Top Picks
Women's boots Be Lenka Entice Neo
DANI’S PICK MADE IN PARADISWomen's boots Be Lenka Entice Neo
£83.31 MADE IN PARADIS
Women's Chelsea boots Tamaris 1-25403-43
LAUREN’S PICK MADE IN PARADISWomen's Chelsea boots Tamaris 1-25403-43
£84.57 MADE IN PARADIS
TOMS Womens Bennet Chelsea Faux Fur Lined Boots Oak Brown
TAMSIN’S PICK OFFICE SHOESTOMS Womens Bennet Chelsea Faux Fur Lined Boots Oak Brown
£125.00 £55.00 OFFICE SHOES
Womens Flat Chelsea Boots Tamaris 1-25498-41
HANNAH’S PICK SNEAKINWomens Flat Chelsea Boots Tamaris 1-25498-41
£101.49 SNEAKIN
Women's Heeled Chelsea Boots Tamaris 1-25026-41
AISHA’S PICK SNEAKINWomen's Heeled Chelsea Boots Tamaris 1-25026-41
£76.11 SNEAKIN
How we pick

Nobody here is paid to push a brand. Dani, Lauren, Tamsin, Hannah and Aisha went through everything in winter chelsea boots the way you would on a lunch break, scrolling, squinting at the fabric, checking the price twice. What made the list is what they'd actually put in their own basket. We look for pieces that wash well, sit right and don't cost silly money for what they are, and we mix up the shops so you're not just looking at one high street name over and over. Prices and stock come straight from the retailers and change often, so it's always worth a quick check before you buy.

Under £508 pieces
Jumpers Amara Reya Buttercup cable knit jumper in Anthracite
TOKYO LAUNDRY

Jumpers Amara Reya Buttercup cable knit jumper in Anthracite

£9.99 TOKYO LAUNDRY
Jumpers Bate Wool Rich Knitted Jumper in Teal
TOKYO LAUNDRY

Jumpers Bate Wool Rich Knitted Jumper in Teal

£24.99 TOKYO LAUNDRY
−25%Ivachy Women Ankle Chelsea Boots In Black
DOROTHY PERKINS

Ivachy Women Ankle Chelsea Boots In Black

£39.00 £29.25 DOROTHY PERKINS
−53%Xy London 'karev' Black Ankle Boots Pull On Elasticated Gusset Chelsea In Jet Black
DOROTHY PERKINS

Xy London 'karev' Black Ankle Boots Pull On Elasticated Gusset Chelsea In Jet Black

£70.19 £32.99 DOROTHY PERKINS
−53%Xy London 'karev' Black Ankle Boots Pull On Elasticated Gusset Chelsea
DOROTHY PERKINS

Xy London 'karev' Black Ankle Boots Pull On Elasticated Gusset Chelsea

£70.19 £32.99 DOROTHY PERKINS
−28%Ajvani Low Wedge Heel Comfort Ankle Faux Leather Chelsea Boots In Black
DOROTHY PERKINS

Ajvani Low Wedge Heel Comfort Ankle Faux Leather Chelsea Boots In Black

£49.99 £35.99 DOROTHY PERKINS
−28%Ajvani Low Wedge Heel Comfort Ankle Faux Leather Chelsea Boots In Brown
DOROTHY PERKINS

Ajvani Low Wedge Heel Comfort Ankle Faux Leather Chelsea Boots In Brown

£49.99 £35.99 DOROTHY PERKINS
−50%OFFICE Womens Adeline Square Toe Chelsea Boots Black Leather
OFFICE SHOES

OFFICE Womens Adeline Square Toe Chelsea Boots Black Leather

£90.00 £45.00 OFFICE SHOES
£50 to £10011 pieces
OFFICE Womens Amber Chunky Chelsea Ankle Boots Black Leather
OFFICE SHOES

OFFICE Womens Amber Chunky Chelsea Ankle Boots Black Leather

£80.00 OFFICE SHOES
Women's boots Be Lenka Entice Neo
MADE IN PARADIS

Women's boots Be Lenka Entice Neo

£83.31 MADE IN PARADIS
Women's heeled boots Tamaris 1-25026-41
SNEAKIN

Women's heeled boots Tamaris 1-25026-41

£76.11 SNEAKIN
Flat ankle boots for women Tamaris 1-25448-45
SNEAKIN

Flat ankle boots for women Tamaris 1-25448-45

£84.57 SNEAKIN
Women's Chelsea boots Tamaris 1-25403-43
MADE IN PARADIS

Women's Chelsea boots Tamaris 1-25403-43

£84.57 MADE IN PARADIS
Flat ankle boots for women Tamaris 1-25483-45
MADE IN PARADIS

Flat ankle boots for women Tamaris 1-25483-45

£67.65 MADE IN PARADIS
Women's Heeled Chelsea Boots Tamaris 1-25026-41
SNEAKIN

Women's Heeled Chelsea Boots Tamaris 1-25026-41

£76.11 SNEAKIN
Women's Chelsea boots Tamaris 1-25483-45
SNEAKIN

Women's Chelsea boots Tamaris 1-25483-45

£67.65 SNEAKIN
−56%TOMS Womens Bennet Chelsea Faux Fur Lined Boots Oak Brown
OFFICE SHOES

TOMS Womens Bennet Chelsea Faux Fur Lined Boots Oak Brown

£125.00 £55.00 OFFICE SHOES
−40%Debenhams Black Wool Blend Epsom Coat
DOROTHY PERKINS

Debenhams Black Wool Blend Epsom Coat

£120.00 £72.00 DOROTHY PERKINS
−40%Debenhams Men's Black Wool Blend Epsom Coat
MISSPAP

Debenhams Men's Black Wool Blend Epsom Coat

£120.00 £72.00 MISSPAP
Worth the splurge6 pieces
Dr. Martens Womens 2976 Bex Chelsea Boots Black Milled Nubuck
OFFICE SHOES

Dr. Martens Womens 2976 Bex Chelsea Boots Black Milled Nubuck

£190.00 OFFICE SHOES
Women's rain boots Ariat Wexford Sherpa
SNEAKIN

Women's rain boots Ariat Wexford Sherpa

£163.71 SNEAKIN
Women's Chelsea boots Balagan Arava
SNEAKIN

Women's Chelsea boots Balagan Arava

£160.08 SNEAKIN
Womens Flat Chelsea Boots Tamaris 1-25498-41
SNEAKIN

Womens Flat Chelsea Boots Tamaris 1-25498-41

£101.49 SNEAKIN
−31%Timberland Womens Lyonsdale Chelsea Boots Black Nubuck
OFFICE SHOES

Timberland Womens Lyonsdale Chelsea Boots Black Nubuck

£144.93 £100.00 OFFICE SHOES
−21%Dr. Martens Womens 2976 Bex Chelsea Boots Gunmetal Milled Nubuck Grey
OFFICE SHOES

Dr. Martens Womens 2976 Bex Chelsea Boots Gunmetal Milled Nubuck Grey

£189.87 £150.00 OFFICE SHOES

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