Levi’s Men’s Sherpa Trucker Jacket

Trucker jackets: They’re iconic, they’re badass, and they’re the perfect layer for transitional weather that will add instant edge to any man’s style. For 40 percent off, this particular Levi’s hit (with close to 2,000 five-star reviews) is even more of a steal. Get it or regret it.

Price upon publish date of this article: $53.69

Steve Madden Women’s Dodge Sneaker

Color-happy sneakers are one of the fashion set’s favorite ways to add personality to their ‘fits this season, and the pictured Steven Madden shoe is nothing if not vivid. Savor its bright-pink beauty (with touches of black plus green in there), chunky midsole, and under-$50 price.

Price upon publish date of this article: $48.30

Lacoste Women’s Sport Ultra Dry Tennis Heritage Dress

This tenniscore-coded dress is full price on Lacoste’s site, so consider yourself lucky that Amazon now has it for 24 percent off. Though this price reduction isn’t massive, Lacoste bestsellers rarely ever go on sale (especially when they’re as in-season and trend-aware as this pick, which not only looks preppy as can be but also features moisture-wicking technology for your all-day comfort).

Price upon publish date of this article: $129.19

Tommy Hilfiger Men’s Lightweight Water Resistant Varsity Bomber Jacket

Looking to level up the way you dress this month? The Tommy Hilfiger jacket on sale for Amazon’s October Prime Day couldn’t be a better choice, as every last one of its details — from that laydown collar to the rib knit cuffs — feels elevated, without the accompanying hefty price tag. You’ll also be grateful for the bomber jacket’s water-resistant and breathable fabric, interior pocket for extra storage, and inherently modern yet timeless appearance.

Price upon publish date of this article: $60.92

Franco Sarto Womens Carolynn Lug Sole Loafer

A popular, top-rated loafer for 60 percent off? No, you’re not dreaming, though an over-$50 price reduction is, indeed, the stuff of dreams. There’s a reason the shoe style is appearing on the feet of every influencer on your FYP and the runways both — it’s able to infuse even the most casual of outfits with valuable classiness. This Franco Sarto selection has an ergonomic insole, stylish tassel detail, and 1.5-inch platform. What’s not to love?

Price upon publish date of this article: $43.89

Swarovski Stilla Attract Trilogy Drop Pierced Earrings

These feminine and radiant Swarovski earrings look like the epitome of luxury — at only $60, no less. Made with pavé white crystals in a rhodium-plated setting, the piece’s drop silhouette and stacked gems that gradually increase in size add visual interest to the mix while keeping sophistication the name of the game. “I don’t think anyone makes a finer crystal, and the process used to create these [earrings] results in a stunning stone that glimmers with extraordinary fire,” offers one passionate reviewer on the product’s landing page. We couldn’t have said it better ourselves.

Price upon publish date of this article: $66

Crocs Unisex Adult Classic Clog

Our two cents? Everyone needs a pair of Crocs clogs in their life, and you can’t get more quintessential than this particular one. Lightweight, durable, and flaunting a slip-on-and-forget design, it’ll become your trusty friend in any season — no matter if you choose to “rock the Croc” in “sports mode” (flipping the heel strap to the back) or “chill mode” (keeping things loose).

Price upon publish date of this article: $34.89

Shaperx Women’s Shapewear Bodysuit

Want to enjoy all the benefits of Skims‘ bodysuits without draining your savings account? Here’s an alternative from Shaperx, made even more affordable this Prime Day. The #1 pick in Amazon’s “Women’s Shapewear Bodysuits” category, it’s lauded for how snugly yet comfortably it sits on the body, how easy it is to repurpose the bodysuit across various genres of outfits, and how well it enhances your natural curves. Fitting all bra sizes and coming with adjustable straps, the piece will be just the thing for wearing with light-wash denim, cargo pants, and other fall fashions already in your closet.

Price upon publish date of this article: $29.63

Michael Kors Voyager Medium Tote

It’s rare to see a designer purse on sale for over half off on Amazon, even during its Prime Big Deal Days event, so this deal is truly one of those you need to snatch as soon as you see it. The Voyager Tote from Michael Kors is chic as can be (what with that logo-print canvas and gold-tone hardware); roomy enough to house your umbrella, laptop, Kindle, and more; as well as something that can totally be taken from the office to the weekend getaway with ease. We’ll only say this once: A markdown this good won’t last long, so get to shopping, stat.

Price upon publish date of this article: $119.99

Levi’s Men’s 505 Regular Fit Jeans

A good pair of jeans is nonnegotiable for autumn, and Levi’s is about as good as you can get in terms of top-quality materials, comfort, and a universally flattering fit. The beloved 505 silhouette has over 10,000 five-star reviews to its name at Amazon, with customers all over the world singing its praises. You’ll be getting a medium stonewash hue here, along with classic, straight-leg styling, a zip versus button fly, and a 100-percent, made-in-the-U.S. cotton makeup. Our favorite part? The fact that the jeans are now less than $40!

Price upon publish date of this article: $37.98

Calvin Klein Reyna Novelty Triple Compartment Shoulder Bag

Brown-colored carryalls: They’re considered hot commodities right now amongst celebs and fashion insiders alike. Join the party by snagging this 49-percent-off deal on Calvin Klein’s Reyna — a vegan leather tote in the trending-right-now caramel shade, with three internal compartments and a “perfect size,” according to multiple reviewers.

Price upon publish date of this article: $85.93

Paige Women’s Gladiolus Cashmere Sweater

Paige is most known for its premium denim selections, but this sweater makes it clear that the brand has other strong suits, too. Lightweight, made out of 100-percent cashmere, and featuring ultra-attractive puff sleeves, the sweater brings out the best in both materials and silhouette — ready to layer with everything from your maxi skirt to the barn jacket you can’t spend fall without, adding a touch of effortless femininity (courtesy of that striking Cherries Jubilee colorway) in any context.

Price upon publish date of this article: $230.30

Bagsmart Tote Bag

Puffy bags are your favorite influencer’s favorite carryall style, so you really can’t overlook this #1 bestseller in Amazon’s “Women’s Tote Handbags” category, boasting over 1,100 five-star reviews. I, dear reader, am the proud owner of one and can say with full confidence that it’s the best thing since sliced bread: able to easily house my laptop, lunchbox, makeup bag, notebook, change of clothes for the gym, and other daily must-haves without looking bulky or coming apart at the seams. Other things I love? It weighs less than a pound on its own; has comfortable shoulder straps that don’t slide off or dig into skin; comes with more pockets than you’ll know what to do with; and even has a special padded laptop sleeve for making sure your tech stays protected and scratch-free.

My two cents? Getting the Bagsmart Tote Bag — at 24 percent off — is a no-brainer.

Price upon publish date of this article: $26.59

Kate Spade New York AirPods Pro Protective Case

If you’re already the lucky owner of one (or four) of Kate Spade New York’s era-defining handbags, now’s the time to extend the collection to an AirPods case — so as to look coordinated as can be whenever you’re stepping out on the street with all your tchotchkes in tow. Compatible with 1st- or 2nd-Gen AirPods Pro, the case is drop- and scratch-proof while bestowing upon your sleek, all-white tech accessory some much-needed flair. The gleaming keychain is a looker, not to mention the piece’s tortoiseshell finish, which has a moment every fall: appearing on sunglasses, nail designs, and jewelry. Get with the trends and save big $$$ while you’re at it.

Price upon publish date of this article: $27.99

Swarovski Millenia Earrings

Octagon-cut, embedded in a setting with a rose-gold finish, and featuring sparkling-pink crystals, these earrings will make sure you’re dressed to the nines for an upcoming dinner date, gala, concert, and beyond. At a width of 0.32 inches, they’re big enough to turn heads but lightweight enough not to make your earlobes sag — an ideal balance. Swarovski guarantees that those prominent crystals will reflect the light any chance they get, becoming even more dazzling as you wear them out with cocktail dresses or even everyday outfit equations like corp-core cardigans and jeans. To ensure the heirloom-quality gems truly last a lifetime, care for them properly by “removing before contact with water, lotions, or perfumes and polishing with a lint-free cloth,” per Swarovski.

Price upon publish date of this article: $97.73

Calvin Klein Men’s Cotton Classics 3-Pack Boxer Brief

Every man needs a trusty set of boxer briefs that gets top marks in breathability, moisture-wicking capabilities, softness, and shape retention. This set is all this and more — at a whopping 41 percent off for October’s Prime Day bash at Amazon. You’ll be getting the perks of Calvin Klein’s instantly recognizable logo waistband here, as well as a longer leg line for more thigh coverage, a 100-percent cotton composition, and a contoured pouch for added support. Not a fan of heather gray? The cult-favorite brand has many more colorway options on sale where that came from.

Price upon publish date of this article: $27.21

Adidas Women’s Grand Court 2.0 Tennis Shoe

As the #1 bestseller in Amazon’s “Women’s Tennis & Racquet Sport Shoes” category, this sneaker knows what it’s talking about when it comes to the kind of lightweight comfort, durability, cushioning (thanks, Cloudfoam Comfort sockliner!), and traction that will make you win every last match without sacrificing an ounce of style in the process. To have a top-selling Adidas shoe be under $40 is pretty unprecedented, so we highly urge you to shop this half-off deal fast while your size is still in stock. Then, proceed to relish in the kick’s sleek, streamlined profile that will level up your on-court and off-court getups in equal measure. Will this become one of the best women’s white sneakers after Prime Day? Only time will tell.

Price upon publish date of this article: $35

Levi’s Women’s 94 Baggy Jeans

Levi’s is the ultimate name is denim, so imagine our surprise at the fact that one of its top baggy jean styles for women is over half off in honor of this year’s Prime Big Deal Days. “Baggy jeans are versatile, comfortable, and a staple in any wardrobe,” Joyce Lee, creative director at the luxury apparel and accessories brand Parker Thatch, told WWD for a previous story. “They can be dressed up or down depending on how you style [them].” Appearing as part of high-end labels’ collections on fall 2025 runways, the silhouette has very recently proved its alluring versatility. This particular 90s-inspired, mid-rise pick — which Levi’s calls its “softest ever,” able to “champion your curves” by creating a kind of slimming effect on the figure — will complete your fall capsule wardrobe with ease. (You’ll soon wear it on multiple days of the week, racking up compliments at every turn — mark our words.)

Price upon publish date of this article: $33.62

Sherlove Gold-Plated Knot Earrings

Already a bargain as is, these knot earrings from Sherlove have officially reached under-$10 levels, and what other excuse do you need for treating your jewelry box to something special? Hailey Bieber can’t stop wearing an almost-identical style from the brand Heaven Mayhem, but it’s safe to say this jewelry pick is far from a dupe. The drop studs are chunky, 18-karat gold-plated, fade-proof, sculptural, and on-trend as can be. They’ll flatter your ‘do and facial features as you wear them for your nine-to-five and five-to-nine plans, since the handmade earrings aren’t too flashy while exuding an undeniably luxe energy. “They look like a fancy and expensive brand but with the bonus of being affordable! Super versatile: not too dressy and too casual. I haven’t noticed any tarnish as of yet!” says one happy reviewer. Join the club before the savings expire.

Price upon publish date of this article: $9.49

Sojos Trendy Small Rectangle Sunglasses

Retro sunnies are all the rage no matter if it’s the peak of summer or the dead of winter, and this particular Sojos style has been bought over 1,000 times in the past month, according to Amazon (it also comes highly recommended by fashion It-girl Kate Bartlett). Slim, rectangular, and Y2K-coded to the max, the sunglasses are sure to complement any face shape while blocking out harmful UVA and UVB rays during those incredibly sunny fall days. The solid metal hardware here is bright gold and chic, but you also have a wide range of alternative styles to choose from for nailing the Jonathan Bailey–powered, “slutty little glasses” look that went viral this summer. The best part? The purchase comes with a microfiber pouch, microfiber cleaning cloth, and glasses box for your convenience. You’re welcome.

Price upon publish date of this article: $12.79

Chooka Women’s Waterproof Chelsea Bootie

Beloved celebrities, from Oprah to Gwyneth Paltrow, are embracing Chelsea boots with open arms as we speak, so you should definitely bless your shoe rack with this silhouette if you haven’t done so already. Bridging the gap between the casual and the formal, Chelsea booties grant ankle support, slip-on seamlessness, protection from less-than-ideal weather conditions, and a preppy-chic look that’s trending for fall 2025. This pair from Chooka has over 1,000 five-star reviews and a durable vulcanized construction out of waterproof rubber, plus a plush, faux-fur lining your toes will be grateful for. As for its outsole, pavement-gripping, no-slip traction is a sure thing here: allowing you to step out into the next rainstorm without thinking twice.

Price upon publish date of this article: $29.99