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    Best Seller
    Free People Shoes | Free People White Jackson West Pointed Toe Block Heel Ankle Boots 39 9 Western | Color: Black/White | Size: 9

    Free People Shoes | Free People White Jackson West Pointed Toe Block Heel Ankle Boots 39 9 Western | Color: Black/White | Size: 9

    In Excellent Preowned Condition Free People Western Booties. Tagged Size 39, Us Size 9. Made Of Portugal. Channel Your Inner Cowgirl Whenever You Slip On This Pair Of Pointed-Toe Boots Crafted From Durable Leather That'll Take You From The Countryside... more

    $120.00

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    Zara Shoes | New!! Zara Black Stretch Faux Leather Heeled Square Toe Ankle Boots | Color: Black | Size: 39

    Zara Shoes | New!! Zara Black Stretch Faux Leather Heeled Square Toe Ankle Boots | Color: Black | Size: 39

    Edgy Square Toe / Square Heel Sock Boots From Zara Made From A Classic Black Stretch Vegan Leather Eu Size 39 , Heel: 4" more

    $79.00

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    Best Seller
    Madewell Shoes | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

    Madewell Shoes | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

    Madewell 9.5 Spencer Short Chelsea Boot Style C1375 Mink Taupe Tan Color Stacked Heel No Original Box Slight Marks In Leather (See Photos) Excellent Used Condition 1.75" Heel Almond Toe Luxe Quality Stretch On Both Sides Offers Welcome. No Trades. more

    $36.00

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    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 12

    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 12

    - Upper: Leather, Textile. - Lining: Textile. - Outsole: TPR. - Fastening: D-Ring, Inside Zip, Stretch Lace. - 5 Eyelets. - Leather Sock, Memory Foam Sock. - Low Heel. - Design: Textured. - Packaging: Boxed.. - Gender: Men more

    $95.99 $73.70

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    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 9

    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 9

    - Upper: Leather, Textile. - Lining: Textile. - Outsole: TPR. - Fastening: D-Ring, Inside Zip, Stretch Lace. - 5 Eyelets. - Leather Sock, Memory Foam Sock. - Low Heel. - Design: Textured. - Packaging: Boxed.. - Gender: Men more

    $95.99 $73.70

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    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 8

    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 8

    - Upper: Leather, Textile. - Lining: Textile. - Outsole: TPR. - Fastening: D-Ring, Inside Zip, Stretch Lace. - 5 Eyelets. - Leather Sock, Memory Foam Sock. - Low Heel. - Design: Textured. - Packaging: Boxed.. - Gender: Men more

    $95.99 $73.70

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    Burberry Shoes | Burberry Hurr Ankle Leather Stretch Boots (41.5) | Color: Black | Size: 41.5

    Burberry Shoes | Burberry Hurr Ankle Leather Stretch Boots (41.5) | Color: Black | Size: 41.5

    Dimensions: Heel: 4.5cm 100% Polyurethane, 70% Calf Leather, 30% Lambskin Leather, Lining: 100% Lambskin Leather Made In Italy Designer Colour: A1189 more

    $980.00

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    Madewell Shoes | Madewell The Justine Ankle Leather Boot | Color: Black | Size: 8

    Madewell Shoes | Madewell The Justine Ankle Leather Boot | Color: Black | Size: 8

    Excellent Like New Condition. Stunning Boots! So Comfortable, Genuine Leather. With A Chic Pointed Toe, Stretchy Back And Modern Sculpted Heel, These Leather Ankle Boots Makes A Subtle Statement Paired With Everything From A Swishy Maxi To Structured... more

    $180.00

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    Madewell Shoes | Madewell The Western Heeled Ankle Boot Pull On Pointed Toe Leather Suede Sz 7.5 | Color: Cream | Size: 7.5

    Madewell Shoes | Madewell The Western Heeled Ankle Boot Pull On Pointed Toe Leather Suede Sz 7.5 | Color: Cream | Size: 7.5

    With Classic Western Stitching And A Comfy Stacked Heel, This Supple Suede Ankle Boot Is The Cutest (And Goes With Any And Everything). The Pull Tab And Covered Elastic Inserts Make Taking Them On And Off A Total Breeze. Crafted From Smooth Leather... more

    $64.00

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    J. Crew Shoes | J. Crew Leather High-Shaft Stacked-Heel Boots Rich Caramel Jcrew 10 | Color: Brown/Tan | Size: 10

    J. Crew Shoes | J. Crew Leather High-Shaft Stacked-Heel Boots Rich Caramel Jcrew 10 | Color: Brown/Tan | Size: 10

    New In Box! Never Worn, Tried On Once And Did Not Fit. Color: Rich Caramel A Modern Update To Your Go-To Fall Shoes, These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite... more

    $120.00

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    J. Crew Shoes | J.Crew $248 Leather High-Shaft Stacked-Heel Boots,Rich Caramel Size 8,New | Color: Brown/Tan | Size: 8

    J. Crew Shoes | J.Crew $248 Leather High-Shaft Stacked-Heel Boots,Rich Caramel Size 8,New | Color: Brown/Tan | Size: 8

    A Modern Update To Your Go-To Fall Shoes, These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite Straight-Leg Jeans. Detail We Love: Stretchy Side Panels Make Them Easier To... more

    $79.00

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    J. Crew Shoes | J Crew Leather High-Shaft Stacked Heel Boots In Rich Caramel Size 7 | Color: Red | Size: 7

    J. Crew Shoes | J Crew Leather High-Shaft Stacked Heel Boots In Rich Caramel Size 7 | Color: Red | Size: 7

    J Crew Leather High-Shaft Stacked Heel Boots In Rich Caramel Size 7 A Modern Update To Your Go-To Fall Shoes. These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite... more

    $70.00

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    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite Straight- Leg Jeans. Detail We Love: Stretchy Side Panels Make Them Easier To Take On And Off. Leather Upper And Lining.... more

    $50.00

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    J. Crew Shoes | J Crew Leather High Shaft Stacked Heel Boots In Black Size 9 Modern Fall Shoes | Color: Black | Size: 9

    J. Crew Shoes | J Crew Leather High Shaft Stacked Heel Boots In Black Size 9 Modern Fall Shoes | Color: Black | Size: 9

    Approximate Heel Height: 2” A Modern Update To Your Go-To Fall Shoes, These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite Straight-Leg Jeans. Detail You’ll Love: Stretchy... more

    $119.00

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    J. Crew Shoes | J. Crew Black Leather High-Shaft Stacked-Heel Boots 8.5 | Color: Black | Size: 8.5

    J. Crew Shoes | J. Crew Black Leather High-Shaft Stacked-Heel Boots 8.5 | Color: Black | Size: 8.5

    J. Crew Leather High-Shaft Stacked-Heel Boots Size 8.5 These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite Straight-Leg Jeans. Detail We Love: Stretchy Side Panels Make... more

    $119.00

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    Gucci Shoes | Gucci 'Gg' Ankle Boots | Color: Black | Size: Various

    Gucci Shoes | Gucci 'Gg' Ankle Boots | Color: Black | Size: Various

    White Leather Ankle Boots With Black Stretch 'Gg' Jersey Insert, Leather Loop At The Back, Logo Detail On The Heel And A Rubber Sole. Color: White/Black Size & Fit: Uk Men Composition: 100% Leather Sku: Jul-718713aaa8l9059 Welcome To The Official... more

    $1,207.00

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    Gucci Shoes | Gucci Ankle Boots | Color: Black | Size: 8

    Gucci Shoes | Gucci Ankle Boots | Color: Black | Size: 8

    Vintage Black Gucci Ankle Boots. Leather Lining, Stretchy Fabric Exterior, 2.5” Heel, Size 38c, In Excellent Condition, Priced To Sell! more

    $275.00

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    Coach Shoes | Coach Suffolk Calf Suede Ankle Boots In Mink | Color: Brown | Size: Various

    Coach Shoes | Coach Suffolk Calf Suede Ankle Boots In Mink | Color: Brown | Size: Various

    New In Box, Coach Suffolk Gorgeous Brown Suede Ankle Boots. Stretch Goring And A Pull-Loop Make It Easy To Get On & Off. Heel Height 1 1/4". Leather Upper, Footbed And Sole. more

    $64.00

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    Free People Shoes | Free People Arlo Ankle Boots | Color: Gray/Green | Size: Various

    Free People Shoes | Free People Arlo Ankle Boots | Color: Gray/Green | Size: Various

    An Essential In Any Boot Collection, These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. * Minimal Heel * Cushioned Insole * Durable... more

    $130.00

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    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    An Essential In Any Boot Collection, These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. * Minimal Heel * Cushioned Insole * Durable... more

    $120.00

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    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    An Essential In Any Boot Collection, These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. * Minimal Heel * Cushioned Insole * Durable... more

    $130.00

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    Free People Shoes | Free People: Arlo Ankle Boots In Tan | Color: Brown | Size: 7

    Free People Shoes | Free People: Arlo Ankle Boots In Tan | Color: Brown | Size: 7

    Free People Size 37 Us 7m These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. Minimal Heel Cushioned Insole Durable Outsole more

    $160.00

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    Michael Kors Shoes | Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel 9 | Color: Cream/Tan | Size: 9

    Michael Kors Shoes | Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel 9 | Color: Cream/Tan | Size: 9

    Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel Size 9 A Sharply Bootie Fashioned From Smooth ,Burnished Black Leather Dials Up The Chic Appeal Of Your Daily Style, While Logo-Etched Hardware Flashes At The Heel For A Signature... more

    $20.00

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    Burberry Shoes | Burberry Prorsum Stretch Mesh Ankle Sock Boots | Color: Black | Size: 6

    Burberry Shoes | Burberry Prorsum Stretch Mesh Ankle Sock Boots | Color: Black | Size: 6

    Burberry Prorsum Sheer Mesh Ankle Boots With Chunky Black Lacquered Zip At The Back. Mesh W Leather Insole. 1.18 Inches Platform; 5.118 Inches Heel. In Excellent, Worn One Evening Condition. This Is From Burberry S Higher End Runway Line. I Bought It W... more

    $340.00

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    Torrid Shoes | Leather Boots | Color: Black | Size: 10w

    Torrid Shoes | Leather Boots | Color: Black | Size: 10w

    Ankle Height Leather Boots With A Faux Buckle Strap And Elastic In The Back For Stretch. Brand New.... Never Worn. more

    $30.00

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    Michael Kors Shoes | Hamilton Stretch Leather Boot | Color: Brown | Size: 6.5

    Michael Kors Shoes | Hamilton Stretch Leather Boot | Color: Brown | Size: 6.5

    Ankle Boot Vachetta Leather/Stretch Panel 100% Leather Lining: Synthetic Sole: Rubber Almond Toe Zip Fastening Heel Height: 2" Heel Type: Stacked Imported more

    $75.00

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    Free People Shoes | Free People Jackson West Leather Boot | Color: Gold | Size: 6

    Free People Shoes | Free People Jackson West Leather Boot | Color: Gold | Size: 6

    Pointed Toe All-Over Textured Leather Construction Stretch-Knit Gored Ankle Panel Zigzagged Stitch Stretch Topline Stacked Block Heel Approx. 4.75” Shaft Height, 8.5” Opening Circumference. Approx. 3.25” Heel Height more

    $129.00

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    Kate Spade Shoes | Euc Kate Spade Leather Boots | Color: Black/Brown | Size: 8.5

    Kate Spade Shoes | Euc Kate Spade Leather Boots | Color: Black/Brown | Size: 8.5

    Kate Spade Boots. Very Versatile Front Panel In Rich Chocolate Brown With Black Stretch Material In Back. Little Leather Bows With Gold Studs On Outside Ankle. Some Scuffs On The Toe Shown In Photos. Very Comfortable Stretch Calf, Low Flat Heel,... more

    $50.00

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    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown Size 8 Nwt From Marshall’s Cognac Brown Caramel Embossed Leather Upper Croc Back Zipper Closure Approx 1.5” Heel Stretchy Top Half Mixed Media Ankle Length more

    $100.00

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    Nine West Shoes | Black Sandal Boots-New! | Color: Black | Size: 8.5

    Nine West Shoes | Black Sandal Boots-New! | Color: Black | Size: 8.5

    Stylish Ankle Boot With Stiletto Heel Elastic Straps For Stretch And Comfort more

    $25.00

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    Gucci Shoes | Gorgeous Men's Gucci Boots | Color: Black | Size: 11

    Gucci Shoes | Gorgeous Men's Gucci Boots | Color: Black | Size: 11

    Description: - Gucci Leather Ankle Chelsea Boots - Smooth Black Leather - Comfort Stretch Panel - Pull On Loop - Square-Toes - 1" Heel - Lesther Insoles - Tan Soles With "Gucci" Script - Made In Italy Fit: Boots By Gucci Typically Fit True To Size.... more

    $260.00

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    Free People Shoes | Free People Vegan Oakland Over-The-Knee Boot | Color: Black | Size: 10

    Free People Shoes | Free People Vegan Oakland Over-The-Knee Boot | Color: Black | Size: 10

    Sleek Vegan Leather Boots With Body Hugging Over-The-Knee Design With Chunky Platform Heel Half-Zip Ankle Closure Stretch Fit Lined Interior Cushioned Insole *Measurements* Shaft - 23.5 In Heel - 4.5 In Platform - 1.5 In Worn Twice, Like New Very... more

    $50.00

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    Ralph Lauren Shoes | - Ralph Lauren Riding Boot | Color: Black/Brown | Size: 9.5

    Ralph Lauren Shoes | - Ralph Lauren Riding Boot | Color: Black/Brown | Size: 9.5

    Leather Upper Decorative Harness Strap With Chainlink Detail 14½" Shaft Height, Inside Zipper 14½" Calf Circumference, Inside Topline Elastic Insert For Stretch Fit Round Toe Padded Fabric Lining 1¼" Stacked Block Heel Leather Has Some Scratches But... more

    $110.00

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    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Nib Free People James Chelsea Ankle Boots Side Zip Closure Stretch Side Panels For Easy On Cushion Footbed Color Is White But Looks More Like A Cream Color Leather Uppers 6” Shaft Height 3.5” Chunky Heel 1” Platform more

    $85.00

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    Free People Shoes | Free People Tan Suede Boots. Size 40. Preloved, Great Condition. | Color: Tan | Size: 40

    Free People Shoes | Free People Tan Suede Boots. Size 40. Preloved, Great Condition. | Color: Tan | Size: 40

    Free People Tan Suede Boots. Size 40. Preloved, Great Condition. Inside Zipper With Suede Pull Tab. The Shaft Hits Between Ankle And Calf. Elastic Band Hidden At The Top For Some Stretch. Real Leather Upper, Wooden Sole. 3” Heel. Small Little Stain On... more

    $40.00

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    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 7

    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 7

    - Upper: Leather, Textile. - Lining: Textile. - Outsole: TPR. - Fastening: D-Ring, Inside Zip, Stretch Lace. - 5 Eyelets. - Leather Sock, Memory Foam Sock. - Low Heel. - Design: Textured. - Packaging: Boxed.. - Gender: Men more

    $95.99 $73.70

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    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 11

    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 11

    - Upper: Leather, Textile. - Lining: Textile. - Outsole: TPR. - Fastening: D-Ring, Inside Zip, Stretch Lace. - 5 Eyelets. - Leather Sock, Memory Foam Sock. - Low Heel. - Design: Textured. - Packaging: Boxed.. - Gender: Men more

    $95.99 $73.70

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    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 10

    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 10

    - Upper: Leather, Textile. - Lining: Textile. - Outsole: TPR. - Fastening: D-Ring, Inside Zip, Stretch Lace. - 5 Eyelets. - Leather Sock, Memory Foam Sock. - Low Heel. - Design: Textured. - Packaging: Boxed.. - Gender: Men more

    $95.99 $73.70

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    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 13

    Roamers Mens Herringbone Leather Ankle Boots (Tan) - Brown - 13

    - Upper: Leather, Textile. - Lining: Textile. - Outsole: TPR. - Fastening: D-Ring, Inside Zip, Stretch Lace. - 5 Eyelets. - Leather Sock, Memory Foam Sock. - Low Heel. - Design: Textured. - Packaging: Boxed.. - Gender: Men more

    $95.99 $73.70

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    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Blue - 12

    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

    $69.99

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    More information about Men's Shoes

    Best prices on Carmen leather ankle strap heels, Stretchable, Boots 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.