Although undoubtedly one of the most enjoyable times of year, boot season is also one of the most dangerous for our bank accounts. Right now, the new crop of styles is fresh in stores, and no matter what you’re in the market for—over-the-knee, stack-heel, Chelsea, lace-up—there are are likely several dozen pairs out there that will inspire serious need-it-now feelings.
Believe me, I know the feeling: no matter how close my apartment floors come to being overtaken by stray footwear, the urge to expand my collection tends to hit right around this time (probably not coincidentally, right at the end of Paris Fashion Week).
And if the STYLECASTER staff Slack channels—not to mention the texts from friends wondering which black booties are the best black booties because ohmigod there are so many black booties out there—are anything to go by, I’m not alone here: it’s prime shopping season, and sometimes, the sheer magnitude of options can be overwhelming.
More than sandals (which, let’s be honest, tend to get worn to the ground in a summer or two), boots can be a justified investment. But do you go the safe route and buy another classic black pair you know you’ll get a ton of use out of, or go for that of-the-moment style you can’t stop thinking about? And do you throw down a lot of cash on a designer that you know (or at least hope!) will last, or opt for the cheap-and-cheerful version from Zara et. al?
These are the questions we’re grappling with these days (you know, when we’re not thinking about the Election or the wage gap or society’s questionable treatment of Kim Kardashian)—so, to that end, I asked our editors to share their absolutely favorite picks of the season—one out of budget but oh-so-dreamy, and one affordable and more realistic. Click through the slideshow to see them all!
"I love that these are a classic Chelsea boot with a zany, off-beat twist, which I feel also describes me as a person. They speak to me on a highly spiritual level. In other words, I need them."—Christina Grasso, social media manager
Fendi Bug Leather Chelsea Boots, $1,050; at Saks Fifth Avenue
"My clothes are all black but my soul is a metallic #tumblrpink, so these would be a perfect way to enliven a monochromatic look."—Christina Grasso, social media manager
Mercury Soft-Toe Ankle Boots, $130; at Topshop
"I’m not usually one for a wooden stacked heel—nor do I own anything that isn’t black, white, or grey—but these khaki suede ankle boots caught my eye a few weeks ago and I bookmarked them as though I’d ever actually spend $1K on shoes." —Lauren Caruso, site director
Isabel Marant Garrett Suede Ankle Boots, $940; at Net-A-Porter
"These slim-ankle leather booties from—where else?—Zara have a much higher chance of ending up in my closet."—Lauren Caruso, site director
Leather High-Heel Ankle Boots, $119; at Zara
"Do I need another pair of black booties? Debatable. Do I desperately want this cool-as-hell velour Ferragamo pair? Absolutely. The carpet-y texture and '70s-style pattern are unique enough to almost justify the price tag. Almost."—Hilary George-Parkin, fashion editor
Salvatore Ferragamo Feel Plush Booties, $1,890; at Nordstrom
"I've really been feeling (faux) python lately, and the slightly longer shaft on these ankle boots feels very 2016. Plus, they're by a Canadian brand—represent!—that I've been Insta-stalking for a while now."—Hilary George-Parkin, fashion editor
Jillian Snake Boot, $142.99 (was $178); at L’Intervalle
"I recently told my colleagues that I was launching a Kickstarter for these, and I was only half-kidding. The tortoiseshell heel is perfect, and while it may sound cliché, this really is a goes-with-everything shoe. "—Leah Faye Cooper, editorial producer
Stella McCartney Tortoiseshell Block-Heel Faux-Leather Ankle Boot, $665; at Matches Fashion
"I’ve been on the hunt for an everyday bootie and this one might be it. I love that the heel is prominent but not so high that I’ll be uncomfortable walking around in them all day."—Leah Faye Cooper, editorial producer
Halogen Cori Round-Toe Bootie, $129.95; at Nordstrom
"I know: so unoriginal and not even a new obsession, but I have been lusting after these beyond-perfect over-the-knee boots for so long, they’re impossible to get out of my head. And yet, so is their steep price tag—which is why, after several seasons of from-afar admiration, I still don’t own them."—Cristina Velocci, managing editor
The Highland Boot, $798; at Stuart Weitzman
"I’m not sure I need yet another pair of black booties this fall, but I’m willing to make room in my closet for these. The brushed-gold stacked heel is a special twist on the fall staple, yet still insanely versatile and practical for everyday wear."—Cristina Velocci, managing editor
Cynthiam Booties, $129.95; at Steve Madden
"Something about these embellished Valentino boots appeals to me on such a deep level—the high-schooler in me is obsessed, but I can also see myself wearing them with black jeans and a black top all fall and into the winter. I wish."—Bibi Deitz, news editor
Valentino Butterfly-Appliqué Suede Ankle Boots, $2,145; at Matches Fashion
"Same silhouette, but vastly more affordable, these Zara babies aren’t embellished, per se, but the metallic cap toe makes them feel fresh and modern."—Bibi Deitz, news editor
High-Heel Leather Ankle Boots with Metallic Toe, $119; at Zara
"I love how versatile these are—they'd go with anything from a dress to jeans. They look comfy, too, with a chunky heel, but the cutout makes them a little edgier."—Hannah Hickok, lifestyle editor
Alexander Wang Gabi Cutout Suede Ankle Boots, $650; at Net-A-Porter
"I'm a fan of these sleek pointy-toe booties by Kendall and Kylie. The stacked heel makes them practical, but the sculpted top makes them sexier and more unique than your average ankle bootie."—Hannah Hickok, lifestyle editor
Kendall + Kylie Finley Leather Booties, $190; at Shopbop
"These 5050 boots have been on my lust list for a good five years now … and they’ll probably stay there until I win the lottery. I love the dual-leather look of the Nappa black, and I’m even more excited that these come in wide—a super, super rare feature of pretty shoes."—Chloe Metzger, beauty editor
The 5050 Boot, $650; at Stuart Weitzman
"I have a wide foot—like, think duck feet—and it’s nearly impossible to find cute boots that come in wide that don’t look like my grandmother owns them. These leather booties are durable, cute, and delicately trimmed for a little somethin’ somethin’ extra."—Chloe Metzger, beauty editor
Sudini Felicia Lace-Up Boot, $194.95; at Nordstrom