Cute and Comfortable Fall Travel Outfits

Good morning and happy Friday! 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.

Ten of The Best Fall Travel Outfits For Your Next Trip

I just took my first flight and first longhaul flight with my baby to London for a little fall getaway. 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 has turned out really well so far!

Longhaul flights can be tricky when you’re picking out what to wear. I really prioritize comfort, but I still like to feel like I’m not just wearing pajamas. So, I felt inspired to write a blog post about cute travel outfits for the fall season – things you can wear on the plane and then a couple of outfits that are easy to pack and wear right away when you land or otherwise arrive at your destination.

Comfortable Fall Travel Outfit For Flying

I’m in love with this travel outfit. I can’t even describe to you how soft everything is! Both of these pieces are like wearing a cloud, ha! They’re seriously so comfortable, and these colors are all perfect for fall. While I love places like Alo and Lululemon for comfortable looks and exercise clothes, I was excited to find something different and new to me!

Cute and Comfortable Fall Travel Outfits

This store was an absolute dream to visit! Check out my London highlight on my Instagram to see what I mean. My exact pants are linked below, and my exact top is linked below in black. It’s sold out online in the color I’m wearing, but I would also wear it with black or with the other two tops I linked as they are the same color as my pants.

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Soft Pieces to Mix & Match

I tried my top with my jeans to make sure I could wear it in more than one way. 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 because they didn’t have the right size for me in the pants, but click here to see what they look like on as I’ve linked some of them below. There are tons of colors on the website, and you basically pair anything together – or with jeans when you land!

Matching Sets 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 and they’re so easy to plan to wear. 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.

I love the look of these three matching sets. The color options are so good! The cuff on the pants adds a nice touch to otherwise standard looking sweatpants. You could also pair these with ballet flats if you wanted to elevate your look, but I like them best with sneakers. Since the top is long sleeve, I would layer it with a short sleeve top or tank top under it in case you get warm.

Cute and Comfortable Fall Travel Outfits

Tunic Top 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 love a cozy top and leggings with socks and sneakers. I wore this exact outfit on my flight over to London, and it was perfect. This is the type of look you probably already have in your closet! If you don’t want to wear a sweater, you could also go for an oversize button-up like this one.

I also took this coat with me on the plane because I knew it would be colder in London than DC. It’s the first time I’ve traveled with it, but it didn’t lose its shape and I didn’t get hot wearing it around the airport.

The outfit below is a great option for a short flight when you just need your suitcase and a personal bag. I own this hat in black and wear it often for travel.

Tunic Top and Leggings

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. I absolutely love this Free People top because it’s long enough to cover your bum when you’re wearing leggings, but it tucks into jeans or a skirt too.

fall travel outfit ideas

The same goes for the outfit idea below. Trade your joggers for jeans! You could also wear these joggers around for quite a bit after your travel because they look very nice in person. They’re the same pair I’m wearing in the first photo of this post.

Comfortable travel outfit for fall

Okay, last but not least, I always need a carry-on or a travel bag of some sort that is not an actual suitcase. I love Louis Vuitton soft luggage bags for carry-on bags. They are seriously so durable, and mine has not shown any wear despite being shoved into cars and under plane seats. But, I also use my Longchamp bag. The key for me is having a zipper. I can’t stand when a travel bag doesn’t have a zipper!

Comfortable and Stylish Sweater Set

This outfit is another great pick for a long day of travel. I like that it matches so it’s a little bit more elevated than a jogger look. You could easily wear a long coat over this look and head out once you arrive. Personally, I would probably wear a white baseball cap with this look, but I thought the pink and lilac were fun!

Stylish Sweater Set

Easy Fall Travel Outfit For When You Arrive: Sweater and Jeans

I don’t really wear jeans to fly, but they’re great to have for fall weather for when you land! This isn’t a groundbreaking outfit! A cozy cashmere sweater, wide leg jeans, and ankle boots were the perfect daytime outfit for walking around. This look goes with any type of jeans, of course. I also like to wear this with skinny jeans or straight leg jeans. You can read more about my jeans in this blog post. Anyway, I like this outfit because it’s easy and you can just grab it from your suitcase to throw on.

I love this sweater – it isn’t available in my exact color anymore, but it comes in a gorgeous brown and several other options.

Easy Fall Travel Outfit sweater and jeans

Stress Free Fall Travel Outfit For Dinner: Sweater Dress

A sweater dress is another option that’s great to pack because they’re perfect for fall and they’re also easy to wear once you’ve reached your destination. If you have dinner plans the day you arrive or even close to when you arrive, you can throw this on with cute boots and be on your way! I just bought this one for family photos in size US 4. Click here to see another one I tried on and keep thinking about!

If you’re looking for other pieces for the fall, check out my capsule wardrobe blog post and my fall closet staples 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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