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| Best Seller  | Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more | go to store |
 | 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 |
| Best Seller  | Men's Frye Bowery Leather Chelsea Boots - Brown - Casual boots Frye "Bowery" Chelsea boots in burnished leather Stacked heel Round toe Elastic side goring Goodyear-welted for durability Rubber-injected lug soles Lining: Leather Made in Mexico Size... more | FREE shipping go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 2cm 100% Calf Leather, 100% Rubber. Made in Italy. more | $694.65 $566.83 FREE shipping go to store |
 | J. Crew Gray Leather Chelsea Ankle Boot. Made In Italy With 2 Inch Heel, Ankle Strap And Gold Hardware. 03868 Color: Gray Size: Women's 8 more | go to store |
 | WIDE FIT Darcy Chelsea Boot - black Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more | $99.99 $69.99 go to store |
 | Blair Men's Deer Stags Rockland Chelsea Boots - Black - 10 - Womens Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more | go to store |
 | Brand: Free People Style: James Chelsea Boots Heeled Ankle Booties Color: White Material: Leather With Rubber Gum Sole Size: Eu 40, Fits Like A 9 Has A Slightly Narrow Fit In My Opinion, Though I Do Better With Wider Fit Shoes Condition: New, No Box.... more | go to store |
 | Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more | go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 4cm, Height: 14cm, Sole: 2.5cm 100% Leather, 100% Rubber, 72% Polyester, 28% Elastane. Made in Italy. more | $662.59 $572.48 FREE shipping go to store |
 | Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. more | $732.05 $597.36 FREE shipping 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 |
 | Men's Tod's Chelsea Ankle Boots - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more | $587.78 $479.63 FREE shipping go to store |
 | Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. more | $694.65 $566.83 FREE shipping go to store |
 | Shield Square-toe Chelsea Ankle Boots Men's Burberry Shield Square-toe Chelsea Ankle Boots - Black - Casual boots 65% Calf Leather, 25% Polyester, 10% Rubber, Lining: 70% Calf Leather, 12% Polyester, 10% Goatskin Leather, 8% Rubber. Made in Italy. more | $1,106.62 $885.29 FREE shipping go to store |
 | Henry Country Ankle Chelsea Boot Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. more | $732.05 $597.36 FREE shipping go to store |
 | Men's Frye Hudson Suede Chelsea Boots - Natural - Casual boots Frye "Hudson" chelsea boots in premium suede leather Shockabsorbing EVA outsole for traction and stability 360degree Goodyear welt construction Boot shaft, approx. 6"H Chunky heel Round toe... more | FREE shipping go to store |
 | Men's Frye Bowery Chelsea Boot - Brown - Casual boots Dual goring insets and a rear pull-tab lend easy wear to a sophisticated Chelsea boot handcrafted in burnished leather for timeless appeal. Pull-on style with elastic gore insets Cushioned footbed... more | FREE shipping go to store |
 | Men's Frye Dylan Chelsea Boot - Brown - Casual boots Elevate your everyday staples with a streamlined Chelsea boot featuring flexible Goodyear welt construction and a slip-resistant rubber sole. Pull-on style with elastic gore insets Slip-resistant... more | FREE shipping go to store |
 | Men's Frye Tyler Chelsea Boot - Black - Casual boots Keep your look classic with a handcrafted Chelsea boot designed for a flexible fit and everyday comfort thanks to rubber insets in the leather sole. Pull-on style with elastic gore insets Leather... more | FREE shipping go to store |
 | Men's Frye Hudson Chelsea Boot - Brown - Casual boots A shock-absorbing EVA sole with grippy tread offers excellent traction in this Goodyear-welted Chelsea boot crafted of premium suede. more | FREE shipping go to store |
 | Men's Frye Tyler Leather Chelsea Boots - Brown - Casual boots Frye "Tyler" Chelsea boots in distressed leather Stacked heel Round toe Elastic side goring Lining: Leather Made in Mexico. more | FREE shipping go to store |
 | Men's Frye Dylan Chelsea Boot - Black - Casual boots Elevate your everyday staples with a streamlined Chelsea boot featuring flexible Goodyear welt construction and a slip-resistant rubber sole. Pull-on style with elastic gore insets Slip-resistant... more | FREE shipping go to store |
 | Men's Frye Tyler Chelsea Boot - Brown - Casual boots Go for a classic look with this handcrafted Chelsea boot designed for a flexible fit and everyday comfort thanks to rubber insets in the leather sole. Pull-on style with elastic gore insets... more | FREE shipping go to store |
 | Men's Frye Hudson Chelsea Boot - Brown - Casual boots A shock-absorbing EVA sole with grippy tread offers excellent traction in this Goodyear-welted Chelsea boot crafted of premium suede. more | FREE shipping go to store |
 | Men's Frye Tyler Leather Chelsea Boots - Brown - Casual boots Frye "Tyler" smooth leather Chelsea boots Stacked heel Round toe Elastic side goring Pull-tab at backstay Lining: Leather Made in Mexico. more | FREE shipping go to store |
 | Men's Frye Dylan Chelsea Boot - Brown - Casual boots Elevate your everyday staples with a streamlined Chelsea boot featuring flexible Goodyear welt construction and a slip-resistant rubber sole. Pull-on style with elastic gore insets Slip-resistant... more | FREE shipping go to store |
 | Men's Frye Hudson Suede Chelsea Boots - Brown - Casual boots Frye "Hudson" chelsea boots in premium suede leather Shockabsorbing EVA outsole for traction and stability 360degree Goodyear welt construction Boot shaft, approx. 6"H Chunky heel Round toe... more | FREE shipping go to store |
 | Men's Frye Tyler Chelsea Boot - Black - Casual boots This classic Chelsea boot is updated for a vintage look in ultrasoft leather for a glove-like feel, while a Goodyear welt adds durability. Pull-on style with elastic gore insets Cushioned footbed... more | FREE shipping go to store |
 | Men's Frye Austin Suede Ankle Boots - Brown - Casual boots Frye "Austin" western-inspired ankle boots in soft suede leather Stacked leather heel Round toe Supple leather lining Buckle closure at the ankle Side zip closure for easy on and off Debossed... more | FREE shipping go to store |
 | Men's Frye Conway Leather Chelsea Boots - Brown - Casual boots Frye "Conway" Chelsea boots made from durable leather Stacked heel Square toe Elastic side goring Goodyear welted construction Lining: Leather Made in Mexico. more | FREE shipping go to store |
 | Prison Lace-up Leather Ankle Boots Men's Frye Prison Lace-up Leather Ankle Boots - Black - Casual boots Frye "Prison" leather ankle boots from the made in USA collection Goodyear welted construction Stacked heel Round toe Lace-up vamp Leather lining Debossed logo Rubber sole Made in USA. more | FREE shipping go to store |
 | Tyler Burnished Leather Ankle Boots Men's Frye Tyler Burnished Leather Ankle Boots - Gray - Casual boots Frye "Tyler" ankle boots crafted from soft vintage leather with a burnished toe and heel Stacked heel Round toe Rawhide leather laces Precision stitching Rubber insets on leather sole... more | FREE shipping go to store |
 | Austin Jodhpur Leather Ankle Boots Men's Frye Austin Jodhpur Leather Ankle Boots - Black - Casual boots Frye "Austin Jodhpur" boots in smooth leather Stacked heel Almond toe Side zip eases dress Ankle strap Lining: Leather Made in Mexico. more | FREE shipping go to store |
 | Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more | go to store |
 | Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more | go to store |
 | Women's Bos. & Co. Five Waterproof Chelsea Boot - Black - Ankle boots A stretchy topline offer easy on and off in this glossy leather Chelsea boot grounded on a foam-cushioned footbed. Waterproof: protects against rain, puddles and slush to keep feet... more | $270.00 $143.01 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 Vance Co. Thorpe Chelsea Boot - Black - 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 Vance Co. Thorpe Chelsea Boot - Brown - 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 |
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