14 Best Amazon First Day of Fall Fashion Finds From $20

Fall has always been my favorite season for fashion. There’s nothing like when the weather dips to 65 degrees—sunny skies, a slight chill in the air, and finally an excuse to pull on a favorite sweater. As a New Yorker, I’m especially thankful when the new season rolls around, because it means I can step outside without instantly breaking into a sweat. Linen and pastels are officially getting swapped out for suede sneakers, moody maroons, and rich browns.

Since today is the very first day of fall, it feels like the perfect moment to share how I’m prepping my wardrobe for the season ahead. It’s hard not to go a little overboard with fall shopping, but I’ve rounded up 14 Amazon fashion finds that balance affordability with on-trend style—all while staying timeless enough to wear beyond one season. From wide-leg pants, maxi dresses and trench coats, these are the fall travel clothes I’m adding to my wardrobe ASAP. Plus, prices start at just $20. 

Best Overall Fall Wardrobe Finds

Zesica Striped Long-sleeve Top

The first thing I’m adding to my cart for fall is this striped rugby-style top. It’s an easy way to tap into seasonal trends without going overboard, thanks to the combination of three buzzy details: a polo collar, rugby cut, and bold stripes. Similar styles are popping up on designer runways and spotted on fashion insiders like Hailey Bieber and Rihanna, but here, it’s just $22—making it one of the smartest trend pieces to grab now.

Megfie Cargo Barn Jacket

Barn jackets are fall’s ultimate layering piece—lightweight but still structured, and endlessly versatile. This $40 cargo jacket find looks far more expensive than it is (comparable styles from Frame and Aritzia run hundreds). Throw it over a floral midi dress with tall boots, pair it with dark denim, or style it with leggings and ballet flats for an off-duty feel.  

Project Cloud Sneakers

Every fall wardrobe deserves a suede sneaker, and this pair hits the mark. The thin sole gives it a modern edge, while the soft texture can instantly elevate anything from silk skirts to oversized sweaters. Wear them with straight-leg trousers, sweater dresses, or leather pants—they strike that elusive balance between sporty and chic.

Baleaf Track Pants

Track pants are having their fashion moment, moving well beyond the gym. I swapped my usual black leggings for a pair of the Baleaf pants, and they add a polished twist to even the simplest outfits. They’re just as comfortable, but feel way more current. Style them with sneakers and a sweatshirt for a Sunday coffee run or dress them up with a knit and kitten heels for a night out. Bonus: they pack well and rewear seamlessly on trips.

Zesica Maxi Dress

A true multitasker, this drop-waist maxi dress works for everything from a fall wedding to a casual city stroll. The fitted bodice and flowing skirt create a flattering shape, while the breathable fabric and side pockets keep it comfortable. Depending on the occasion, pair it with boots, kitten heels, or even sneakers for a more laid-back travel look.

Odoly Clogs

Clogs are this season’s answer to the “throw-on-and-go” shoe, and at $27, this pair is an easy style win. They’re polished enough to replace slippers for errands but relaxed enough to wear every day. Pair them with jeans and a chunky sweater, wide-leg pants, or even a maxi dress—they truly go with anything year-round.

Kirundo Chunky Cardigan

This isn’t your average cardigan. The mock neck, wooden buttons, and extra pockets make it a standout piece that works both as a sweater when buttoned up or as a cozy layer over jeans or skirts. Available in rich autumnal shades like olive and burgundy, the Kirundo cardigan has that rustic-chic appeal that ties outfits together effortlessly.

Floerns Striped T-shirt

Red is a major color of the season, and this striped tee is an effortless way to work it into your wardrobe. It’s light enough for the warmer days we’re still having in NYC, but looks just as sharp layered under a cardigan or denim jacket. Try it with dark denim or gray wool trousers for a look that feels crisp and fall-ready.

Wenrine Sweater Dress

A ribbed knit dress is a seasonal classic, but this style’s stripe detail adds just enough edge to stand out. Wear it to work with a blazer and loafers, or dress it up with kitten heels for date night. It’s cozy without being bulky, making it a sleek option that transitions easily from day to evening.

Afeetsing Ballet Flats

This year, I’m leaning into navy as my go-to neutral—it pairs beautifully with denim, browns, and winter whites. These preppy ballet flats not only nail the look but also have nearly 2,000 five-star reviews. One traveler even called them the “best travel shoe,” noting they wore them across India for ten days without a single blister. 

Ewedoos Wide-leg Pants

Claiming the title as Amazon’s number one bestseller in women’s casual pants, these wide-leg trousers are a denim alternative you’ll want in multiple colors. Made with breathable, four-way stretch fabric, they’re equal parts polished and comfortable. Perfect for flights, office days, or weekend plans, they’re the kind of pants you can live in all year long.

Cicy Bell Trench Coat

Fall is trench season, and this one from Cicy Bell has become my favorite find. It instantly pulls together whatever’s underneath, whether you’re wearing jeans and a knit, a matching lounge set with sneakers, or a sweater dress with boots. It’s a timeless staple that I am constantly seeing on the streets of Manhattan.

Cider Sweater Vest

Instead of defaulting to neutrals, I’m adding this colorful sweater vest into my fall mix. With shades of green, yellow, and orange, it channels autumn without being too literal. Wear it layered over a crisp button-down for a preppy twist or solo with jeans for something more casual. Either way, it’s an easy mood-booster for cooler days.

Jusavie Tote Bag

A seasonal bag refresh is always in order, and this tote is roomy enough for work, errands, or weekend trips. The chocolate suede feels current and luxe, while the silhouette is clean enough to match everything from office-ready outfits to cozy weekend knits. I see bags like this all over NYC—practical, but never boring.

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