Taupe hoodie, blue trousers & Chelsea boots
€985*For mild days, about 12–20°C · Outdoors · 4 pieces from €130*
Would you wear it?
What to wear with Chelsea boots
Chelsea boot outfits with slim jeans, trousers and knits, smart enough for the office. 21 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026
21 looks
Navy jumper, trousers & brown suede boots
€189*For cool days, about 5–12°C · Smart casual · 3 pieces from €19*
Would you wear it?
Grey sweatshirt, blue jeans & Chelsea boots
€813*For mild days, about 12–20°C · Weekend · 4 pieces from €139*
Would you wear it?
Black puffer jacket, green sweatshirt & jeans
€537*For cool days, about 5–12°C · Weekend · 4 pieces from €100*
Would you wear it?
Black jacket, black jumper & jeans
€630*For cool days, about 5–12°C · Everyday · 5 pieces from €80*
Striped jumper, trousers & brown suede boots
€547*For cool days, about 5–12°C · Everyday · 3 pieces from €100*
Grey wool coat, green jumper & black cargo trousers
€890*For cold days, about −5 to 5°C · Smart casual · 5 pieces from €100*
Grey jacket, blue jumper & trousers
€922*For cool days, about 5–12°C · Everyday · 4 pieces from €100*
Polo, trousers & Chelsea boots
€649*For mild days, about 12–20°C · Smart casual · 3 pieces from €35*
Top, blue jeans & Chelsea boots
€610*For mild days, about 12–20°C · Weekend · 3 pieces from €115*
Striped polo, white shorts & Chelsea boots
€640*For warm days, about 20–30°C · Outdoors · 4 pieces from €125*
Brown sweatshirt, white shorts & Chelsea boots
€893*For mild days, about 12–20°C · Weekend · 4 pieces from €53*