Women's Chelsea under $300



Frye Wheat

Brand: Frye
Color: Wheat
An almond-toe Chelsea boot handmade from supple buffalo leather gets a cowgirl twist from Western-inspired seaming and stitching and a utilitarian pull tab in back.

Italeau Nero Leather

Brand: Italeau
Color: Nero Leather
A slim, shapely bootie with a softly pointed toe is handcrafted in Italy from supple, waterproofed leather in a Chelsea-inspired silhouette.

L'Autre Chose Black

Brand: L'Autre Chose
Color: Black
A high-style reimagining of the classic-cool chelsea boot, this statement pair from L'Autre Chose features gilded leather insets. Black leather upper with gold leather accordion side panels, pointed toe, back pull-on tab, chunky Cuban heel.

Hogan Brown

Brand: Hogan
Color: Brown
Hogan's mid-brown suede Chelsea boots are a versatile pair that you can rely on season after season. Brown suede, round toe, elasticated insert, contrast trim, leather insole and rubber sole.

Frye Wine

Brand: Frye
Color: Wine
A logo-embossed button details the pull tab of a refined Chelsea boot bench-crafted by hand from richly burnished leather.

Hispanitas Bordo Leather

Brand: Hispanitas
Color: Bordo Leather
Painterly hash marks bring color and geometry to a soft leather Chelsea bootie styled with an elegant almond toe and a wrapped block heel

Frye Slate Brown

Brand: Frye
Color: Slate Brown
A logo-embossed button adorns the single pull tab of a classic Chelsea boot bench-crafted by hand from richly burnished leather.

Frye Black

Brand: Frye
Color: Black
Frye Women's Melissa Leather Chelsea Booties

Alberto Fermani Terra

Brand: Alberto Fermani
Color: Terra
Playfully extending the Chelsea silhouette, this suede platform boot puts a modern spin on a cool classic.

Frye Black

Brand: Frye
Color: Black
Side zips put a fresh twist on the classic Chelsea detailing of this richly burnished leather boot.

Frye Company Cognac

Brand: Frye Company
Color: Cognac
This heritage-inspired hand-crafted Chelsea boot delivers the superior style that can only come from Frye. Soft vegetable-tanned Italian leather upper.

Cole Haan Brandy Brown Leather

Brand: Cole Haan
Color: Brandy Brown Leather
Elastic-gore insets define the classic Chelsea silhouette of a downtown-chic boot crafted from waterproof leather. Cole Haan's innovative Grand.

Italeau Daino Leather

Brand: Italeau
Color: Daino Leather
A slim, shapely bootie with a softly pointed toe is handcrafted in Italy from supple, waterproofed leather in a Chelsea-inspired silhouette.

Alberto Fermani Travertine

Brand: Alberto Fermani
Color: Travertine
Alberto Fermani reimagines the Chelsea bootie with this version featuring concealed V-cut goring notched into the topline and a lightly flared demi-block heel providing beautifully sculpted lift.

Frye Wine

Brand: Frye
Color: Wine
Frye Women's Melissa Chelsea Boots Women's Shoes

Stuart Weitzman Black

Brand: Stuart Weitzman
Color: Black
Chelsea-inspired ankle boot in supple leather. Stacked heel, 1.

Frye Company Black

Brand: Frye Company
Color: Black
This heritage-inspired hand-crafted Chelsea boot delivers the superior style that can only come from Frye. Soft vegetable-tanned Italian leather upper.

Eileen Fisher Black Washed Leather

Brand: Eileen Fisher
Color: Black Washed Leather
A chunky wedge heel and articulated treads add a no-nonsense vibe to a sturdy Chelsea bootie made with a stretchy elastic inset that wraps all the way around the back for a comfy fit.

Frye Cognac

Brand: Frye
Color: Cognac
Side zips put a fresh twist on the classic Chelsea detailing of this richly burnished leather boot.

Frye Black

Brand: Frye
Color: Black
A logo-embossed button adorns the single pull tab of a classic Chelsea boot bench-crafted by hand from richly burnished leather.

H by Hudson Metallic Blue

Brand: H by Hudson
Color: Metallic Blue
A sleek bootie with classic Chelsea detailing goes fashion-forward with an upper made from crinkled leather in a shimmery metallic blue hue.

Hogan Black

Brand: Hogan
Color: Black
Hogan's jet black patent leather Chelsea boots are a dressed up that you can rely on season after season. Black patent leather, round toe, elasticated insert, contrast trim, leather insole and rubber sole.