The final days of summer are officially upon us, and fall fashion is on the brain. When planning outfits for this in-between season, take it from Shop TODAY contributor Chassie Post: A one-and-done dress is your best friend.
We’ve been relying on breezy maxis to stay cool and comfy all summer, but with September just around the corner, dropping temperatures in the mornings and evenings present a whole new sartorial puzzle. Luckily, Post is lending us her expert eye for style and sharing the Amazon pieces she loves for this tricky time of year. Spanning trendy patterns and classic silhouettes, she vouches that these standouts will go the distance and help you transition seamlessly into fall.
Scroll on to shop Post’s favorite summer-to-fall dresses on Amazon, plus styling tips and expert-curated accessories for the upcoming season.
Best Amazon dresses, according to Chassie Post
“I love this boho dress! Besides being the most comfortable, easy silhouette ever (it feels like you’re wearing a nightgown), it’s great for all ages — I have one, as does my mom, a couple of her friends, my sister and a couple of my friends,” Post tells us.
“It comes in tons of colors and patterns — some super summery and some perfect for transitioning to fall. When it gets cold, I love the darker patterns with boots and even a faux fur vest,” Post notes.
As pictured above, Post styles this dress with the following Amazon accessories:
One of the biggest trends this summer has been stripes, and Post predicts the classic pattern will remain in vogue this fall.
“Stripes are always so crisp and clean and fresh looking, and one of my styling secret weapons,” Post shares, adding that she’s “a sucker” for chocolate brown and white stripes like these. “Add in the satin-style fabric and incredibly comfortable maxi silhouette and you’ll feel as good as you look.”
When styling the striped frock, Post says you can lean on your fall staples. “Pair with a sweater when it gets colder — we went with a chocolate brown slouchy cardigan, but you can also layer under a short or long sleeve tee or blazer,” she muses. “And don’t be afraid to mix patterns — I paired my dress with an animal print ballet flat (Cheetah, to be exact)... And you can also add tights or boots.”
As pictured above, Post styles this dress with the following Amazon accessories:
Another major trend this season that gets Post’s stamp of approval? Eyelet, which keeps things light and airy.
“When the temps are high, it doesn’t get any cooler than a white eyelet dress,” Post says. “But an eyelet dress in black has a whole new attitude... and with the right layers [it] can take you into fall stylishly! I paired mine with a cropped jacket with elbow-length sleeves. It’s the best of all worlds — you get the eyelet texture with transitional coverage.”
As pictured above, Post styles this dress with the following Amazon accessory:
“Polka dots have been trending for a few seasons now, and they’re not going anywhere... We’ve seen them on the runways for fall,” Post reports. “I love them and was so excited to find this little mock turtleneck number last November.”
“It’s as perfect for a hot summer night as it is a holiday party! Just switch out your sandals for pumps and add a little sparkly brooch (another fall trend!) and you can wear this dress all year long,” says Post. “I wore this dress last year on the show and got lots of compliments. Also, I’ve been eyeing the chocolate brown and white version, too! They come in tons of colors.”
As pictured above, Post styles this dress with the following Amazon accessories:
- Genshuo Kitten Heel Sandals, $44.99 (was $55.88)
- Kokoma Rhinestone Bow Brooch, $8.99
Post is calling it: this dress just might be “the” dress of the summer. The modern take on the classic shirt dress reimagines the silhouette with details like a flattering, nipped-in pleated waist and bodice, cropped oversized sleeve and midi skirt.
“We’ve also been seeing gingham everywhere and love that it can easily take you into fall, depending on the color,” Post shares. “We went for black and white, which you can wear now with sandals or transition into fall with ballet flats (preferably my favorite, leopard print!).”
As pictured above, Post styles this dress with the following Amazon accessories:
- Gtbinggo Strappy Metal Accent Sandals, $39.99 (was $44.99)
“This dress looks a whole lot like a high-end designer dress I know and love, but for a whole lot less,” Post hints. “Love the on-trend dark denim, longer midi length and flattering vertical seams. Plus, it’s got a great stretch and pockets, thank you very much!”
For a summer look, Post styled her denim midi dress with a colorful bamboo-handle bag, a silk scarf and chunky platform heels, but a more autumnal look is easy to achieve, too. “The sleeveless design is great for summer and easy to transition to fall with my favorite puff sleeve shirt,” adds Post. Also works with boots, sweaters, blazers — a four-season dress.”
As pictured above, Post styles this dress with the following Amazon accessories:
- Yuizko Bamboo Handle Bag, $36.99
- Tankaneo Puff Sleeve Button Down Shirt, $19.99 (was $29.99)
More Amazon accessories to transition seasons, according to Chassie Post
Post dresses up a look for fall by fastening a gold brooch on her jacket. She scoured Amazon and found this set of two, which can help you achieve a similar look.
Before summer ends, take a page out of Post’s styling playbook and give a square scarf a try. She ties a similar option around her head and pairs it with a denim midi dress.
This belt is a genius hack for versatile outfits across seasons. It’s great for travel, too, since you can get two different looks without packing more than one belt.
Post says this offers an affordable alternative to a similar option she owns from a luxury brand. It’s available in a few fun, bright colors, which Post gravitates toward for summer, as well as some deeper, more fall-appropriate neutral tones.
Don’t get me wrong, I swear by a big bag. But for those special occasions when I want to be unburdened, it’s helpful to have a petite clutch to pare down to the essentials. This is Post’s pick, as she reaches for a similar style when dressing up her eyelet midi dress.
Adding a dark leather accessory to your outfit instantly makes the look feel fit for colder weather. Post pairs a similar bag to this one with a patterned bohemian dress.
Whether you wrap it around your shoulders, tie it at the waist or wear it normally, the humble cardigan is a bonafide fashion workhorse. This option is Post’s pick for transitioning into fall, but you’ll definitely get plenty of wear out of it through the winter and spring, too.
The leopard print trend is coming for your footwear this fall. Be like Post and treat the eye-catching pattern like a neutral, pairing these flats with other patterns like gingham and stripes for an added style bonus.
Soak up the last of summer with a fun strappy sandal. These come in a few colors, but the snakeskin pattern is Post’s pick.
For special occasions this season, Post encourages you to break out your statement-making shoes. She wears a similar pair to this option she sent us with a red dress for a full-on holiday look.
The block heel on these boots makes them easy to stand and walk in all day, per Amazon reviewers. They’re available in eight neutral hues and two textures, faux leather and faux suede.
Give your outfit a boost with these fashionable open-toed heels, which Post says are very similar to a pair she owns and styles with a denim dress. The platform and chunky heel make them deceptively comfortable (without sacrificing style).
With a cozy suede texture and knee-high height, these boots practically scream fall. Pair them with a midi dress to transition your summer frocks into autumn.
Darker hues and leather textures make an appearance in many of Post’s fall outfits. She picked out this tote bag, which will come in handy for busy days when you need plenty of room to carry all of the essentials.
Meet the experts
- Chassie Post is a Shop TODAY contributor, TV host and lifestyle editor. Whether she’s talking fashion and beauty or home and entertaining, Post is known nationwide for covering the latest trends with her keen eye.
- Shop TODAY is a team of shopping editors and writers who spend hours every day finding the best new products, tried-and-true favorites and more finds available on Amazon that are worth shopping, according to our high standards.
How we chose
The Shop TODAY editors and writers search the internet to find the best products out there. We interview expert sources, comb through customer reviews and even use our own personal experiences to make shopping easier for our readers.
For this story, we asked Chassie Post to share her favorite dresses for summer and fall that are available on Amazon. Post also sent the Shop TODAY team some of her recommendations for accessorizing the dresses. Post tried and styled each dress herself and made her recommendations based on her own experience with the pieces.
