Fashionable footwear that will keep your feet warm and dry into autumn.
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Autumn means different things to different people. For some, it’s the best time of year, thanks to football games, multicolored leaves, and cooler temps. Others dread it for many of the same reasons. Whether you’re mourning the loss of summer Fridays or dabbling in pumpkin spice everything, there’s something everyone can agree on: a good pair of boots makes stepping into the new season a breeze. (A cool, crisp, autumn breeze, that is.) Here, our top footwear picks this fall.
For warmer autumn days—ones in which sandals could be suitable, but you want to look like you’re dressing for the time of year—you’ll want these Bare Traps booties. With their low cut and cutouts around the ankle, they look sharp paired with some cuffed jeans or a sundress.
The yee-haw agenda is alive and well, and the proof is in these Jeffrey Campbell booties. With their pointed, metal-capped toes and chunky wooden heels, they give off just enough Wild West flair without feeling like chaps and a lasso are necessary to complete the look. (Though chaps and a lasso wouldn’t look bad with the boots.)
These booties have a classic silhouette, but the tiny studs around the sole give them an extra touch that places them just outside the ordinary. The shoes also offer an option to dabble in slightly out-there style, depending on which color you choose—snakeskin will give you an uber-mod look, while black and brown are more demure.
Chelsea boots—ankle-high, close-fitting boots with a low heel—are pretty much all I wear in the fall. They look smart with both pants and dresses, which helps me transition my wardrobe from summer to autumn—and this Marc Fisher style is likely to be my next pair. They have a chunky 1.5-inch heel, chic pointed toe, elastic around the ankle for easy on-off maneuvering, and their suede and imitation snakeskin uppers distinguish them from other boots.
Another stellar addition to a Chelsea boot oeuvre is this pair from Toms. They look more like a quintessential Chelsea boot, with their rounded toe, one-inch heel, and upper that hits right at the ankle. Reviewers say they’re comfortable, go with different outfit variations, and work well as a staple boot from autumn through winter.
Frye makes quality leather boots—I know this for certain because I’ve had a pair for nearly a decade, and they still look fantastic (in part due to a weatherproofing wax I treat them with once a year). The brand’s Veronica style is a magnificent entry into Frye’s offerings, with its low heel, slouchy mid-rise calf length, and distinctive silver buckle across the ankle. They look cool when worn with skinny jeans, leggings, tights, or anything else.
DSW shoppers are big fans of these faux leather G by Guess combat boots, which have nearly 400 reviews and an overall rating of 4.7 stars. Reviewers love that they zip up (instead of relying on tedious laces), have sturdy arch support, and look edgy but still coordinate with several different looks, from casual jeans and leggings to formal dresses.
These classic riding boots, with a low one-inch heel, buckle accent over the ankle, and raised flap over the knees, make for a great fall-through-winter boot. Reviewers say they’re ideal for walking around for long periods of time, wearing out to a bar, and even, yes, for riding horses. Reviewers say the calf is slim but but stretchy enough to fit different-sized calves.
Love the look of tall boots, but not sure you want to make that over-the-knee statement? These slouchy suede boots are for you. DSW reviewers love their versatility: With a heel height just under three inches and an upper that hits somewhere at the top of the calf (depending on your height), they look dramatic with a short skirt and tights or play more of a supporting role with jeans and sweaters. Their roomy shaft circumference makes them comfortable for people with larger calves.
Of course, if you do love over-the-knee boots, you can’t do much better than these from Unisa. They have an elastic tie on the back of the calf, meaning they can be adjusted for a range of body types, and a one-inch heel, which gives the wearer a subtle lift without making them look most at home on the dance floor at a club. Reviewers love that they’re easy to integrate into different outfits and actually stay above the knee, instead of slipping down like some others do.
This waterproof ankle bootie provides an upgrade for rainy weather footwear and a 3.5-inch height boost, with its concealed wedged heel and platformed toe. Save for the shoe’s extra-tractioned soles, they don’t look much different than a pair of wedge boots you’d buy just for fashion, not just function. They’re a lifesaver when rain is in the forecast but you don’t want to bust out the wellies.
These glossy, ankle-skimming boots are sure to help boost your mood on rainy days—and, of course, keep your feet dry. This Chelsea-style boot has a defined but not pointy toe, which gives them a distinctive, though not overwhelming, style.
It’s hard to go wrong with these classic rain boots. This Hunter pair is “packable,” meaning they’re lighter and easier to stow away than the brand’s original boots, but still keep out water and evoke a Kate-Moss-at-Glastonbury vibe. They also have a 16-inch calf circumference, so they should be suitable for most body types.
If you want a traditional pair of chukka boots—ankle-high, laced-up boots often made of suede or leather—you can’t go wrong with this pair of Rockports. They’re made of smooth leather, have a textured leather sole, and feel lightweight, despite their sturdy construction.
The textured details around the laces on this pair of convincing-looking faux leather boots make them stand out from others. Reviewers love that the boots are comfortable, attractive to wear with suits and jeans alike, and look more expensive than they really are.
These moccasin-inspired boots manage to feel like your oldest, most comfortable house shoes without looking schlubby. The shoes’ breathable leather mean they’re suitable for warm and cold days, which makes them perfect for those fall days when you aren’t quite sure what the weather has in store.
Another Clarks customer favorite is the Desert Boot, which has a slimmer sole and more tailored look than the Wallabees. Reviewers like that this pair is comfortable and hides dirt well, making them great for walking around cities, especially when traveling.
These boots have an air of 1970s glamour, but are still sleek, professional, and look seamless. Reviewers say makes them a great choice for daily or a night out dancing. They also have a nearly two-inch heel, which adds a bit of height for anyone who might want it.
Combat boots can be intimidating. But these combat-_inspired_ (that’s the keyword) boots look tough without seeming foreboding, and have a zipper on the side, which makes them easy to take on and off.
New Republic shoes are a favorite of Reviewed’s general manager, Chris Lloyd. And the brand’s sleek, mahogany-brown Chelsea boots are a great way to step into fall. Reviewers say they’re comfortable, go with everything, and look luxurious considering how affordable they are.
You might know of the Red Wing Moc Toe boot from The Walking Dead (the character Daryl wears them on the show). But the shoes have a lot of real-life fans, too, due to their soft leather upper, sturdy soles, and distinctive Americana look. Reviewers say the shoes are worth the investment—once they’re broken in, they feel comfortable, supportive, and last several years.
These Sorel boots are bestsellers on REI, thanks to their extra-tractioned soles, soft-yet-sturdy leather, waterproof uppers. Reviewers say they’re great for traveling, going to the office, and low-intensity hikes, and feel comfortable right when you take them out of the box—no breaking-in period required.
This pair of leather boots look like formal dress shoes, but with additional height around the ankle. This, plus their small denim decal, gives them a slightly more casual—though no less polished—look. Reviewers say the boots are comfortable for long periods of time and garner compliments from friends, family, and strangers alike.
You’re likely already familiar with Timberlands original boot, with its distinctive tan lace-up style. But if you’re wondering if they live up to their hype—wonder no more. Nordstrom reviewers say the boots are fully waterproof, comfortable, and last through several seasons of heavy use.
Another footwear option for rainy, dreary weather are the Rockport Storm Surges. These are waterproof but don’t look like a pair of galoshes—or even much different from any other casual boot. Because of this, they’re a nice choice to wear anywhere on a drippy day.
These waterproof clog-like boots aren’t fancy, but reviewers say they keep feet dry and warm in rain, puddles, and mud through the fall and winter. They’re slip-ons and have flexible rubber uppers, which makes them easier to walk and crouch in. The rubber soles offer considerable traction, too, whether you don them for gardening, errands, or walking the dog in the midst of a downpour.
Prices are accurate at the time this article was published, but may change over time.
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