<p>Peculiar shoes are suddenly everywhere, and unconventional silhouettes are quickly becoming the new conventional.</p>

<p><span style="font-weight: 400;">Every so often, fashion becomes obsessed with an ugly shoe. From <a href="https://www.lofficielusa.com/fashion-week/balenciaga-spring-summer-2026-pierpaolo-piccioli-debut" target="_blank" rel="noopener">Balenciaga</a>&rsquo;s viral dad sneakers to <a href="https://www.lofficielusa.com/fashion/celebrities-spotted-wearing-mschf-big-red-boots-viral-shoes" target="_blank" rel="noopener">MSCHF's cartoonish rubber boots</a> and the many <a href="https://www.lofficielusa.com/fashion/crocs-swarovski-collaboration-shop" target="_blank" rel="noopener">Crocs designer collaborations</a> of the past years, there&rsquo;s something undeniably seductive about unsettling footwear. While many of these eccentric designs proved to be fleeting fads, freaky shoes are now taking a practical spin, becoming sleeker, smarter, and&mdash;surprisingly&mdash;more wearable than ever.</span></p>
<p><span style="font-weight: 400;">Whether it&rsquo;s an unexpected cutout, a sculptural heel, an exaggerated feature, or an unusual embellishment, freaky shoes come in many forms. There&rsquo;s no single element that makes a shoe truly freaky; it&rsquo;s more about experimental choices paired with a subtle sense of unease. To style into an avant-garde look or worn as the statement piece of an outfit, unconventional shoes are quickly becoming conventional&mdash;at least among the fashion-forward set.</span></p>
<p><span style="font-weight: 400;">And what better way to signal that unsettling shoes have entered must-have territory than New York&rsquo;s First Lady, <a href="https://www.lofficielusa.com/pop-culture/zohran-mamdani-wife-who-is-rama-duwaji-career-art" target="_blank" rel="noopener">Rama Duwaji</a>, stepping out in freaky boots for her husband&rsquo;s inauguration? Sparking heated debate online, Zohran Mamdani's wife&rsquo;s footwear choice confirmed what many already suspected: cool girls have a soft spot for the off-putting. Featuring an elongated pointed toe and leather lacing at the back, Miista&rsquo;s coven-like Shelley boots raised equal levels of controversy and fascination.</span></p>

<p><span style="font-weight: 400;">While stylist Allison Bornstein introduced her '<a href="https://www.lofficielusa.com/fashion/wrong-shoe-theory-tiktok-styling-trick-fashion-hack" target="_blank" rel="noopener">wrong-shoe theory</a>' back in 2023&mdash;encouraging dressers to finish a look with the most unexpected footwear&mdash;Mandy Lee (best known as @oldloserinbrooklyn) has become synonymous with unusual shoes on Instagram and TikTok. A longtime collector of freaky footwear, the style expert regularly shares her advice on incorporating unconventional designs into everyday outfits, spotlighting her favorite brands that range from Simone Rocha to Tory Burch.</span></p>
<p><span style="font-weight: 400;">So now you know: this year, a touch of quirkiness is encouraged. And to step into this freaky new era, we&rsquo;ve curated a selection of odd, wacky, and delightfully unsettling boots designed to carry you through the cold winter with statement-making ease.</span></p>

<p>The freaky boots chosen by <span style="font-weight: 400;">New York&rsquo;s new First Lady for her husband's inauguration&mdash;instantly making them viral&mdash;feature an exaggerated pointed toe visible from miles away. Crafted in <span>smooth goat leather, these head-turning shoes are finished with back lacing for a final touch of cool. Suitable for everything from the office to the club (and now, even political events), Miista's Shelley boots are the definition of practical freaky chic.&nbsp;</span></span></p>
<p><em>Miista Shelley Boots, $620, <a href="https://www.miista.com/en/product/shelley-black-back-lace-boots" target="_blank" rel="noopener">Miista</a></em></p>

Miista Freaky Boots

Miista

<p>Known for its modern spin on everlasting staples, Coperni's Bridge boot is one for the true experimental fashion girls. Available in a range of colorways and finishes&mdash;including this <span>snakeskin-embossed iteration&mdash;the cowboy-approved silhouette is elevated by a sculptural heel, resulting in an unexpected hybrid only fit for the brave. Whether you pair it with jeans, miniskirts, or evening dresses, this mid-calf boot turns every wintry step into a statement.</span></p>
<p><em>Coperni Gray Bridge Cowboy Tall Boots, $630, <a href="https://www.ssense.com/en-ar/women/product/coperni/gray-bridge-cowboy-tall-boots/18521971" target="_blank" rel="noopener">Ssense</a></em></p>

Coperni Freaky Boot

Coperni

<p>Because nothing makes a shoe truly freakier than the collision of opposing aesthetics, Jaded London fuses the sportiness of boxing sneakers with the sleek allure of a heeled boot. The result? A Gen-Z-approved standout shoe that turns heads with every step. Available in burgundy and black colorways, this lace-up design is finished with a charming <span>kitten heel, adding a touch of femininity to this sporty silhouette.</span></p>
<p><em>Jaded London Burgundy Brooke Boxing Boot, $195, <a href="https://jadedldn.com/products/brooke-boxing-boot" target="_blank" rel="noopener">Jaded London</a></em></p>
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Jaded London Freaky Boot

Jaded London

<p>Toteme proves that peculiarity can be minimalist, too. Defined by its subtly unsettling proportions, this low boot features an ultra-wide shaft, a p<span>ointed square toe, and a pinched seam at the vamp. Crafted from high-polished calfskin leather, its kitten heel makes it an ideal day-to-night staple for the practical freaks out there.</span></p>
<p><em>Toteme Black 'The Wide Shaft' Boots, $268, <a href="https://www.ssense.com/en-ar/women/product/totme/black-the-wide-shaft-boots/15777701" target="_blank" rel="noopener">Ssense</a></em></p>

Toteme Freaky Boot

Toteme

<p>Few things are more off-putting than hairy footwear&mdash;and Rick Owens knows it. A master of freaky designs, the American designer has spent seasons unsettling audiences with unexpected creations and singular accessories. His Concordian boot, set on a sculptural heel and lined with a fur-like texture, evokes a sense of unease only comparable to <span>Meret Oppenheim's controversial <em>Luncheon in Fur.</em></span></p>
<p><em>Rick Owens Concordians, $1.506, <a href="https://www.rickowens.eu/en/US/women/products/ro02e4879lhlcec-106" target="_blank" rel="noopener">Rick Owens</a></em></p>

Rick Owens Freaky Boot

Rick Owens

<p>Without a doubt, the Tabi is one of the most iconic unconventional shoes of all time. Maison Margiela's split-toe design, originally inspired by traditional <span>15th-century </span>Japanese socks, has sparked debate, contradiction, and admiration for decades. A true investment piece for any fashion lover, this signature style comes in endless silhouettes, colorways, and finishes. The <span>Bianchetto boot, in particular, is a perfect way to step into 2026's unbashed era of freak.</span></p>
<p><em>Maison Margiela Tabi Bianchetto Knee-High Boots, $2,300, <a href="https://www.maisonmargiela.com/wx/tabi-bianchetto-knee-high-boots-S34WW0057P4162H1532.html" target="_blank" rel="noopener">Maison Margiela</a></em></p>

Maison Margiela Freaky Boot

Maison Margiela

<p>Sculptural heels offer a sleek, sophisticated entry point into the freaky shoe frenzy&mdash;because yes, those two things can be true at the same time. Schutz's Siena booties, for example, strike the perfect balance between wearability and statement-making design, effortlessly adapting to a range of occasions. Featuring a <span>black leather finish and a sleek pointed toe, these architectural boots feel equal parts elegant and offbeat. Its standout heel does all the talking</span>, ensuring you step into any room with instant confidence.</p>
<p><em>Schutz Siena Leather Bootie, $258, <a href="https://schutz-shoes.com/products/siena-leather-bootie-f25-heel-height-high-s2248400070001?srsltid=AfmBOor6ltMdEYhFwm5vtIFMe3F_vvssQCFgel4RkbzMZeI3YFXgDoxt" target="_blank" rel="noopener">Schutz</a></em></p>

Schutz Freaky Boot

Schutz

<p>Featuring double lacing, metal hardware, mixed textures, and a sculptural heel, Damaya's Mercy boots are peak freak. <span>Made in Italy, the knee-high design isn't for the faint of heart. Offered in black, white, and brown colorways, this eye-catching design plays with contrast and structure, delivering a bold statement boot that turns every step into a certified head-turner.</span></p>
<p><em>Damaya Mercy Boot, $1,200, <a href="https://shopdamaya.com/products/mercy-boot?_pos=1&amp;_fid=247eb8243&amp;_ss=c" target="_blank" rel="noopener">Damaya</a></em></p>

Damaya Freaky Boot

Damaya

<p>Blending the offsetting allure of the Tabi boot with Sandy Liang's signature femininity, these freaky boots are defined by the unexpected. Crafted in vegan leather, the sock-like silhouette is punctuated by an oversized white pearl between the split toes. Finished with a tiny leather bow&mdash;&agrave; la Sandy&mdash;this surprising design is best worn without explanations.</p>
<p><em>Sandy Liang Pearl Sock Boot in Black, $995, <a href="https://www.sandyliang.info/products/pearl-sock-boot-in-black" target="_blank" rel="noopener">Sandy Liang</a></em></p>

Sandy Liang Freaky Boot

Sandy Liang

<p>Because no one does freak quite like the queen of punk, Vivienne Westwood's Bondage boots are made for striking steps. First introduced in the brand's <span>Spring/Summer 2002 collection, the bold design is defined by its animal-shaped toe, guaranteed to unsettle with every stride. Finished with oversized buckle straps, this three-tone boot is inspired by bondage and fetish wear.</span></p>
<p><em>Vivienne Westwood Bondage Boot, $894, <a href="https://www.viviennewestwood.com/women/shoes/boots/bondage-boot-red/71010061-11010-AM-RED.html" target="_blank" rel="noopener">Vivienne Westwood</a></em></p>

Vivienne Westwood Freaky Boot

Vivienne Westwood

<p>Neither ballet flats nor boots, August Barron's hybrid creation is made for bold dressers only. Anchored by an almond-toe flat and an ultra-wide calf, the silhouette is pulled together with leather lacing and silver eyelets. Crafted in glossy leather and defined by its unexpected proportions, the unsettling design is finished with a delicate bow for a final touch of deliberate oddness.</p>
<p><em>August Barron Black Flat Level Boots, $1,195, <a href="https://www.ssense.com/en-ar/women/product/all-in/black-flat-level-boots/18480591" target="_blank" rel="noopener">Ssense</a></em></p>

August Barron Freaky Boot

August Barron

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<p><span>L'OFFICIEL USA&nbsp;</span><i><span>may be compensated and/or receive an affiliate commission if products are purchased through our links. This item was gifted. Neither decide our editorial decisions.</span></i></p>
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Are Freaky Boots Fashion’s Next Wardrobe Essential?

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