Top Picks

GEMMA’S PICK
MISSPAPBrunello Cucinelli Women's Preloved Chelsea Kitten-Heeled Ankle Boots Burgundy Leather
£292.00 MISSPAP

LEANNE’S PICK
DOROTHY PERKINSInfinity Leather Tamaris Bordeaux Leather Chelsea Ankle Boots In Burgundy
£104.64
£89.99 DOROTHY PERKINS

£95.00 DOROTHY PERKINS

£30.94
£25.99 DOROTHY PERKINS
How we pick
These picks came from Gemma, Imogen, Leanne, Esme and Freya, who each chose the one they'd happily wear themselves. That's the whole test really. Would we buy it, would we wear it more than once, and does it look like the photo once it arrives? We skip anything that looks cheap up close, cap how many pieces come from any one shop, and keep the list fresh as stock changes. We earn a small commission if you buy through our links, it never costs you more, and it never decides what gets picked.
Under £506 pieces

BLACKS
Women’s Original Chelsea Wellington Boots
£44.97 BLACKS−16%

DOROTHY PERKINS
Ajvani Low Heel Chelsea Ankle Boots Wellingtons Wellies In Burgundy
£30.94 £25.99 DOROTHY PERKINS−36%

DOROTHY PERKINS
Ajvani Flat Heel Brogue Chelsea Ankle Boots In Burgundy
£54.67 £34.99 DOROTHY PERKINS−33%

DOROTHY PERKINS
Ajvani Low Heel Pull On Brogue Ankle Chelsea Boots In Burgundy
£55.21 £36.99 DOROTHY PERKINS
DOROTHY PERKINS
Ravel Dark Bordo Leather 'bray' Ankle Boots In Burgundy
£95.00 DOROTHY PERKINS−14%

DOROTHY PERKINS
Infinity Leather Tamaris Bordeaux Leather Chelsea Ankle Boots In Burgundy
£104.64 £89.99 DOROTHY PERKINSWorth the splurge3 pieces

MISSPAP
Brunello Cucinelli Women's Preloved Chelsea Kitten-Heeled Ankle Boots Burgundy Leather
£292.00 MISSPAP−35%

OFFICE SHOES
Vagabond Womens Dorah Chelsea Boots Dark Bordo Brown
£153.85 £100.00 OFFICE SHOES−22%

DOROTHY PERKINS
Infinity Leather Fly London Red Hely268 Chelsea Leather Ankle Pull-On Platform Comfort Boots In Burgundy
£173.06 £134.99 DOROTHY PERKINSMore like this
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