Cute and Comfortable Fall Travel Outfits

Good morning! Fall is one of my favorite times of the year for travel, especially for a trip to a city. It’s not too hot to walk all around and it’s nice to avoid the rush of summer travel. Plus, there are so many places in the US and abroad that are especially beautiful this time of the year. So, today’s post is all about what you might want in a fall travel wardrobe. If you travel frequently, maybe you want to prioritize a color palette that you can create a travel capsule wardrobe from. Or, you can have one go-to outfit for travel! I’ve included options for both below.

Ten of The Best Fall Travel Outfits For Your Next Trip

Last year this time I had just taken my first flight and first long haul flight with my baby to London for a fall escape. I was so nervous leading up to the trip. As someone who loves to travel, that is not normally how I operate when it comes to packing and getting ready. But, it was all perfectly fine! I realized that, as a new mom, I wasn’t as focused on what I’d be wearing on the plane. So, it was nice to have an outft that I could easily pull together for myself once everything was packed for baby.

It can be tricky to know what to wear on a long haul flight whether you’re traveling solo or traveling with your entire family. I really prioritize comfort, but I don’t want to feel like I’m wearing pajamas. So, I felt inspired to write a blog post about cute travel outfits for the fall season, whether you’re getting on a plane or in the car.

Comfortable Fall Travel Outfit For Flying

The jogger pants and pullover I’m wearing below are two of the softest pieces I’ve ever felt, which made them perfect for travel. I can’t even describe to you how soft everything is! It’s like wearing a cloud. They’re seriously so comfortable, and these colors are all perfect for fall.

Cute and Comfortable Fall Travel Outfits

I use affiliate links throughout this blog post, which means I might make a commission if you use my link and then make a purchase. This commission comes at no cost to you.

You can shop my exact top here and my pants here. I’m wearing size small in both for reference. They come in tons of different colors. This store was an absolute dream to visit! Check out my London highlight on my Instagram (LDN 23) to see what I mean.

Elevated Loungewear Pieces to Mix & Match

I tried the top I’m wearing above with jeans to make sure I could wear it in more than one way. The outfit below is also Varley. And, to that end, this company’s gorgeous pieces can mix and match in so many different ways. I also tried on a few other pieces that I loved. I didn’t buy these two pieces (top here and pants here) because they didn’t have the right size for me in the pants, but I really love this color. There are tons of colors on the website, and you basically pair anything together – or with jeans when you land!

Elevated Loungewear Pieces to Mix & Match

A Matching Set for Long Travel Days

Matching sets are one of my favorite things to wear for any type of travel, but especially for a long drive or a long flight. In fact, matching sets are perfect for a few reasons: they’re comfortable, they’re so easy to plan to wear, and they look nicer than regular pajamas. If you’re anything like me, you don’t want to have to think about putting an outfit together when you’re checking your packing list at the last minute.

This matching set is super cute. I love the neutral tones. The sweatpants look perfectly cozy. I would wear a thin t-shirt or tank top underneath the sweater in case you get warm. Pair with sneakers and cozy cashmere socks! This type of set is also easy to layer under a rain jacket, trench coat (this is the one I own too), or winter coat if you need one!

cozy matching set for travel

Oversized Cashmere Sweater and Leggings: Perfect for the Airport or Car

This outfit idea is one of my go-to outfits for travel of any kind, whether you’re in a car or getting on a plane. I wore this outfit in different colors on my flight over to London, and it was perfect. There’s something super comfortable about an oversized sweater, especially if it’s cashmere. Size down one size as this sweater is truly an oversize cut. I really love these leggings in navy. While I wore them in brown on my flight last year, I recently picked them up for myself in navy! I’m also linking this pair of cashmere socks that I wear every fall and winter. I would pull the socks over the leggings to be extra cozy since the socks are cashmere.

I took this coat with me on the plane because I knew it would be colder in London than DC. It doesn’t lose its shape, and I don’t get hot wearing it around the airport even though it’s mostly made of wool. I linked the cream option below to go with the outfit I styled. I wear this coat in brown so much that I’m considering it in another color. You could also wear this outfit under a trench coat or a rain jacket like the two I linked above.

Oversized Cashmere Sweater and Leggings

I love this hat in this sand dollar color option. It’s perfect for this outfit. I own it in black and wear it all the time – it feels like denim.

Elevated, Chic Travel Outfit And You Won’t Need To Change

If you’re looking for jeans that are comfortable enough to travel in and still look ready for the day, this outfit is for you. The elastic waistband, loose fit, and lightweight cotton is the perfect recipe for comfort! You won’t be too hot or too cold in a short sleeve cashmere top. This wrap coat gives a chic feeling instead of a utilitarian vibe in this cream color, and these shoes are just gorgeous. You could also wear a boucle hat or this denim hat if you want to cover your hair after a long trip.

Cute and Comfortable Fall Travel Outfits

I love this cream color palette, but you could also style this with green and tan – see below!

Flare Crop Leggings With Oversize Half Zip

These flare leggings are cropped in a way that look like they will be the perfect length! One of my issues with flares is they tend to drag the floor or are close to it. I styled these pants with a fitted t-shirt that I would plan to wear under the half zip for comfort. This is the type of outfit I would wear for a long car ride to family’s house, where you’re going to get out of the car and just want to be comfortable.

Cute and Comfortable Fall Travel Outfits

Easy to Change From Plane for Touring Around

This outfit is comfortable for travel, but if you throw on blue or black denim once you arrive, it’s just as good for sightseeing, lunch, or a casual dinner shortly after you arrive. I recommend this pair of jeans because they’re really comfortable. I size up one size for a looser fit and because I carry a little bit of weight in my stomach. So, they’re the perfect type of jean to wear after a long trip. I absolutely love the Free People top I linked because it’s long enough to cover your bum when you’re wearing leggings, but it tucks into jeans or a skirt too. Be sure to size down one size because it runs big. If you’re pregnant, take your normal size! I wore this top throughout pregnancy. You can see it on me here and here in white.

A Travel Outfit You Can Elevate Or Keep As Is When You Land

This look is similar in utility to the one above because you can either wear these joggers or elevate your look with jeans. The joggers are the same pair I’m wearing in the first photo of this post, but I think black makes them look a little more elevated! This cardigan is super oversized, and it feels like it will be warm. So, I would definitely wear a t-shirt under it in case you get warm throughout your trip!

Cute and Comfortable Fall Travel Outfits

Satin Pants You Can Wear Right Off The Plane, Train, Or Car

These satin pants should definitely be a go-to for travel because they’re a pull on pant and clearly very flowy. This material is easy to style because you can wear it with other textures, whether that’s wool, cashmere, or a cotton top. I paired it with a lightweight, thin wool-blend layering top that you can wear under this relaxed fit lady jacket cardigan. I own it in blue and white, and I love it. It runs true to size. I do not recommend drying it – I let mine air dry. Click here if you’d like to see how it looks on me!

Cute and Comfortable Fall Travel Outfits

Travel Outfit To Wear From The Plane Straight To Work

If you’re traveling for work, I love this outfit if you need to go straight from the plane to the office. This cashmere cardigan with a matching tank top is comfortable enough to travel in but definitely work appropriate.

If you’re looking for other pieces for the fall, check out my capsule wardrobe blog post. There are several pieces you can pull from those looks for travel outfits as well. A button-up, layering shirt, and sweater coat are also travel essentials and work in so many other ways in your closet! Those are all good options for fall travel looks. I hope you have a perfect fall trip!

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