The Best Fall Boots on Amazon, According to a Style Writer

This was another one of my stellar shoe purchases last year. The Naturalizer Deesha Bootie is one of the comfiest boots I own, and it’s the boot I almost always opt for when I want a shorter shaft. The height is perfect for wearing under jeans or wide-leg trousers (a combo I wear on repeat all fall). I opted for the chocolate-brown leather, which looks great with pretty much everything in my autumn wardrobe. The heel is just a hair over two inches for a little lift and has a flared base, making it insanely easy to walk in. It also has a tonal stretchy panel on one side and a hidden side zipper for easy access.

If you’re looking for an ankle bootie with a bit more heft, I’d choose the Alivia. I have two pairs of boots from Lucky Brand (that I can no longer find online—womp), and they have held up remarkably well over the past 4 years while being super comfy since day one. This ankle bootie has a much thicker and taller 3-inch heel than the Naturalizer pair. In both the brown and black colorways, the heel matches the rest of the leather exterior for a high-quality finish. Plus, the almond-shaped toe doesn’t stand out as much as a pointed or square toe, meaning it will pair well with basically any outfit.

I’ve had my eye on the ever-popular Frye Campus Boot for a while, but the nearly $500 price tag is difficult to justify. The Dream Pairs Square-Toe Riding Boot is a 10th of the price and has a similar equestrian-inspired look, including that rich banana shade (along with classic neutrals). The 1.8-inch heel is low enough that it barely reads as a heel, but still gives you a little lift, and the squared-off toe looks great with casual fits. I’d wear this boot with a mini skirt and an oversized sweater, or tuck leggings or skinny jeans into the boot with a turtleneck and a jacket.

Chelsea boots are having a moment again, and I get the appeal: They’re easy to pull on and work with just about any fall outfit. The Athlefit Slip-On Chelsea Boot is a great budget-friendly way to try the trend without spending a ton. It has stretchy side panels and a pull tab for easy on-and-off, plus a chunky sole with plenty of lugs for a little edge (and grip outdoors). The 2.3-inch heel adds some height without feeling too dressy, and you can choose between suede and faux leather depending on your style. I’d wear this boot with straight-leg jeans and a sweater for everyday, or with a skirt and tights for fall festivities at the pumpkin patch or vineyard.

Need something cozy for casual hangs or fall errands? Then I suggest this cozy ankle boot from Cushionaire. It has a similar vibe to the Ugg Classic Ultra Mini for a fraction of the cost. I snagged the Cushionaire a while back to see if I would wear it enough to justify splurging on another pair of Uggs, and I was way more impressed with the comfort and the look of it than I expected. The faux fur lining isn’t as warm or cozy as some of my other Ugg boots and slippers, but it comes pretty darn close. Plus, it’s made with genuine suede on the outside, so it definitely doesn’t come across as cheap. I love throwing this boot on with a pair of baggy jeans and a sweater for a casual-cute fall fit.

Few things signal the arrival of fall quite like a pair of suede boots—and this knee-high pair is totally giving Rory Gilmore and Stars Hollow energy. I love the chunky heel and almond toe. The 2.3-inch heel and blocky shape make it easy to walk in for hours. It comes in four autumnal shades that are all perfect for styling with sweaters, tights, mini skirts, and denim.

If your fall mood board leans more biker chick than Gilmore Girls, the Vepose Moto Boot deserves a look. It has all the details you’d look for in a moto boot, from the squared toe that curves slightly upward to the low block heel and ankle-high shaft with pull tabs. The best part is the detachable harness straps, which have metal rings for that full-on motorcycle-inspired look. But they can be removed when you want something a little less edgy. I’d wear this with straight-leg jeans and a leather jacket for a little off-duty rock star energy or let them toughen up a floaty dress.