As much as I love summer, I’m ready to swap out my shorts and skirts for some cozier pieces — specifically fall dresses. September is just around the corner, and while summer technically lingers until Sunday, September 22, we all know that the in-between stage can be tricky when it comes to picking travel outfits. Living in New York City, where the weather swings from scorching heat one day to a crisp chill the next, I’ve mastered the art of transitional dressing. Also, with my constant travels in the mix, I’m here to tell you that having a selection of versatile outfits is key.

One of the best solutions for this in-between season is a dress, and Amazon is stocked with stylish options perfect to wear now and well into fall. I’ve rounded up 12 of the best fall dresses under $50 that transition seamlessly into the cooler months. From sweater dresses that pair effortlessly with comfy boots, to midi dresses made for layering with jean jackets and turtleneck dresses that can be dressed up or down, these transitional fall dresses ensure there’s something for everyone. Even better: they’re also travel-friendly, versatile, and wrinkle-resistant.

Anrabess Women’s Oversized Sweater Dress

A sweater dress is the perfect piece to help you transition into fall. Among the many colors available, the brown hue stands out as a signature fall shade that instantly gets your suitcase ready for cooler days. Style it with a messy bun and high boots for a look that’s effortlessly chic. Did I mention that it’s currently 43 percent off? So even though it’s still August, now’s the time to get a head start on your fall wardrobe.

Exlura Women’s Ribbed Mini Sweater Dress

For a more elevated look, pair this sweater dress with a belt, tights, and over-the-knee boots for a dinner-ready outfit. Or, keep it casual by swapping in sneakers. The versatility of this dress makes it an ideal go-to as you move into fall, allowing you to stay warm while still looking stylish.

Zesica Women’s Midi Dress

For 48 percent off, the Zesica Midi Dress can make the change from summer to fall much smoother. Wear it with sandals while the weather’s still warm, then switch to a jean jacket and boots or sneakers as the chill sets in. The army green option is a standout — it’s a versatile color that looks great in every season.

Kranda Maxi Dress 

The Kranda Maxi Dress makes dressing for the changing seasons light and fun. The floral design keeps your outfit from feeling too wintery, while the longer length keeps your legs warm on cooler days. It’s versatile enough to wear with sandals, heels, boots, or sneakers, depending on your mood. With over 6,000 five-star ratings, one reviewer even noted that the dress “was so incredibly beautiful, comfortable, and wrinkle-free after being folded in a suitcase for travel.”

Dokotoo Short Skater Dress

One of the best things about fall is layering, which is necessary when up against unpredictable weather. On a day that still feels like summer, the Kranda Maxi Dress is an undeniable choice. The puff sleeves add a chic touch for a night out or a stylish day outing. The dress is light and breathable without being sheer, giving you the comfort you need while looking polished.

PrettyGarden Women’s Tie Waist Maxi Dress

With long sleeves and a flowy silhouette, the Pretty Garden Maxi Dress instantly strikes the perfect balance with its polyester fabric that’s neither too heavy nor too light. Many Amazon customers raved about how the fabric works in the summer, fall, and spring. The tie at the waist offers a flattering fit, so you’ll feel confident and comfortable no matter the occasion.

Anrabess Women’s Turtleneck Midi Dress

The Anrabess Turtleneck Midi Dress is a classic choice, offering endless styling options with the right accessories. On cooler days, layer it with a denim jacket or a faux fur coat and pair it with boots. For milder weather, keep it casual with sneakers and sunglasses. The subtle slit adds a flattering touch, making it a fun and stylish addition to your wardrobe.

Sampeel Sweater Dress

Priced at just $32, this dress is bound to be a staple in your September and October wardrobe lineup. It features a blend of cozy sweater material and a shorter length — ideal for fall. The warm brown shade is a timeless neutral, and it even has pockets. Dress it up with jewelry and heeled boots, or go for a laid-back look with flats or sneakers.

Zesica Women’s Midi Dress

Casual and versatile: two key qualities for any wardrobe staple. This Zesica dress offers endless styling possibilities: pair it with ballet flats for work, heels, or boots for dinner, or sneakers for a relaxed outing. It’s a breezy, lightweight, and quintessential pick for everyday wear, establishing it as a must-have for your fall collection.

Merokeety Striped T-shirt Dress

Stripes and fall go hand in hand, and this dress checks all the boxes for an effortless autumnal look. It’s casual yet polished, creating an instant outfit winner for a laid-back workday or brunch with friends. Layer it with a jean jacket or a blazer for added dimension, or stick to black accessories to keep a monochromatic vibe. With over 20,000 five-star ratings it’s earned high praise from shoppers. One reviewer raved, “The dress is super comfortable, doesn’t wrinkle, and even has pockets.”

Reoria Women’s Bodycon Maxi Dress

Available in 12 different shades, this dress is the ultimate travel companion, easily adapting to any setting. Pair it with boots and a jacket for fall, throw it on over a bathing suit at the beach, or dress it up with long earrings and heels for date night. The versatility is endless. One reviewer noted that the dress is “so flattering and comfortable to wear,” which makes it a reliable staple for any trip in my book.

Pretty Garden Maxi Dress 

Fall is when warm, earthy hues like burnt orange shine, and this dress embodies the charm of the season seamlessly. With over 3,000 five-star ratings on Amazon, it’s set to be a must-have this fall. As one customer shared, “This is so comfortable and flattering. I bought it for family photos and will definitely also wear it to the next wedding I have to attend. It’s flowy and looks more expensive than it is.” Whether you’re traveling or just enjoying the cooler weather, this dress is a perfect pick for the season ahead.

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