
Traveling doesn’t mean sacrificing style. With a few versatile pieces and thoughtful pairings, you can look effortlessly chic from check-in to check-out.
