Short Pants and Socks With Boots Females
These boots were made for walking. Photo-Illustration: Courtesy of retailers
We'd be willing to bet that if there's one style of shoe you slip on from late-August through mid-April, it's a pair of ankle boots. This makes sense: Ankle boots are flattering on the leg, look as good with a dress as they do with jeans, and if you land on the right pair, are just about as comfortable as a pair of everyday walking shoes can get. But, like all wardrobe staples — whether it's a white button-down or the perfectly vintage-inspired pair of blue jeans — there's a vast sea of ankle boots to pick through before landing on the ideal pair. To get a lay of the land, we reached out to 29 cool and stylish women, from the coach of Downtown Girls Basketball League to the founder of a luxury sock company, to hear about their favorite-looking pairs. And to ensure no leather and suede soles were skipped over, we scoured our archives for recommendations from other noteworthy people, including celebrities Dove Cameron and Georgia May Jagger as well as our own editors.
To help you peruse the picks, we sorted them by budget: under-$100, under-$200, under-$300, under-$400, under-$500, and splurge-worthy ankle boots. Click through to your budget bracket, or read on for all of the 35 selections that have stood the test of, well, standing — and plenty of walking, whether through slush in the winter or on long treks in the spring.
"I personally am not afraid of wearing white, especially cream, after Labor Day," says blogger and TikToker Nana Castro, which means wearing these boots year-round. "I think cream-colored boots are superchic." Not only do these boots come in a standout color, but they also have a trendy lug sole, which is really popular this fall. The elastic gusset in black gives some contrast to the shoe, adding even more edge to the style. "I would wear these with an oversize blazer, long-sleeved bodysuit, and jeans for a casual look or an oversize blazer with a slip- or minidress," says Castro.
"I tried on a ton of ankle boots last winter, including the Rachel Comey Mars booties that I really had my heart set on, and I just didn'tloveany of them," says Strategist senior writer Karen Iorio Adelson. "Either they weren't comfortable to walk in or they just hit my ankle at a weird spot." But then, on a whim, Adelson ordered the Vionics — and they were the one. "They are great — they're supercomfortable, they look sleek, and the leather is water-resistant, so you can wear them in the rain and snow," says Adelson. "They're affordable, too."
If you want a Chelsea boot with a sleeker silhouette, Bathen co-founder Hannah Zisman loves this Cole Haan pair so much that she's bought three pairs over the past ten years. It takes a lot of use to truly wear them down, though: they're made from waterproof leather and have a sturdy stacked heel. "They're durable and comfy, yet still sleek enough to wear to the office," Zisman told us. "And so much better than a rain boot, in my opinion!"
If tying and untying boot laces seems like a pain, take note from Amanda Hill, revenue strategy and operations at Twitter, who told us about her pair with a lace-zip combo from Clarks. "I like having the look of laces with the ease of a zipper," says Hill. Beyond being easy-on-easy-off, the boots are ideal for long treks: "They have a cushioned interior, which makes them probably the most comfortable boots I own," Hill says. And while temperatures may be rising now, come next winter you'll be glad to have these on hand, according to Hill. "They have great grips for ice," she says.
If all of the black boots on this list are looking a little somber for your taste, artist Maggie Meiners says that lately she's been "obsessing" over this pair from XYD, which come in 22 different colors ranging from a vibrant lime green to a pearlescent pink. "I wear my shoes and boots hard, so it's nice to have a pair I don't have to worry about too much, since the price is relatively low," Meiners says. She also notes that they're made from synthetic materials, which could be a draw for those who want to go leather-free in their footwear. Meiners told us she has the boots in white, pink, and gold.
Stylist Christel Langué is a fan of this stretchy pair of boots from Everlane. "The Glove Boot ReKnit in 'tobacco' is so chic," she says, adding that this particular shade of chocolate brown is a recent favorite color of hers. Thanks to the lowish heel, they're good for a "pain-free" day of walking, according to Langué. We can imagine wearing these with a chocolate-brown pair of Rio's favorite Wrangler men's dress jeans. The tobacco shade has since sold out, but Castro is a fan of this season's "toffee." In addition to the color, she appreciates Everlane's sustainability efforts. "These are made from renewable plastic bottles; you'd never know from the knit look," she adds.
"The best ankle boots are a sleek pair in darker tones, like chocolate brown and black, and are either square toe or pointed toe," says Bee Stuart, personal stylist and founder of Queer Yorker. These Mango boots hit all her marks. They come in a rich chocolate-brown leather and have a square toe, which she says makes them a "more modern version of the classic ankle boot and are a great way to add dimension into your boot collection." They also meet her comfort requirements. "What I've found is that they need to be one to three inches high for maximum comfort and walkability, and I recommend going up a size if you enjoy wearing thicker socks during the colder seasons," Stuart says. This heel is just over two inches, making it a walkable heel height.
Another cream-colored boot Castro won't mind wearing after Labor Day. Compared to the Open Edit pair, this is more of a combat boot than a Chelsea boot, with a lace-up design that almost makes them look like fancy Timberland boots. They are definitely a more casual option, which Castro plans to lean into when styling them. "For the Zara boots specifically, I would do the oversize blazer with biker shorts and a plain tee with gold jewelry," she says. "What I love about these boots is how anyone at any age could wear these and feel confident and stylish."
Xochil Herrera Scheer, a Chicago-based patternmaker, has been wearing these boots for the past few years "and fell in love with the unique heel style." The tapered heel gives them a Western look, as does the distressed leather finish. The heel is only two inches tall, and it's chunky, making it even more comfortable.
"I've got a passion for shiny black shoes, and these patent leather Docs go perfectly with what I wear most," says Catbird creative director Leigh Plessner, who ticks off nightgowns, long coats, full sweatsuits, and piles of jewelry as just a few of the many items that she pairs with her beloved Docs. For Plessner, the boots have a bit of appealing nostalgia to them, as well: "I sold my teenage collection of Dr. Martens on eBay, which pains me," she says. "Wish I still had them."
Photo: retailer
Strategist writer Liza Corsillo owns this pair of zip-up ankle boots (full disclosure: They were a gift) and says she "wears them all the time." She discovered them when she was writing about cowboy boots, and though this pair are technically paddock boots, they work well for city life. "They're waterproof, so good in the rain," says Corsillo. "Plus they're very, very cute with cropped denim, and they cover that weird ankle gap that always gets cold in the winter." The zipper on the front makes them easy to get on and off, too.
Jenni Lee, founder of luxury sock brand Comme Si, is also a Docs fan, though her preferred style slips on. "I love Doc Martens Chelsea Boots," she says. "They have the classic refined silhouette of a Chelsea boot, with the construction of a substantial functional boot, making them really easy to wear." Lee owns the boots in patent black, oxblood, and white leather (which she says has unfortunately been discontinued) and wears them straight through the fall into spring, with dresses and colorful socks in warmer weather. "They even look good when you're treading through city slush," she says. "And in the spring they can double as a rain boot." New York Review Books marketing manager Abigail Dunn names the Doc Martens 2976 as her go-to ankle boots, as well. "For the last two years, I've owned and heavily abused a pair without the signature yellow stitching — meaning they are a little subtler in a sea of Docs — and they go with almost anything, from 501s to flirty dresses," she says. The boots might feel a bit stiff when you first buy them, and if you want to speed up the break-in period, Dunn has a tip: "If you slather them in the Dr. Martens Wonder Balsam they break in beautifully and are pretty much indestructible, no matter the weather."
Aria McManus, captain and coach of Downtown Girls Basketball and founder of Towelkini, told us about this sleek pair of boots from Camper, which are made of waterproof Gore-Tex and have a cushioned footpad and grippy rubber soles. "They feel very futuristic, but can go with anything," she says. "Plus, it's to not have to worry about wearing them in the rain." Importantly, they're easy to wear all day long, according to McManus. "The heel height feels very comfortable," she says. "Not too low or high." She does note that the stretchy Gore-Tex material makes the shoes a little hard to get on, but "once they are on they fit like a glove," McManus says. "They feel like an extension of your feet."
"I wear white boots all fall and winter almost exclusively," says designer Tyler McGillivary. She particularly likes the patent leather of this pair because "it adds texture to any outfit," and notes that the square-shaped heel makes them "incredibly easy to walk in." The two-inch solid wood heel "gives you a lift, but doesn't feel too impractical or too fancy," she says. And the leather is high quality and wears well with time, making them an investment worth considering: "I love how flexible the leather is and how it wears into the shape of your foot," McGillivary says.
If you're a frequent Strategist reader, you might have gotten the message that our staff loves Blundstones. No less than four staffers own two pairs. Of course, we're not alone in our Blundstone fandom — the shoes are something of a cult item. Writer and senior podcast producer at the Boston Globe Amy Pedulla names them as one of her go-to ankle boots, saying, "I'm actually so surprised this company has not sponsored a podcast because nearly everyone I know working in audio wears them." Pedulla has worn Blundstone for "years and years," and is only on her second pair, thanks to the boots' durability. "They start out looking solid and matte and pulled together and then overtime blend into a smudgy comfy glove on your feet," she says. Pedulla notes that she never falls when she wears them — "I cannot say the same about clogs" — and that they work in all kinds of everyday scenarios, whether it's schlepping audio equipment, running back and forth between studios, or going for drinks with co-workers. Dancer and consultant Eva Alt agrees, saying that they're ideal "for hikes, slippery walks in the city — and they last forever." Jo Zasloff, a midwife and co-founder of nontoxic skin-care line Sisters sums it up: "Perfect everyday boot," she says.
If you like your boots with a bit of height, these just-above-the-ankle platform Docs made it on two celebrities' lists of things they can't live without: YouTuber Emma Chamberlain and actress-singer Dove Cameron. Chamberlain loves them for their height and versatility: "My first pair [of Docs] was shorter; I don't know what I was thinking because these platform ones are life-changing. They give me a rock-star feeling, like I could stomp on a drum set with my boots if I wanted to." Cameron also loves these Docs for their "badass" vibes. "When I did Marvel'sAgents of S.H.I.E.L.D., they dressed me in all these kinds of combat-esque clothes because I was a villain. They got me these massive Doc Martens because they looked really industrial. I fell in love with them. When I was done filming, I wanted to order all the stuff I wore for one outfit I was in for a lot of the time. The character was just so sexy and badass, and I felt amazing."
For even more height, try model Georgia May Jagger's favorite Docs, which are the same model as the pair above but have an even taller heel — about 2.75 inches compared to 1.75. The thick sole "makes me feel taller and also like I mean business," Jagger says.
"You can't go wrong with a black boot — never ever," says Taylor Tomasi Hill, creative and fashion director of The Yes. But this isn't just any black boot. "This sculptural pair has an updated block heel and square toe that feel both fresh and classic," Hill says. There is also a nice contrast between the leather upper and the wooden heel. These boots come from the sustainable brand Alohas. Hill says she "can get behind" its on-demand model, which means most of its shoes are available for preorder (at a discount) so that the company knows exactly how many to make and can reduce waste.
"There's a reason why there are so many iterations of the ankle boot — because it just works," says Stuart. This version combines two styles that are popular in their own right: a leather boot and a sock boot. Thankfully, these have a Balenciaga cool factor at a more affordable cost. "Leather-sock ankle boots are my absolute favorite because they have this designer element to them without the hefty designer price tag," Stuart says. "They are a modern version of the traditional sock boot, and the leather makes them super-sleek and sexy." The one concession with this shoe is the skinny heel, which Stuart notes can be uncomfortable, but because the heel height is so low (just another two and a half inches here), it makes it okay for her.
Photo: retailer
For the past four years, I've been an & Other Stories boots devotee. I've bought its heeled ankle boots, suede kitten-heel boots, lug-sole patent boots, and a pair of Chelsea boots very similar to these (mine are currently sold out). The shoes look much more expensive than they are, and I've found them to be some of the best quality leather for the price point out there. I bought my pair of Chelsea boots at its London store three years ago and have worn them in the rain and snow with almost no damage to the leather — and their chunky treaded sole is fantastic for traction on wet leaves or icy sidewalks.
If you want to introduce some texture to an outfit without getting a pair of full-on crocodile boots, an embossed pair is a nice option. This pair comes recommended by Jess Hannah Révész, founder of J. Hannah jewelry, who says the embossed and glossy leather "gives a modern femme vibe" to the slightly Western shape of the boots. Révész also points to the "slightly organic shape to the heel" as one of the design details that makes the Mateas stand out in a sea of ankle boots. Editor and writer Molly Elizalde is a fan of LoQ boots, too, and says that the heel height is "not so tall that it kills your feet to walk around in them all day," noting that she still gets plenty of compliments on the shoes "even though they're pretty worn."
Photo: retailer
Strategist writer Lauren Ro is also a fan of LoQ's boots and has its chunky heeled Lazaro boot in black patent leather. Though Ro's patent pair is no longer available on LoQ's site (it can be found in a few sizes on Poshmark), much of what she loves about her patent pair applies to the version available in soft black leather: "The heel is a great height that can look either more dressed up or casual, depending on the outfit," she says. And while Ro notes that "the ankle opening is quite tight and restrictive at first," she says that it quickly becomes comfortable: "After a few wears, it stretched out, and now I'm able to wear them without any issues." Zisman has the LoQ Lazaro boots too and says the "coveted square toe" pairs particularly well with cropped pants and jeans. Bryn Taylor, personal stylist and founder of Ouisa, likes pairing these with skirts, dresses, and leggings because of the higher shaft design. "A photographer friend of mine introduced me to LoQ a few years ago, and it has been a go-to shoe brand ever since," she says. "They use subtle details to make their shoes special without trying too hard." Taylor also co-signs Ro's claim of the boot being comfortable. She even says they "feel like slippers."
Photo: 19-08-08 julianeves PM1 B1 robst
If you're looking for a little more height, this block-heel bootie is slightly taller, giving you a three-inch lift. "Block heels are super-sexy and stylish and a great heel for evenings, and the formfitting style of this boot makes them super sexy," says Stuart. The stretch leather gives it a sleeker, almost sock-boot look without it being too tight. "This is my ideal date-night shoe for the city," she adds.
"AS98 boots are kind of like a more hip-looking Doc Martens," says environmental activist Erin Brockovich, who included these boots on her list of things she can't live without. "Some are a little more streamlined, but there are also pairs with buckles and zippers. The ones I tend to wear the most have a washed-out vintage navy look with a side zipper and buckle. I can pair them with anything. I'll even wear them when it's 90 degrees."
"When wearing jeans and trousers, I prefer the top of the boot to end closer to the ankle bone so you get a little skin showing between the edge of your pants and the boot," says Taylor. "It lets the outfit breathe a bit." If you're into that look too, she recommends Aeyde's Bea boot. "I stumbled upon the brand while mindlessly scrolling through Instagram instead of paying attention to my wife — for once, it paid off," she says. Taylor likes the subtle Western vibe they have thanks to the almost pointed toe and stacked heel. You can't go wrong with the black leather, but she also likes the "toscano suede" pictured above. If that's a little light for you and you think you might have trouble keeping them clean while walking city streets, they come in two darker shades of brown.
If the sleek style isn't quite your thing, these Ganni boots have a more tactical look to them. "There's rarely a Ganni boot I don't like, but the top industrial zipper won these an instant spot on my YES list," says Hill. They also feature a lug sole, which Hill says is both timeless and trendy. And while a trend isn't exactly what you might want to spend nearly $500 on, Hill says you'll definitely get your money's worth: "Classics like Ganni look fresh but won't feel dated in seasons to come." You might be even more tempted to keep wearing them in one of the more unique colorways, like patent burgundy and black and oyster gray.
Castro is known for finding more affordable options of the latest style, like the Zara and Open Edit boots she recommended above, but she couldn't help but add this Chloé pair to her list. "It's a very trendy boot right now," she says. They're part ankle boot but also part rain boot thanks to the all-rubber construction, which helps justify the price a little bit. It's rare you get an all-weather designer shoe that can really be worn with everything on any day. The block heel helps dress them up a bit, and they come in four different colors, so pick what goes best with your wardrobe and get the most bang for your buck.
Duck boot, but make it designer. "In every era, I've loved a duck boot: classic, heeled, over-the-knee … You name it, I've worn it," says Hill. "You can go with a classic Sperry and call it a day, but that's tough when you have beauties like Thom Browne calling your name." Sperry's are about $100, so let's break down what you're getting here for almost 12 times the price. They both have a leather upper and a rubber sole, but the real difference is in the details. The Thom Browne boots have a ridged waterproof longwing detailing on the top in black that adds a color-blocking effect next to the tan embossed rubber sole. There is also brogue detailing on the leather part of the boot and the signature striped grosgrain-loop tab at the ankle. These slight differences give the boot a more luxury look to go with the luxury price tag. And as Hill says, "The investment makes sense when you wear them year after year."
Ankle boots don't have to be practical. If you're looking for a real heeled option, fashion designer Elle B. Mambetov of Elle B. Zhou likes these four-inch stiletto sky-high boots from Christian Louboutin. "I'm one of those people that, like, I don't mind being uncomfortable if I like the outfit," she says, but she also claims that "Christain Louboutin is as comfortable as you can get if it's gonna be, like, a heel." She's a fan of the studded trim around the ankle because she likes when a boot "becomes the statement piece of the whole outfit."
Maison Margiela is another brand Mambetov likes for boot shopping. "I'm from Texas, and everyone there has a pair of cowboy boots, but I actually have a pair of Maison Margiela cowboy ankle boots that are really cool and have an open back, which is really interesting," she says. That was a few seasons ago, so there aren't many of those left, but this year she's eyeing these split-toe boots. They've got a more reasonable three-inch block heel, and you'd have to get up close to see these more understated details.
Zasloff calls this A.P.C. pair her "all-time favorite ankle boot" and says that she has two pairs that she bought years ago and still wears with everything from jeans to dresses. "I bought my first pair ten years ago in a light tan, and, at the time, they were the most expensive item I had ever bought for myself," Zasloff tells us. "But they were the best purchase, and I've bought a second pair since." The suede, she says, wears in well, and they have just the right heel height. "They are great for the person who doesn't like wearing heels," she says. "They give you a little height, but you don't feel like you are walking on stilts."
Photographer Ysa Pérez loves her A.P.C. boots too and prefers a slightly sleeker style from the brand. "I just appreciate the simplicity of what they have to offer — not too much pizzazz or options, just some great solid choices I can invest in," she says. "As a photographer, being on my feet all day is tough, and I can't just be running around in stilettos, so a nice ankle boot like this is perfect." The black "goes with everything — and especially the NYC photographer standard outfit," says Pérez, adding that the shoes are an "excellent city boot to run around in while looking fly." And, importantly, they're worth the higher price — Pérez told us the boots have lasted for years.
Photo: 18-12-11 Accessories PM1 B1 toddmaughan W
Langué also told us that you really can't go wrong with a pair of Alexander Wang ankle boots, which she says she owns in a few different styles. "No matter which ones you get, the signature cutout heel is a cool way to separate them from what everyone else is wearing," she says. And if the price tag is a bit higher than you'd usually shell out for a pair of shoes, Langué stresses the versatility of the ankle boots: "They're comfortable and easy to wear at all times of day or night" — so consider these your going to work and going out boots both.
Photo: retailer
These boots are "quite expensive," musician Alison Mosshart told us when we asked her about the things she can't live without, but "they will last your whole life" and "get better looking with time." She says she rarely takes them off. "They look kind of like Dr. Martens, but the zipper is on the back, which looks really jamming. They're the best boots, hands down. There's hardly any break-in time — I'd say just one wear. That's it. And they're so comfortable. My girlfriends and Jamie, my bandmate, all have them."
Photo: retailer
Another pair that breaks in quickly: these leather boots from Arche that actress Isabella Rossellini told us she's been wearing for 15 years. "Once I like something, I buy it year after year," she says. "And I love shoes from Arche." These boots, she says, "go with everything, and they're soft and comfortable from the first wear."
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Short Pants and Socks With Boots Females
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