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| Best Seller  | Men's Santoni Chelsea Boots, Ankle Boots - Blue - Casual boots Chelsea' suede ankle boots with elastic side inserts, contrast lining, back logo tab and rubber sole. Colours: Blue Composition: 100% leather Dimension: UK MEN MPN: MGSI13414SMAISYWU60.... more | $696.00 $454.00 go to store |
 | Men's Ann Demeulemeester Stef Chelsea Ankle Boots - Black - Casual boots Synonymous with timeless elegance, the Chelsea boot gets a low-key update from Ann Demeulemeester. A menswear classic, they will go with a navy or grey suit, or with jeans and a... more | $796.18 $473.88 FREE shipping go to store |
| Best Seller  | Men's Tod's Chelsea Boot - Blue - Casual boots Classic Chelsea style defines this suave boot crafted in soft calfskin leather that's stamped at the side with the label's logo and set on a pebbled sole. Pull-on style with elastic gore insets Leather and... more | FREE shipping go to store |
 | Never Worn Before Everyday Ankle Boot With A Very Walkable Stacked Heel, In Soft Suede With Faux Shearling Lining. They Pair Well With Fall Florals, Straight-Leg Denim And Much More. Suede Upper. Faux Fur Lining. Synthetic Sole. Color: Melted Caramel... more | go to store |
 | Zara Limited Edition Blue And Black Leather Ankle Boots With Wedge Heel. Slight Nick In Left Boot Heel- See Pictures. Otherwise Perfect, Unworn Condition. more | go to store |
 | Free People Boots James Chelsea Ice Leather Light Blue Casual Heeled Ankle Womens Size: 41 Gorgeous Boots With A Light Blue Tone. Beautiful For Everyday Wear. Light Enough They Kind Of Look Off White So Could Be Pretty Neutral. New Without Tags, Some... more | go to store |
 | Tope Chelsea Boot - Blue - Fly London Boots Women's Fly London Tope Chelsea Boot - Blue - Ankle boots A treaded sole and block heel lift this classic Chelsea boot featuring logo detailing on the pull tab and a cushioned footbed. 3" heel; 1 1/4" platform 4 1/2" shaft Pull-on style with elastic... more | $299.00 $160.00 FREE shipping go to store |
 | ® Biltmore Chelsea Boot - Brown - Ugg Boots Men's Ugg ® Biltmore Chelsea Boot - Brown - Casual boots A casual performance style for urban environments, this versatile boot features weather-ready innovations like seam-sealed construction and a custom, hollow-core outsole with lightweight foam... more | $150.00 $105.00 go to store |
 | Double Zip Chelsea Boot - Black - Crown Vintage Boots Men's Crown Vintage Double Zip Chelsea Boot - Black - Casual boots Sleet-filled roads, icy sidewalks, brutally cold temperatures- there's a lot of reasons that winter is low on our list of favorite seasons. But one reason that makes it great? Being... more | $110.00 $80.00 FREE shipping go to store |
 | BOGS Kicker Rain Chelsea II - Mens 14 Navy Boot Medium *Ultra-soft and flexible rubber upper *100% waterproof *BOGS Max-Wick evaporates sweat to keep feet dry *DuraFresh natural bio-technology activates to fight odors *Pull-on styling with Neo-Tech gore for easy on *BLOOM eco-friendly, algae-based EVA... more | FREE shipping go to store |
 | Michael Kors Miller Chelsea Boot Brown 10 The Miller boot will add instant polish to denim and the season’s flirty dresses alike. Designed in a timeless silhouette, this stylish pair features stretch side panels and a back pull tab for ease of wear. The slight heel and all-around platform add... more | $255.00 $69.00 go to store |
 | Georgia Boot Blue Collar Romeo - Mens 10.5 Brown Boot Medium *With an emphasis on comfort and performance, the Georgia Boot® Blue Collar Chelsea Waterproof Work Pull-On Boot is ready to support you through hard work *Full-grain leather upper with elastic goring and front and back pull tabs *5" shaft height... more | FREE shipping go to store |
 | Georgia Boot Blue Collar Romeo - Mens 10 Brown Boot W *With an emphasis on comfort and performance, the Georgia Boot® Blue Collar Chelsea Waterproof Work Pull-On Boot is ready to support you through hard work *Full-grain leather upper with elastic goring and front and back pull tabs *5" shaft height... more | FREE shipping go to store |
 | Tecovas Men's The Chance Boots, Round Toe, 6" Shaft, Midnight, Bovine, 1.25" Heel, 13 D The Chance by Tecovas is a men's chelsea boot with western roots. It has traditional chelsea boot attributes, with a cowboy boot heel. Buy yours today! | Tecovas Men's The Chance, Round Toe Boots, 6" Shaft, Midnight, Bovine, 1.25'' Heel, Size 13 D more | go to store |
 | Tecovas Men's The Chance Boots, Round Toe, 6" Shaft, Midnight, Bovine, 1.25" Heel, 12 EE The Chance by Tecovas is a men's chelsea boot with western roots. It has traditional chelsea boot attributes, with a cowboy boot heel. Buy yours today! | Tecovas Men's The Chance, Round Toe Boots, 6" Shaft, Midnight, Bovine, 1.25'' Heel, Size 12 EE more | go to store |
 | Tecovas Men's The Chance Boots, Round Toe, 6" Shaft, Midnight, Bovine, 1.25" Heel, 11.5 EE The Chance by Tecovas is a men's chelsea boot with western roots. It has traditional chelsea boot attributes, with a cowboy boot heel. Buy yours today! | Tecovas Men's The Chance, Round Toe Boots, 6" Shaft, Midnight, Bovine, 1.25'' Heel, Size 11.5 EE more | go to store |
 | Base London Mens Garrison Plain Leather Chelsea Boots - Dark Blue - Blue - 9 - Upper: leather. - Lining: leather, textile. - Outsole: rubber. - Elasticated gusset, nylon pull tab. - Flat heel. - Cut: ankle high. - Design: logo, plain. - Toe style: round. - Fastening: slip-on. more | $130.99 $103.45 go to store |
 | Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Blue - 10 The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more | go to store |
 | Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Blue - 12 The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more | go to store |
 | Men's Call It Spring Ramiro Chelsea Boot - Brown - Casual boots Make your simple tee and navy jeans look elegant with the Call It Spring Ramiro Chelsea boot. Dual elastic panels let you comfortably wear the round-toe boot, featuring sustainable B.E.D... more | FREE shipping go to store |
 | Men's Blake McKay Stewart Chelsea Boot - Brown - Casual boots Style your navy tee and denim jeans with the fabulous Stewart Chelsea boot from Blake McKay. The water-resistant suede boot, designed with a lasting rubber sole, has dual elastic panels for... more | FREE shipping go to store |
 | Dr. Martens Edition Graeme Chelsea Boots Men's Nanamica Dr. Martens Edition Graeme Chelsea Boots - Black - Casual boots Ankle-high buffed leather Chelsea boots in black. Elasticized gusset at sides · Logo-woven pull-loop at collar · Navy stitching at heat-sealed Goodyear welt · Treaded Air... more | $180.00 $142.00 go to store |
 | Men's Tod's Leather Chelsea Boots - Black - Casual boots Chelsea boots are an enduring classic in any wardrobe. Tod's version is made from polished leather stamped with the brand's monogram and rubber pebble detailing on the heel. Wear them with... more | FREE shipping go to store |
 | Blue Bandana Malibu Chelsea Boots Men's Amiri Blue Bandana Malibu Chelsea Boots - Black - Casual boots Ankle-high denim Chelsea boots in blue. more | $730.00 $569.00 FREE shipping go to store |
 | Graphic Hardware Chelsea Boots Men's Toga Virilis Graphic Hardware Chelsea Boots - Black - Casual boots Buffed leather Chelsea boots in navy. more | $580.00 $389.00 FREE shipping go to store |
 | Kicker Ii Waterproof Chelsea Rain Boot Men's Bogs Kicker Ii Waterproof Chelsea Rain Boot - Blue - Casual boots A sturdy rubber upper adds adventure-ready durability to a sporty Chelsea boot featuring a low-profile silhouette and moisture-wicking tech for total comfort. more | FREE shipping go to store |
 | Men's Karl Lagerfeld Chelsea Boots - Blue - Casual boots Step up your shoe game with the Karl Lagerfeld Urano IV Chelsea Boot in black. Made from soft brushed leather, these boots feature a contrasting printed Karl logo on the external side, an... more | $340.91 $196.37 go to store |
 | Thermal Waterproof Genuine Shearling Lined Chelsea Boot Men's Blundstone Thermal Waterproof Genuine Shearling Lined Chelsea Boot - Blue - Casual boots This waterproof leather Chelsea boot stands up to heat and cold thanks in part to a Vibram sole, while XRD shock absorbers add all-day comfort. A removable... more | FREE shipping go to store |
 | Men's Camper Venga Chelsea Boots - Black - Casual boots Ankle-high denim Chelsea boots in black. more | $620.00 $391.00 FREE shipping go to store |
 | Men's Call It Spring Ramiro Chelsea Boot - Black - Casual boots Make your simple tee and navy jeans look elegant with the Call It Spring Ramiro Chelsea boot. Dual elastic panels let you comfortably wear the round-toe boot, featuring sustainable B.E.D... more | FREE shipping go to store |
 | Men's Vance Co. Thorpe Chelsea Boot - Blue - Casual boots Experience casual luxury with the Thorpe Chelsea boot from Vance Co. Boasting a pull-on silhouette, this ankle boot has vegan synthetic upper with stretch gore accents and wingtip detailing for... more | go to store |
 | Men's Crown Vintage Double Zip Chelsea Boot - Black - Casual boots Sleet-filled roads, icy sidewalks, brutally cold temperatures- there's a lot of reasons that winter is low on our list of favorite seasons. But one reason that makes it great? Being... more | $109.99 $79.98 FREE shipping go to store |
 | Men's Bogs Kicker Rain Chelsea Boot - Blue - Casual boots With your comfort and our environment in mind, the Bogs Kicker Chelsea rain boot is designed with an eco-friendly, algae-based BLOOM footbed in an effort to clean polluted water habitats. This... more | FREE shipping go to store |
 | Louis Vuitton Men’s Chelsea Boot Color-Navy Blue Suede Size 10 Lv 11 Us 100% Authentic Comes With Louis Vuitton Dust Bag. See Photos For Condition. Worn Once more | go to store |
 | Coach Shoes | Coach Bowery Chelsea Boot | Color: Blue | Size: 5 Blue, Suede, Coach Chelsea Boot, T Rex Charm, Slip On more | go to store |
 | These Spanish Made Leather Boots Are Such A Statement Item. They Have A Zipper Back Closure, Elastic Sides, And Cushion Insole. Such A Fun Blue Hue That You Don’t See Often In Boots. They Do Show Some Signs Of Wear But Not Much, Used And In Great... more | go to store |
 | New Without Box Insole Label Marked To Help Prevent Store Returns Free People // Paloma Barcelo Gaia - Morrison Chelsea Boots Womens Size Eur 38 Absolutely Amazing, Comfortable And Light Weight!! So Cool Spanish-Crafted Chelsea Boots Featured In A Soft... more | go to store |
 | Free People Shoes | Free People Navy Chelsea Boots | Color: Blue | Size: 7 Well Loved But Still Going Strong! Great For Running Around Town In Any Weather, Or Taking On The Town And Being Comfortable No Matter Where The Night Goes. more | go to store |
 | Free People Chelsea Boots Brooks Lug Soles In Suede Grey Blue In Excellent Condition Minor Scuff Marks Throughout A Super-Chunky Lug Sole Offers An Exaggerated Take On The Trending Utility Look For A Chelsea Boot Updated With An Elongated Shaft. 1 3/4"... more | go to store |
 | A Nice Soft Blue With Black Solid Buttons more | go to store |
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