10 Stylish and Comfy Fall Dresses I’m Adding to My Cart for Upcoming Trips — All Under $50 at Amazon

If you haven’t said it yourself, you’ve definitely heard someone say they need a vacation from their vacation after their trip is over. To minimize vacation exhaustion, I recommend packing clothes in a way that helps cut down on decision fatigue. The best way I’ve found to help with this is to pack as many dresses as possible. In fact, I’ve been on many trips where I’ve only packed dresses — including casual ones I’ll even wear on long international flights to India or Italy. Less time figuring out which top to pair with which travel bottoms means more time taking fun selfies while out sightseeing. 

Luckily, Amazon is a treasure trove of stylish and comfortable options that are also budget-friendly. And since I’m looking to do my own little seasonal wardrobe refresh ahead of the holidays and some fall weekend trips, I’ve narrowed my list down to 10 standouts. Shop a trendy denim dress from Levi’s, a comfy Gap midi dress, and several cozy sweater dress options, all of which are under $50. Just don’t be surprised if you find yourself wearing these travel-friendly outfits to holiday parties and well into the new year long after fall is over.

Levi’s Ellie Denim Dress

A denim dress like this option from Levi’s is always going to be stylish, but the minimalist design and cinched waist make this cute number look extra tasteful. It’s an easy go-to option that pairs with practically any occasion, including a short flight. This dress is made with 100-percent cotton so the fabric is going to be breathable and easy to wear in any climate. Plus, it’s more than 50 percent off.

Gap Splitneck Midi Dress

Packing light during the fall or winter can be difficult when you have to wear lots of layers, so versatility is important. I pack a midi dress like this one for every trip I go on, and I find it to be an even more flexible option in cold weather than in the summer. Pair it with boots and a cropped blazer for holiday parties, or a cardigan and sneakers for more casual occasions. This Gap dress is made of a stretchy fabric that’s ultra comfortable, and while it’s available in classic black, I’m eyeing the holiday-ready emerald green shade. The cinched A-line silhouette never goes out of fashion.

The Drop Shelly Deep V-neck Maxi Dress

Admittedly, I used to think maxi dresses would make me look like I was drowning in a shapeless bag, but that was before I decided to try one. Now, I have about a dozen sitting in my wardrobe and maxi dresses have become my favorite items to pack on vacation year-round. They look elegant but feel just as comfortable as my cozy nightgowns. Available in three colorways, this billowy V-neck option from The Drop has a chic and sophisticated look that can easily work as a fall wedding guest dress, thanks to the A-line silhouette and expensive-looking silky fabric. Haven’t heard of The Drop? It’s Amazon’s collection of fashion influencer-designed items, and the brand is one of my favorite hacks for shopping on a budget.

Amazon Essentials Maxi T-shirt Dress

A T-shirt dress never lets you down. It works for flights, pairs well with a denim jacket while out running errands, or can be worn to a nice dinner with some bold jewelry and ankle booties. This stretchy jersey-fabric option has a cold weather-friendly maxi length that just screams “cool girl”. My sister owns this particular one in several colors, and while you can never go wrong with black, I highly recommend the burgundy option for this time of year — though it won’t hurt much to grab a few since this is just $26 right now. It’s so comfortable, my sister wears this with a cardigan for long international flights and finds it easy to sleep in.

Anrabess Cable Knit Sweater Dress

No matter how cute an outfit looks, I know I won’t actually wear it if I don’t feel comfortable in it. That’s why I am so excited that this dress is in an Amazon truck on its way to me right now. Made with a soft, cable-knit fabric that offers a bit more warmth than a standard mini dress, I look forward to pairing this with some tights and knee-high boots for Thanksgiving. My shopping editor pro tip? Wear these fleece-lined tights in the winter time for a sexy look that doesn’t compromise on warmth and comfort.

Grace Karin Ribbed Sleeveless Turtleneck Dress

There’s something about a black turtleneck that just looks so classic and charming. (Just call me Steve Jobs.) This option, made with a cozy ribbed fabric that won’t wrinkle in your suitcase, has a stretchy and lightweight feel. The slits on each side give this dress a flirtatious vibe, and while the tie at the waist looks nice as-is, you can level up the glam quotient by using your own belt to match your shoes and purse.

Newshows Sweater Wrap Dress

The wrap dress trend isn’t going anywhere any time soon, so you can trust that you’ll be wearing this option annually for years to come. Available in 22 colors, the dress is made with a cozy sweater-like fabric, and I predict you’ll reach for it for holiday parties or dinner out at your destination. Not only will you win serious style points but you’ll be oh-so comfortable, too.

Hooever Corduroy Overall Dress

An overall-style dress, like this corduroy option from Hooever, is always going to be stylish. It layers easily on top of a fitted turtleneck or sweater, and you can even wear it on top of a button-down shirt for more dressy occasions. This is just $26 right now with the on-site coupon, which is a steal for a dress reviewers say is “really comfortable” and “great quality.” 

Merokeety Collared Maxi Sweater Dress

In my fall style rotation, button-ups, maxi dresses, and sweater dresses are a frequent occurrence, and this dress combines that holy trifecta into one charming choice. This travel-friendly dress is going to be comfy enough to wear with a cardigan and cozy boots on my short flight to visit family in Canada, and then again with a cropped black cardigan and some leather boots when I want to dress up. 

Ecupper Polo Athletic Dress

I occasionally ditch my “city girl” persona to go on a hiking trip, which is why this athletic dress is in my cart right now. At under $50, this offers great value for the quality and style, and I look forward to wearing it on a weekend trip I have planned this fall. The hidden boyshorts, secret pockets, stylish collar, and thumb holes are enough for me to know that I’ll be wearing this on repeat for years to come. 

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