Best Seller
Tory Burch Shoes | *00342-002 New! Tory Burch Boots Miller 50 Mm Lug Sole Bootie Sierra Antik-Calf | Color: Black | Size: 8

Tory Burch Shoes | *00342-002 New! Tory Burch Boots Miller 50 Mm Lug Sole Bootie Sierra Antik-Calf | Color: Black | Size: 8

My Favorite! Most Fabulous, Chic, And Sexy! New! Tory Burch Boots Miller 50 Mm Lug Sole Bootie Sierra Antik-Calf Side-Zip Closure And Lace-Up Front Panel A Secure Fit. Classic Round Toe. Rear Pull-Tab For Easy Entry. Signature Logo Accent At The Side.... more

$385.00

go to store
Tory Burch Shoes | - ** New** Tory Burch Ruby 90 Mm Bootie- Sierra Antik In Perfect Black Siz | Color: Black | Size: 11

Tory Burch Shoes | - ** New** Tory Burch Ruby 90 Mm Bootie- Sierra Antik In Perfect Black Siz | Color: Black | Size: 11

Tory Burch Rubby 90 Mm Bootie Sierra Antik Size 11 In Perfect Black Side Zip Closure Leather New In Box And Dust Bag Included more

$297.00

go to store
Best Seller
Anthropologie Shoes | $160 Dolce Vita Buckle Brown Leather Sierra Bootie Ankle Boots [9.5] | Color: Brown/Tan | Size: Various

Anthropologie Shoes | $160 Dolce Vita Buckle Brown Leather Sierra Bootie Ankle Boots [9.5] | Color: Brown/Tan | Size: Various

A Perforated Counter Offers A Subtly Edgy Look To An Almond-Toe Bootie Shaped From Smooth, Burnished Leather And Set On A Low, Stacked Heel. A Belted Shaft And Tasseled Zipper Complete The Look With Trend-Savvy Appeal. 1 1/2" Heel Side Zip Closure.... more

$160.00

go to store
Dylan Chelsea Bootie - Black - Stuart Weitzman Boots

Dylan Chelsea Bootie - Black - Stuart Weitzman Boots

Women's Stuart Weitzman Dylan Chelsea Bootie - Black - Ankle boots The DYLAN CHELSEA BOOTIE will lend polished edge to any outfit thanks to its sleek silhouette and rugged lug sole. This ankle BOOTIE is crafted with elastic side gussets and a pull tab... more

$650.00 $209.00

FREE shipping

go to store
Western Chelsea Bootie - Brown - ANN MASHBURN Boots

Western Chelsea Bootie - Brown - ANN MASHBURN Boots

Women's ANN MASHBURN Western Chelsea Bootie - Brown - Ankle boots Stretchy paneling and easy-on pull tabs serve grab-and-go comfort in this rugged, Chelsea-inspired Western boot complete with decorative stitching. 2" heel (size 9US/39EU) 5 1/2" shaft... more

$595.00 $357.00

FREE shipping

go to store
Farlin Chelsea Bootie - Brown - Dolce Vita Boots

Farlin Chelsea Bootie - Brown - Dolce Vita Boots

Women's Dolce Vita Farlin Chelsea Bootie - Brown - Ankle boots Everyone needs a classic pair of boots that they can reach for once the weather starts to dip. The Farlin booties from Dolce Vita will become your go-to pair thanks to their quality suede... more

$70.00

go to store
Muck Boots Chore Classic Chelsea Boots - Men's Black 10 CHC-000A-BLK-100

Muck Boots Chore Classic Chelsea Boots - Men's Black 10 CHC-000A-BLK-100

Muck Boots Chore Classic Chelsea Boots - Men's Black 10 CHC-000A-BLK-100. These from Muck Boots are crafted with a 5mm neoprene bootie to keep your feet comfortable and protected. For extra-strength protection the Muck Chore Classic Chelsea features... more

$135.00

FREE shipping

go to store
Tory Burch Shoes | Chelsea 70mm Lug Bootie | Color: Black | Size: Various

Tory Burch Shoes | Chelsea 70mm Lug Bootie | Color: Black | Size: Various

New W/O Tags more

$375.00

go to store
Free People Shoes | Free People Chelsea Booties In Khaki | Color: Green | Size: 6.5

Free People Shoes | Free People Chelsea Booties In Khaki | Color: Green | Size: 6.5

Free People Chelsea Booties In Khaki. Heel 3.66 In. Super Comfortable And Easy To Clean Scuff Marks. more

$115.00

go to store
Torrid Shoes | Lug Chelsea Bootie From Torrid | Color: Brown/Tan | Size: 7.5

Torrid Shoes | Lug Chelsea Bootie From Torrid | Color: Brown/Tan | Size: 7.5

Boot Runs Big Fits Like An 8 1/2 Comfortably Product Details Fit Extra Wide Width (Ww): Our Unique Fit Gives You Extra Wide Width And Extra Room Around Your Whole Foot. Extra Cushioned Footbed. Heel Height: 2.5" Materials + Care Man-Made Materials.... more

$65.00

go to store
J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

J Crew Cognac Brown Leather Chelsea Boots With Stretch Panels For Easy Pull-On. Tag Size 8. Fits 7.5-8 In My Opinion. Style Eo824 Preowned. Shows Signs Of Wear Including Scuffs On Toes, Wear On Back Heels, Wear On Bottoms Of Soles, Creasing In Midfoot... more

$50.00

go to store
Free People Shoes | Free People Atlas Studded Chelsea Bootie Size 10 Brown Nwot | Color: Brown/Gold | Size: 10

Free People Shoes | Free People Atlas Studded Chelsea Bootie Size 10 Brown Nwot | Color: Brown/Gold | Size: 10

Bought A Year Ago From Nordstrom And Wore For Two Hours. Which Is Why I Say Nwot Because There Is No Wear, They Are As Good As New. I Couldn’t Resist Getting Them Even Tho I Needed A Half Size Bigger. Same Fashion Story, Thought I’d Make My Feet... more

$87.00

go to store
Coach Shoes | Coach Lyden Chelsea Bootie Walnut Brown Leather Size 9.5 | Color: Black/Brown | Size: 9.5

Coach Shoes | Coach Lyden Chelsea Bootie Walnut Brown Leather Size 9.5 | Color: Black/Brown | Size: 9.5

New Without Tag/Box. Very Light Creating From Being Tried On. more

$125.00

go to store
Coach Shoes | Coach Bowery Tea Rose Cutout Chelsea Bootie 9 | Color: Brown | Size: 9

Coach Shoes | Coach Bowery Tea Rose Cutout Chelsea Bootie 9 | Color: Brown | Size: 9

Coach Bowery Tea Rose Cutout Chelsea Bootie Color: Saddle Size: 9 Msrp: $395.00 Floral Cutouts Add A Fresh Twist To A Quintessential Chelsea Boot Set On A Stacked Heel. - 1 3/4" Heel - 5 1/2" Shaft - Removable Charm - Leather Upper/Leather And... more

$245.00

go to store
Free People Shoes | Free People Atlas Puffer Chelsea Black Booties E 935 | Color: Black | Size: 9

Free People Shoes | Free People Atlas Puffer Chelsea Black Booties E 935 | Color: Black | Size: 9

Preowned Shoe Shaft Style: Ankle Character: Boots Us Shoe Size: 9m Color: Black Heel Height: Flat (Under 1 In) Brand: Free People Type: Boot Department: Women Heel Style: Block Model: People Atlas Chelsea Exterior Color: Black Style: Bootie Outsole... more

$72.00

go to store
Coach Shoes | Coach Women’s Lyden Leather Chelsea Bootie- Walnut | Color: Brown | Size: 10

Coach Shoes | Coach Women’s Lyden Leather Chelsea Bootie- Walnut | Color: Brown | Size: 10

Leather Upper Man-Made Leather Lining And Footbed Rubber Outsole Pull On Shaft: 4 3/4" Height, 9 3/4" Circumference 3/4" Heel The Lyden Bootie Is An Elevated Take On The Classic Chelsea Boot With A Raised Platform And A Chunky Durable Lug Sole For... more

$157.00

go to store
Free People Shoes | New Free People Bootie Frontier Chelsea Boot Tan Western ~Size Eu 36/Us 5.5 | Color: Cream | Size: 5.5

Free People Shoes | New Free People Bootie Frontier Chelsea Boot Tan Western ~Size Eu 36/Us 5.5 | Color: Cream | Size: 5.5

New Free People Bootie Frontier Chelsea Boot Tan Western ~Size Eu 36/Us 5.5 New Without Box. Please Feel Free To Email With Any Questions. :) more

$70.00

go to store
Coach Shoes | Coach Tia Ankle Chelsea Boots Chunky Heel Wine Color Suede Booties Size 8.5 | Color: Red | Size: 8.5

Coach Shoes | Coach Tia Ankle Chelsea Boots Chunky Heel Wine Color Suede Booties Size 8.5 | Color: Red | Size: 8.5

Coach Tia Ankle Chelsea Boots, Chunky Heels, Wine Color Suede Booties, Size 8.5 Women’s. Preowned. Some Wear From Normal Use, Mainly On The Bottoms. Heel Height Approx 2.5”. Elevate Your Shoe Game With These Stylish Coach Tia Ankle Booties In A... more

$60.00

go to store
Free People Shoes | Chelsea Atlas Bootie By Free People. Nwt | Color: Black/Cream | Size: 8

Free People Shoes | Chelsea Atlas Bootie By Free People. Nwt | Color: Black/Cream | Size: 8

Funky, Textured Bootie By Free People. Patent Leather Toe And Heeled Sections, With Gold Embellishments At The Base. more

$115.00

go to store
Madewell Shoes | Madewell Chelsea Bootie Black Leather | Color: Black | Size: 6

Madewell Shoes | Madewell Chelsea Bootie Black Leather | Color: Black | Size: 6

Worm 3 Times In Great Condition Has No Scuffs On Leather That I Can See. These Are No Longer Available Anywhere I Have Looked. They Are Beautiful. more

$100.00

go to store
Madewell Shoes | Madewell The Grayson Chelsea Boot In Velvet 7 In Distressed Stone / Taupe Bootie | Color: Cream | Size: 7

Madewell Shoes | Madewell The Grayson Chelsea Boot In Velvet 7 In Distressed Stone / Taupe Bootie | Color: Cream | Size: 7

Madewell The Grayson Chelsea Boot In Velvet 7 In Distressed Stone / Taupe Bootie. Preowned With Some Light Bottom Sole Wear In Front, Heels Look Great, Clean, Upper Velvet Area Looks Great No Visible Damage All Of Our Items Have Been Carefully Examined... more

$36.00

go to store
Coach Shoes | Coach Black Snake Skin Leather Patchwork Chelsea Ankle Boots Booties 8.5 | Color: Black | Size: 8.5

Coach Shoes | Coach Black Snake Skin Leather Patchwork Chelsea Ankle Boots Booties 8.5 | Color: Black | Size: 8.5

Coach Snake Skin And Leather Patchwork Chelsea Ankle Boots Size: 8.5 Black Good Used Condition-Flaws Include Some Scrapes Of Normal Wear And Some Fading On The Suede Otherwise In Good Condition Tags: Fall, Autumn, Western Boots, Boots more

$55.00

go to store
Madewell Shoes | Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Bootie | Color: Black | Size: 7

Madewell Shoes | Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Bootie | Color: Black | Size: 7

Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Booties Have Light Scuffs And Distressing But They’re High Quality/Beautifully Made And Have A Lot Of Life Left. more

$38.00

go to store
Madewell Shoes | Madewell Cleary Chelsea Booties, Size 8 | Color: Black | Size: 8

Madewell Shoes | Madewell Cleary Chelsea Booties, Size 8 | Color: Black | Size: 8

Sold Out On Madewell! Step Out This Season In A Classic Chelsea Boot, Made Of Supersmooth Leather. Designed With Durable Rubber Soles And Elastic Insets For Easy On-And-Offs, You'll Want To Wear This Versatile Pair All The Time. And, Cushiness Alert:... more

$35.00

go to store
Kate Spade Shoes | Kate Spade New York Leah Chelsea Block Heel Black Leather Ankle Booties Boots | Color: Black | Size: 9.5

Kate Spade Shoes | Kate Spade New York Leah Chelsea Block Heel Black Leather Ankle Booties Boots | Color: Black | Size: 9.5

Kate Spade New York Leah Chelsea Block Heel Black Leather Ankle Booties Boots. Size 9.5. Pull On Boot. Leather Wrapped Heel. Gold Tone Spade On Back Of Boot 2.5" Block Heel In Very Good Pre-Owned Condition With Slight Signs Of Wear/Slight Wear On... more

$68.00

go to store
Free People Shoes | Free People Atlas Chelsea Booties | Color: Tan | Size: Various

Free People Shoes | Free People Atlas Chelsea Booties | Color: Tan | Size: Various

*New Free People Atlas Chelsea Booties Make A Statement In These So Cool Chelsea Boots Featuring A Soft Suede Design With A Patent Leather Toe And Heel And Edgy Accents. Studded Sole Pull-On Style Elastic Side Accents Platform: 1.5 In Shaft: 6 In... more

$109.00

go to store
Free People Shoes | Free People Atlas Chelsea Booties | Color: Red | Size: Various

Free People Shoes | Free People Atlas Chelsea Booties | Color: Red | Size: Various

*New Free People Atlas Chelsea Booties Make A Statement In These So Cool Chelsea Boots Featuring A Soft Suede Design With A Patent Leather Toe And Heel And Edgy Accents. Studded Sole Pull-On Style Elastic Side Accents Platform: 1.5 In Shaft: 6 In... more

$124.00

go to store
Free People Shoes | Free People James Chelsea Boot Booties Size 40 10 Deep Khaki Leather New | Color: Brown | Size: 40eu

Free People Shoes | Free People James Chelsea Boot Booties Size 40 10 Deep Khaki Leather New | Color: Brown | Size: 40eu

New In Box A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore Insets At The Sides.Side Zip Closure Cushioned Insole Leather Upper And Lining/Rubber Sole Made In Spain Women's Shoes... more

$129.00

go to store
J. Crew Shoes | J. Crew Chelsea Bootie Us W 8 | Color: Brown | Size: 8

J. Crew Shoes | J. Crew Chelsea Bootie Us W 8 | Color: Brown | Size: 8

J. Crew Chelsea Bootie Color: Brownstone Size: 8 Lightly Worn more

$125.00

go to store
Coach Shoes | Coach Alexa White Platform Leather Heeled Chelsea Booties | Color: White | Size: 8

Coach Shoes | Coach Alexa White Platform Leather Heeled Chelsea Booties | Color: White | Size: 8

White Platform Alexa Leather Heeled Chelsea Coach Size 8 Brand New Never Been Worn more

$200.00

go to store
Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: Black | Size: 8

Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: Black | Size: 8

Reposhing This Item I Purchased From @Pinetreeposh. Loved It, But They Are Too Small I’m Usually A 9 Or 9.5. These Fit So Snug, I Would Compare Them To An 8, Maybe An 8.5. more

$100.00

go to store
Madewell Shoes | Madewell Carina Ankle Chelsea Boot Bootie | Color: Brown | Size: 7

Madewell Shoes | Madewell Carina Ankle Chelsea Boot Bootie | Color: Brown | Size: 7

Excellent Condition! Size 7 Cognac Color more

$85.00

go to store
Madewell Shoes | Madewell Grayson Brogue Chelsea Boot Ivory Size 6.5 Suede Booties Western Boot | Color: Cream | Size: 6.5

Madewell Shoes | Madewell Grayson Brogue Chelsea Boot Ivory Size 6.5 Suede Booties Western Boot | Color: Cream | Size: 6.5

Brand: Madewell Size: 6.5 Color: Ivory Material: Suede Upper Condition: Good Used Condition, Gentle Wear/Rub On Suede- View Pictures Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforationsand Cut... more

$45.00

go to store
Coach Shoes | Coach X Tabitha Simmons Chelsea Hiker Booties | Color: Black | Size: Various

Coach Shoes | Coach X Tabitha Simmons Chelsea Hiker Booties | Color: Black | Size: Various

Coach X Tabitha Simmons Chelsea Hiker Booties Size 6 Velvet Upper Man-Made Leather Lining And Footbed Rubber Outsole Zip Closure Shaft: 4 1/2" Height, 9" Circumference 1" Heel Coach X Tabitha Simmons more

$159.00

go to store
Madewell Shoes | Nib Madewell Sonia Low Chelsea Western Ankle Bootie Snake Embossed Leather 8 | Color: Black/Tan | Size: 8

Madewell Shoes | Nib Madewell Sonia Low Chelsea Western Ankle Bootie Snake Embossed Leather 8 | Color: Black/Tan | Size: 8

Nib Madewell Sonia Low Chelsea Western Ankle Bootie Snake Embossed Leather Condition: New In Box Size: Women’s Us 8 Color: Heather Natural Multi :: Orders Are Shipped The Same Or The Next Business Day Excluding Sat & Sun. Mq-2111-003/2275 more

$72.00

go to store
J. Crew Shoes | J.Crew Leather Chelsea Western Bootie | Color: Black | Size: 11

J. Crew Shoes | J.Crew Leather Chelsea Western Bootie | Color: Black | Size: 11

More Photos Coming Soon -Good Condition -Leather Lining -Cushioned Footbed -Stacked Heel -Synthetic Outsole -Heel Height: 2 34 In -Shaft: 6.5" -Imported more

$88.00

go to store
Madewell Shoes | Ainsley Chelsea Golf Leather Booties From Madewell. | Color: Gold | Size: 7.5

Madewell Shoes | Ainsley Chelsea Golf Leather Booties From Madewell. | Color: Gold | Size: 7.5

Gently Worn Gold Leather Madewell Booties. Crafted From Metallic Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Leather. 4" Shaft Height (Based On Size 7). 1 3/16" Heel. Metallic Leather Upper. Leather Lining.... more

$75.00

go to store
Madewell Shoes | Madewell Booties Bryce Suede Leather Chelsea Ankle Black Size 10 Style M4674 | Color: Black | Size: 10

Madewell Shoes | Madewell Booties Bryce Suede Leather Chelsea Ankle Black Size 10 Style M4674 | Color: Black | Size: 10

Madewell Booties Bryce Suede Leather Chelsea Ankle Black Size 10 Style M4674. Madewell Bryce Ankle Boots Booties Black Suede Leather M4674 Side Zip Biker Westernexcellent Condition more

$59.00

go to store
Free People Shoes | Free People Size 9 (Eu 39) Black Essential Chelsea Boots Zip Back Bootie New | Color: Black | Size: 9

Free People Shoes | Free People Size 9 (Eu 39) Black Essential Chelsea Boots Zip Back Bootie New | Color: Black | Size: 9

This Item Is New Without Tags. Please See Pictures For Measurements. Please Reach Out If You Are Unsatisfied With Your Purchase In Any Way. I Strive To Provide Excellent Customer Service. Thank You For Supporting My Small Business! more

$114.00

go to store
Free People Shoes | Free People Shadow Lark Cure Blue Leather Ankle Chelsea Bootie Sz 6 | Color: Blue | Size: 6

Free People Shoes | Free People Shadow Lark Cure Blue Leather Ankle Chelsea Bootie Sz 6 | Color: Blue | Size: 6

Free People Shadow Lark Ankle Chelsea Bootie Sz 6 Navy Perforated Leather Hidden Snaps On One Side Side Zipper On Other Side Ankle Boots, Chelsea Style Small Heel Cute Stitched Detail On Side Size 36 Pre-Owned Have Some Wear But Still Lots Of Left... more

$45.00

go to store

More information about Men's Shoes

Best prices on Sierra chelsea bootie in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.