12 Amazon Fall Travel Clothing Picks September 2025

As far as I’m concerned, September 1 is the official start of fall. Once the first hint of a chill hits the air, I switch over my summer wardrobe in favor of cozy knits and flowy maxi skirts, all of which are my preferred essentials for travel during the cooler months, as well. A quick audit of my dresser drawers revealed I was in dire need of some fresh pieces to sport during my upcoming adventures, so I turned to Amazon for inspiration and was not disappointed.

From the perfect oversized cardigan (with pockets!) to a denim shacket I guarantee will be the highlight of every fall vacation photo, I’ve rounded up the 12 best seasonal fashion picks available at Amazon for under $50. They’ll prepare you for city excursions and rural outings alike, not to mention they’re thoughtfully selected to occupy minimal space in your suitcase.

Best Deals Overall

Lillusory Oversized Knit Cardigan

As soon as September hits, my cardigan collection is the first thing I bring to the front of my closet. Since I’m always a sucker for a new addition, I’m eyeing this drapey knit cardigan for my fall travels—and right now it’s on sale for 42 percent off. The sweater’s deep pockets are the perfect place to store my in-flight snacks, plus it’s lightweight enough that it won’t take up too much space in my personal item when I’m not wearing it. 

Anrabess 2-piece Lounge Set

As someone who exclusively wears loungewear during travel days, I’ve been on the lookout for a matching set that will elevate my look without impacting my comfort. Enter: the Travel + Leisure editor-approved Anrabess Lounge Set. This buttery-soft duo features a pullover half-zip sweatshirt and a pair of elastic waistband sweatpants that look great worn together or separately. It boasts a more fitted finish than other sets, resulting in a more flattering look altogether. Plus, it comes in 21 beautiful colors that are all fit for the new season. 

Plnotme Jean Tie-front Denim Shacket

Shacket season is finally here, and the moment I laid eyes on this denim tie-front layer, I knew it was exactly what my travel wardrobe had been missing. Since the weather tends to fluctuate in the early weeks of fall, this will be a great piece to throw on over a tank top in the mornings while sightseeing, but it won’t be a burden to carry once it warms up, either. The boxy fit will easily layer without feeling too bulky, and the front is fitted with functional pockets for my phone, headphones, and even some extra snacks. In fact, shoppers have even likened it to higher-end lookalikes, so it’s well worth the $35 price tag.

Dream Pairs Chunky Heeled Loafers

Loafers are one of the most timeless fall footwear styles, and after spotting this chunky pair on sale for $34, I’m adding them to my shopping cart for my next trip. The convenient pull-on design and soft leather exteriors are both sensible and comfortable, and shoppers have confirmed that they’re “great for lots of walking and standing for long periods of time without pain.” A simple black pair will look great with everything from a pair of wide-leg jeans to a plaid mini skirt, and the nearly 2-inch heel adds just a bit of height without being difficult to walk in. 

Ekouaer Active Performance Skort

My goal with my fall travel wardrobe is to build a collection of pieces that are both stylish and functional, and this athletic skort falls well within those parameters—plus, it’ll look great in photos. Built-in shorts provide ample coverage so I’m free to frolick down the streets of my destination without feeling exposed, and the stretchy polyester and spandex blend won’t feel restrictive. I’ll be able to dress it up with loafers or down with a simple pair of sneakers, and while it’s as comfy as a pair of lounge pants, it’s far more fashionable. 

Dokotoo Casual Smocked Dress

I’ve never been a fan of tight, form-fitting dresses, so this babydoll-style tunic is a much more favorable pick for my fall travels—especially now that it’s on sale for just $30. The flouncy, loose skirt and billowing sleeves add feminine charm to this relatively plain piece, and with the right accessories (and perhaps a pair of knee-high boots), it’ll surely become a go-to whether I’m enjoying a weekend at home with my family in New Hampshire or a New York City excursion.

Shewin Casual Long-sleeve Sweater

I keep a lightweight sweater in my bag at all times throughout the end of summer and early fall, and the dainty crochet detailing on this pullover piece sets it apart from others in my collection—as does the $19 price tag. Since the fit is relatively oversized, I’ll be able to throw it on over a dress if I get chilly, or tuck it into a maxi skirt for a more carefree look. And with so many gorgeous neutrals to choose from, I may be tempted to add more than one shade to my cart.

Dlooda Flare Leggings

As an avid shorts hater, I’ve been looking forward to the moment that I could break out my leggings for months now—and I’m rewarding my patience with a new pair complete with a flattering flare fit and crossover detailing at the waist. I prefer to stay active during my travels, so these pants will be an asset during sightseeing excursions and nature walks alike. They even boast a hidden pocket that’s the perfect place to store my phone during a lengthy flight. One shopper shared that they wore them during a recent 12-hour flight and noted that they were “extremely comfortable,” leading them to order “more pairs to have color options.”

Anrabess Long-sleeve Shirt

Solid-colored basics are the cornerstone of my fall wardrobe, so I can’t resist trading in my summer tanks for this boat-neck, long-sleeve from Anrabess—and at just $12, I’ll surely be stocking up on a variety of colors. The wider neckline is a fun twist on a crewneck that’ll add some variety to my wardrobe, plus since the top itself is so basic, it can be worn with practically any bottoms and styled numerous ways with simple accessory swaps. I can see myself wearing it during my next flight with a pair of leggings and sneakers, but it’ll look just as cool when worn with a breezy maxi skirt, as well. 

Project Cloud Lace-up Sneakers

Colorful sneakers can easily amp up an otherwise plain travel outfit, so I’m ready to trade in my favorite summer sandals for these Project Cloud sneakers to usher in the new season. Cushy memory foam insoles are the highlight of these shoes, practically ensuring they’ll keep me comfy during long walking days, but their non-slip outsoles are also key for staying safe when I’m running through the airport to make my next flight. Other shoppers have already awarded them their stamp of approval, with one customer revealing that they “can walk all day without the slightest pain,” raving that they “passed the travel test.”

Automet Half-zip Sweatshirt

Similar in appearance to another traveler-loved pullover, this half-zip sweatshirt will be one of the first things I add to my suitcase this fall—and it’s unsurprisingly a best-seller at Amazon. The front has one large kangaroo pocket that’ll keep my hands warm during chilly flights and hold my phone while I’m running errands, and the subtle thumbholes may just be my favorite feature. While my sweatshirt pile is moments from tipping over, after seeing one shopper calling it the “perfect quarter zip,” I think I can make room for one more. 

Earkoha Casual High-waist Maxi Skirt

For sightseeing, running errands, and everything in between, this patchwork-printed maxi skirt is about to become the most valuable piece in my closet, especially since I can wear it throughout the end of summer and well into the fall. The stretchy elastic waistband makes it especially comfy and travel-friendly, and although it boasts a bold pattern, the monochromatic shade makes it wearable with a wide range of tops. Best of all? It has pockets.  

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