If you follow me on Instagram, you know I am a big fan of all things fall, including fall travel and fall fashion. In light of the changing season, I thought I’d share some of what I think are the best fall travel outfits. Whether you’re heading out for a work trip, a family getaway, or a fun girls trip, I’ve got outfit ideas that will keep you feeling comfy and looking chic. From cozy sweaters and stylish coats to versatile sneakers, these looks will have you covered for any occasion. So stay tuned for more fall travel outfit inspo!

Best Fall Travel Outfits
Travel in the fall can be overwhelming and luggage can be bulky if you are traveling to colder places. You may need to prepare for rainy and colder days of the season, so it’s important to really think about your outfits when traveling. If planned right, you will not only look good, but feel comfortable when traveling.
Fall Travel Capsule
There are a few items I can’t live without when traveling. Aside from the classic rain jacket and comfortable shoes, if you looking for more capsule wardrobes, check out my fall capsule wardrobe:
- Lululemon Align Leggings
- Black Faux Leather Leggings
- Golden Goose Sneakers
- Trench Coat
- Wool Coat
- Hooded Sweatshirt
- Scarf
- Black Blazer
- Agolde Jeans
- Beanie or Baseball Cap
Knit Dress Outfit
I’m loving styling a comfortable knit dress for my fall trip, especially when it’s paired with my favorite tan Adidas Sambas. Layering a denim jacket over the dress gives the outfit a cozy feel, perfect for the fall color palette. With this look, you’re all set for a stylish and practical adventure!

Leggings and Blazer Outfits
If you want to look put together but still stay comfortable while traveling, my go-to is a leggings and blazer outfit. I love opting for my favorite pair of black leggings, then layering a cozy sweater or tee underneath. To finish the look, I add a blazer, either keeping it casual with a hooded one or elevating the vibe with a faux fur blazer. For shoes, I’m loving my Adidas Sambas, which are perfect for tying the outfit together. Be sure to check out my review on them here!


Shorts Set Outfit
I love a matching sweat shorts set with a sweater and shorts combo because it’s so easy to style while traveling. The set is perfect for a laid-back yet put-together look, especially for a fall trip when the weather is in transition. Just add your favorite white t-shirt, neutral sneakers, a hat, and a bag, and you’re all set! The look is cozy yet chic, and the neutral color palette makes it versatile for different outfits and occasions. Plus, it works well if you want to swap the shorts for wide leg jeans when the weather cools down!

Sweats Set and Sneakers Outfits
Similarly to a shorts set, as the weather gets cooler, I love opting for a matching sweatpants set. It’s so easy to style and looks effortlessly chic. Go for a matching pants and top look in a neutral color palette like white, gray, or black. To finish the outfit, accessorize with a denim jacket, a tote bag, and your favorite sneakers. This look is perfect for a fall trip and offers that cozy yet stylish vibe that’s ideal for transitioning into cooler weather.



Black Trousers and Button Down Shirt Outfit
If you’re traveling for work or an occasion where you want to look chic but stay comfy, opt for a black trousers and button-down top outfit. It’s such a polished yet comfortable look, perfect for hopping off the plane and heading straight into the office. Pair the outfit with sneakers for the travel portion, then swap them for heels once you arrive. Be sure to check out my post here for more travel outfit ideas for work.

Blue Jeans Outfits
Blue jeans are so timeless. They’re comfortable, easy to style, and always look cute. For a fall trip, I love opting for an easy blue jeans outfit by pairing them with a classic long sleeve, short sleeve tee, or even a cozy sweater. Depending on the temperature, you can layer with a jacket for that perfect fall vibe. Finish the look with your favorite bag, and you’re all set for a chic yet effortless travel outfit. Blue jeans are the ultimate go-to for any fall color palette, and they also even work great with wide leg styles for added comfort and flair! Don’t forget to check out my Denim Fit Guide to find your perfect pair of jeans!



Black Dress and Sneakers Outfit
If you’re traveling to a special event and want to look chic when you arrive, a black dress and white sneakers outfit is the perfect option. Not only is it comfortable for travel, but it also looks effortlessly stylish. For a fall trip, layer your black leather jacket over the dress to add a bit of edge and warmth, then finish off the look with white sneakers. It’s such an easy yet polished outfit. When you get to your event, you can simply swap the sneakers for heels for an instant upgrade. If you’re looking for more white sneakers to wear with dresses, check out my post here.

Monochrome Leggings Outfits
Leggings are perfect for fall traveling because they’re so comfy and easy to style. To keep your leggings look chic, I love opting for a monochrome or tonal outfit. Choose the same color or colors in a similar palette, like a matching green set, which I’m absolutely loving right now. It creates a sleek, put-together vibe while still being super comfortable. Then, pair your leggings with sneakers and your favorite tote bag for a comfy yet cute outfit that’s perfect for a fall trip. You’ll look effortlessly stylish while feeling cozy and ready for whatever the day brings!


Black Skirt and Adidas Sambas Outfit
If you want to feel comfy but still look elevated for your fall travel, opt for a black skirt outfit. Pair it with a classic white long sleeve for a chic, balanced look. Add your favorite sneakers to keep it casual and comfortable, perfect for long days on the go. To elevate the look or stay warm, layer on your favorite fall coat or cozy sweater. This outfit fits seamlessly into a fall color palette and is ideal for a stylish yet practical travel look.

Black Jeans and Adidas Sambas Outfits
For a twist on the classic blue jeans look for fall, opt for black jeans, they’re so chic and incredibly easy to style. I love wearing mine with a classic t-shirt or a half-zip sweater for a cozy yet polished vibe. To complete the outfit, layer on your favorite coat for extra warmth. For footwear, sneakers are the perfect choice, and I’m especially loving Adidas Sambas right now. They keep the look comfy while adding a stylish, sporty edge, making this outfit ideal for fall travel!






Graphic Sweatshirt with Black Jeans or A Pair of Black Leggings

Graphic tops, like a graphic sweatshirt and graphic t-shirt, is one of the biggest trends this year. I love packing mine for travel. Here, I layered it with a long sleeve turtleneck underneath for extra warmth and my favorite black straight-leg jean and golden goose sneakers.
Flannel Shirt or Shacket Outfit

Shackets and flannels have been one of the best, most popular, and longest-lasting trends for as long as I can remember. Definitely consider adding at least one of these clothing pieces to your travel packing list.
Casual Airplane Outfits for Travel

Outfit Details

Outfit Details



Abercrombie Faux Leather Jacket | Alo Legging | Amazon Sunglasses | Nike Sneakers
Sweatshirt & Jogger Outfit
Easy To Pack Travel Outfits that you can Plan to Wear Other Ways
Cozy Sweater & Pair of Black Faux Leather Leggings



Commando Faux Leather Leggings | Amazon Sunglasses | Cropped Grey Sweater | Abercrombie Faux Leather Jacket
Brown Wool Coat & Faux Leather Leggings Travel Outfit

Mango Wool Coat | Commando Faux Leather Legging | Chloe Lace Sneakers
Trench Coat & Pair of Black Faux Leather Leggings Outfit

Burberry Trench Coat | Commando Faux Leather Leggings | Black Stocking | Rag & Bone Winter Boots
Snakeskin or Leopard Print Faux Leather Leggings & Winter Fall Boot

Sightseeing Travel Outfits
Leather Jacket Travel Outfit

Outfit Details

Outfit Details
A leather jacket is my favorite fall staple and if I’m traveling it’s coming with me however, it can be bulky in your suitcase so I recommend wearing it on the plane (or grabbing some efficient packing cubes). It’s one item that can be worn casually for the day of sightseeing or over a dress for a night out. Plus, it can be mixed and matched with nearly any color palette, which means you can pack fewer jackets.
Cozy Sweater Travel Outfit

Outfit Details
A cozy sweater is always a must for me when traveling. You can style it casual with sneakers and easily pack a slip skirt to dress it up for an evening dinner. Mix and match with various pairs of straight or wide-leg jeans, or even some black pants.
Hooded Blazer & Boyfriend Jeans Outfit | Black Blazer & Ankle Boots Travel Outfit


Adding a blazer to your classic staples is the perfect travel look especially if you get off the plane and head straight to a meeting or lunch or cocktail hour. It is sophicasted and chic while also being comfortable. A good blazer can take your outfit from drab to fab, and at no extra cost.
Black Skinny Jeans & Cashmere Sweater Outfit

A cashmere sweater is one of the best travel essentials as they are lightweight and easy to pack while also keeping you warm on colder winter days. A good cashmere sweater is a travel clothing must-have.
Don’t forget to pin to save for later!

Be sure to check out my latest posts here!
- 60 Shoes to Wear With Maxi Dress
- When to Start Using Retinol
- How to Exfoliate Scalp
- Greece Outfit Ideas for Summer Travel
- 30 Bodysuit Outfit Ideas
Please feel free to email me at thegraydetails@gmail.com if you have any questions! I’m always happy to help with styling or picking out a specific outfit for an event! Have an amazing day!!!
You can also download the free LIKETOKNOW.IT app and follow me HERE.
STAY IN THE KNOW: Don’t forget to sign up for my exclusive Newsletter for STYLE TIPS, SALE ALERTS, AND MUCH MORE!
As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda