Fall Travel Outfits That Look Chic and Comfortable

Every time the season changes, I get excited to update my wardrobe and see what’s coming next. Fall is one of my favorite times to layer up in cozy pieces and chic looks, especially with a couple of trips planned. If you’re traveling this season too, these fall travel outfits are perfect for staying comfortable but still looking pulled together wherever you go.

Fall Travel Capsule Wardrobe Essentials

Building a fall travel capsule wardrobe is all about keeping things simple, versatile, and stylish. You don’t need to overpack; just a handful of pieces that mix and match will give you plenty of interchangeable outfits for any trip. These are the fall travel essentials I always rely on, the kind of staples that make getting dressed on the go easy while still feeling put together. Here are some of my go-to fall travel essentials:

1- Cozy Fall Jackets

Cozy fall jackets are one of my favorite things to pull out this time of year because they make every outfit feel effortless. They’re warm without being bulky, easy to layer over anything, and instantly make you look more put together. I love that you can pair it with leggings and sneakers for travel days, or dress it up with jeans and ankle boots for dinner. It’s that one piece in your suitcase that keeps you comfortable but still stylish, no matter where you’re going.

2- Comfy and Chic Puffers

I love that they’re lightweight and easy to pack; you can roll one up in your suitcase or even carry it on the plane without it taking up all your space. A good puffer always looks polished, works with just about any outfit, and gives you that extra layer of comfort when the weather cools down. It’s practical but still stylish, and that’s exactly why it’s one of my go-to pieces for fall travel.

3- Neutral Sweater

A neutral sweater is honestly one of the easiest things to throw in your suitcase because it works with literally everything. I’m talking about those simple colors—like beige, cream, gray, or black—that can instantly look casual with leggings and sneakers during the day, but then feel a little more polished at night with jeans, ankle boots, and maybe a scarf or a leather jacket on top. It doesn’t take up much space, it layers perfectly, and it’s one of those pieces you’ll end up wearing over and over again without feeling like you’re repeating the same outfit.

4- Leggings or Joggers

Leggings or joggers are a total must for me when I’m traveling, as they’re incredibly comfortable for flights and long days. You can sit for hours on a plane, run through the airport, or explore a new city without feeling restricted. I love that you can style them in so many ways too—throw on sneakers and a hoodie for a laid-back look, or pair them with a long coat and boots to instantly look more put-together. They’re easy to pack, don’t wrinkle, and honestly, I always end up reaching for them more than anything else.

5- Chic Sneakers

I think sneakers are a total must-have for fall travel because they’re comfortable enough for long days but still look chic. You can opt for a classic flat sneaker, a platform style, or something sleek and minimalist that pairs well with just about everything in your suitcase. The best part is their versatility. Pair them with leggings and a trench for the airport, or wear them with jeans and a sweater while exploring a new city. They keep you comfortable for all the walking but still make you feel put together.

6- Ankle Boots

I love ankle boots because they’re incredibly comfortable and easy to pack, even in a small carry-on. They work with everything, from jeans and leggings to a cute fall dress, and instantly make your outfit look a little more polished. I like bringing a neutral pair that I can wear on repeat without feeling like I’m wearing the same thing every day. They don’t take up much space, and honestly, they’re one of those staples I always end up wearing the most on trips.

7-Trench Coat or Leather Jacket

I always bring either a trench coat or a leather jacket in the fall because they instantly pull an outfit together without trying too hard. A trench is lightweight, super chic, and perfect for layering over sweaters or even joggers when you want to look a little more polished. A leather jacket, on the other hand, gives everything that incredible, effortless vibe and works with literally anything—jeans, dresses, or leggings. Both are easy to pack, and honestly, just having one of them in your suitcase makes your whole fall travel wardrobe feel elevated.

8-Scarf

I always throw a scarf into my bag because it’s lightweight, cozy, and takes up barely any space, but it makes such a difference when you’re traveling. You can use it on a chilly plane, wrap it around your shoulders at night, or add it to a simple outfit to make it look more stylish. I love how a scarf can completely change the vibe of your look without requiring you to pack a bunch of extra pieces.

9- Simple Fall Travel Dresses

I love packing a couple of simple fall travel dresses because they’re so easy to throw on and instantly feel put together. You can layer them with a leather jacket, trench, or even just a cozy cardigan, and they work just as well with sneakers during the day as they do with ankle boots at night. They don’t wrinkle easily, they take up hardly any space in your suitcase, and they give you that polished look without any effort.

10- Crossbody Bag

I always bring a crossbody bag when I travel in the fall because it just makes life so much easier. It keeps your hands free for coffee, passports, or wrangling kids through the airport, and it feels so much safer than carrying something on your shoulder that can slip off. I love that you can fit all the essentials—phone, wallet, lip balm, sunglasses—without it being bulky, and it goes with literally any outfit. A neutral crossbody works with everything you pack, so you don’t need to bring more than one.

11- Denim Jacket

A denim jacket is one of the easiest layers to pack for fall travel. It works with just about everything: dresses, leggings, joggers, or even over a cozy sweater on chilly days. Lightweight yet stylish, it’s the kind of piece you can wear during the day while exploring and still wear for a casual dinner at night. The best part is its versatility; you can dress it up or down, and it always feels in place.

Best Fall Travel Destinations | Picture-Perfect Places to Visit

These are some of my top favorite places to see in the fall, and each one turns into a postcard the moment the leaves start changing:

Vermont – Known for its rolling hills, charming inns, and the brightest foliage you’ll ever see. Everywhere you look feels straight out of a painting.
Boston, Massachusetts – A mix of history and charm, with tree-lined streets and parks that glow in shades of gold. The perfect city for crisp fall walks.
New York City – Central Park in the fall is breathtaking, and the whole city feels alive again. There’s nothing like exploring NYC in cozy layers.
Toronto, Canada – A vibrant city surrounded by beautiful parks and waterfront views. The mix of urban energy and fall colors is hard to beat.
Vancouver, Canada – With mountains, water, and fiery leaves all around, it’s one of the prettiest fall backdrops you could ask for.
Montreal, Canada – Feels like a little slice of Europe with cobblestone streets, great food, and trees showing off their best colors.
Napa Valley, California – The vineyards turn stunning shades of red and gold during harvest season, making it the perfect fall getaway.
Aspen, Colorado – The golden aspen trees against the mountain views are pure magic. It’s cozy, scenic, and unbelievably beautiful in autumn.
Quebec City, Canada – Old-world charm with narrow streets, cozy cafés, and brilliant foliage. It’s basically a fairytale town in the fall.
Finger Lakes, New York – Known for lakeside views, wineries, and incredible fall foliage. A peaceful spot to enjoy the season.

Final Thoughts

Fall is such a fun time to pack a bag and head somewhere new, whether it’s a quick weekend trip or a longer getaway. It’s the season where you actually look forward to pulling out cozy layers and mixing in a few chic staples that make traveling easier. When you’ve got the right fall travel outfits, you don’t have to stress about what to wear; you’ll feel comfortable the whole time and still look cute in every photo along the way.

Love,

Sherry XOXO