It’s Confirmed: the Best Fall Shoe Deals Under $100 Are Hiding on Zappos

All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.

If there’s something about fall that makes you want to reinvent your style, I feel you. But if refreshing your entire wardrobe isn’t financially feasible—or you’d rather tackle it in batches—start with your shoes. After all, the right pair can make or break an outfit. And you don’t have to spend a fortune to give your rotation a seasonal refresh because Zappos has over 6,000 fall shoe deals under $100, including discounted boots, sneakers, loafers, and more from buzzy brands like Steve Madden, Naturalizer, and Vans. Here are the 12 trendiest steals we think are most worth your coin—starting at just $39.

Related Stories

These Under-$25 Secret Santa Gifts Are So Good, Your Partner Will Think You Went Over Budget

The 35 Best Survivor Gifts, According to a Superfan—Including Jeff Probst Merch

Zappos Fall Shoe Deals Under $100 at a Glance

• Best Loafer Deal: Steve Madden Langsten, $60 (originally $100)
• Best Boot Deal: Bearpaw Super Shorty, $55 (originally $80)
• Best Sneaker Deal: Gola Elan, $78 (originally $120)
• Best Flats Deal: Lucky Brand Emmie, $41 (originally $59)
• Best Heels Deal: Naturalizer Huntley, $75 (originally $110)
• Best Clog Deal: Crocs Classic Lined Clogs, $39 (originally $60)

Steve Madden Langsten

On Sale 40% off

$60 Buy Now

We’re calling it: Chocolate brown suede will be everywhere this fall, and these chunky Steve Madden loafers are proof. BTW, suede loafers in any color and from any brand for a discounted $60 is a definite steal.

Sizes: 5.5-10
Colorways: 1

Naturalizer Huntley

On Sale 35% off

$75 Buy Now

If you work in an office that enforces a more formal dress code but topple over every time you wear pumps, it’s time to grab a low, block heel like this one. Naturalizer is all about creating supportive footwear, which is why the Huntley features REZORB responsive cushioning for shock absorption and impact protection for sneaker-level comfort. These heels are so simple yet so sophisticated—and they’re somehow down to $75 (a whole $40 in savings!).

Sizes: 6-9, including half sizes
Colorways: 3

Gola Elan

On Sale 35% off

$78 Buy Now

If you’re feeling Samba fatigue, now’s your chance to branch out with Gola’s Elan sneaker, which is an impressive 35% off right now. It has the Sambas’ same low-profile silhouette but comes in fresh color combos.

Sizes: 6-10, including half sizes
Colorways: 16

Steve Madden Hunny

On Sale 18% off

$90 Buy Now

Autumn isn’t complete without a classic black pair of boots. These ones from Steve Madden are giving subtle witchy vibes and could be great for dressier occasions. And quite frankly, I’m shocked you can find a pair of heeled leather boots for under $100 at Zappos.

Sizes: 6-10, including half sizes
Colorways: 3

Eastland 1995 Edition Classic II

On Sale 20% off

$92 Buy Now

While I’m personally a loafer hater because they were part of my high school uniform, it seems like everyone around me is click-clacking in them. This year, I’m noticing flatter styles trending, rather than chunky options. Pair Eastland 1995 Edition’s Classic II loafer with ankle socks, any silhouette of jeans, and an oversized sweater for the ultimate fall ‘fit.

Sizes: 5-12, including half sizes
Widths: M, N, W
Colorways: 5

Vans FU Super Lowpro Mules

On Sale 30% off

$56 Buy Now

I immediately clicked into these Vans mules while browsing Zappos’ sale section. They look so retro and low to the ground, and this gray version would look très cute peeping out from under some baggy jeans. It’s also pretty rare to find Vans and similar popular sneaker brands selling kicks for under $60, so pass up this unique style!

Sizes: 5-11, including half sizes
Colorways: 2

Bearpaw Super Shorty

On Sale 31% off

$55 Buy Now

Can’t shell out over $100 for cozy boots? Bearpaw’s Super Shorty are down to just $55, which is significantly less than the OG UGGs.

Sizes: 5-11, no half sizes
Colorways: 4

White Mountain Bueno

On Sale 24% off

$60 Buy Now

Birkenstocks likely come to mind when you look at White Mountain’s Bueno clogs. These shoes feature a suede upper, contoured footbed, and cork midsole, but my favorite design element is the oversized buckle. Also, they cost $100 less than their iconic counterparts.

Sizes: 5-11, no half sizes
Colorways: 4

Lucky Brand Emmie

On Sale 31% off

$41 Buy Now

Tiny, simple ballet flats are trendier than ever. In fact, I think this style is getting smaller and smaller to the point where you could consider them barely-there shoes. This pair from Lucky Brand is exactly what I’m talking about, and I adore the criss-cross detailing in the back. Not to mention, they’re a whopping 31% off at Zappos.

Sizes: 5.5-11
Widths: M, W
Colorways: 1

Dr. Scholl’s Time Off

On Sale 32% off

$75 Buy Now

We name Dr. Scholl’s’ Time Off sneakers in our roundup of the best shoes for traveling Europe, but you should really consider them as an everyday, everywhere option. They contain an anatomical cushioning insole that has anti-microbial and anti-odor technology, plus the 1.5-inch platform gives you extra height.

Sizes: 6-11, including half sizes
Colorways: 7

Aerosoles Camera

On Sale 33% off

$84 Buy Now

I’m so tired of heels that make my feet feel like they’re splitting in half, so if I do need fancier shoes, I’m going straight to brands that are known for cushioned, supportive designs. Aerosoles is one of them, and the Camera Sandal proves you can look stylish while staying comfy. They have a block heel, a proprietary Diamond Flex™ outsole, a cushioned ortholite foam insole, and flexible straps. Pick up this gold colorway for fall and winter—it’s shiny yet subtle for all your holiday functions.

Sizes: 5-12, including half sizes
Colorways: 6

Crocs Classic Lined Clogs

On Sale 35% off

$39 Buy Now

You can’t celebrate cozy season without comfortable shoes like coveted Crocs. This pair is covered in a soft, fuzzy liner for extra cushion. Plus, they’re marked down by $21!

Sizes: 4-13, no half sizes
Colorways: 3

Why you should trust StyleCaster

The StyleCaster shopping team is dedicated to finding the best products, brands, services, sales, and deals across fashion, beauty, lifestyle, and entertainment. We make sure to stay on top of the latest trends, too. From knowing a brand’s offerings like the back of our hands to updating prices, hunting down discount codes and hacks, to identifying alternatives, we do a thorough job of suggesting products that deserve your attention and money. Additionally, our commerce writers and editors have previously covered a vast array of online clothing sales, so we know a thing or two about which savings events are worth checking out.

This story’s author, StyleCaster commerce editor Katie Decker-Jacoby, scours the internet for the best of the best to ensure readers walk away with items recommended by our team, industry experts, and more. She has covered an ungodly amount of clothing sales. Most recently, she’s worked on Abercrombie sales, Nordstrom’s Anniversary Sale, and Quince’s Fourth of July sale, among others. She has also been cranking out coupon pages for Quince, Abercrombie, Macy’s, Gap, and many more.