


Red sweatshirt, wide-leg jeans & Chelsea boots
£181*For cool days, about 5–12°C · Outdoors · 3 pieces from £35*
Chelsea boot outfits with slim jeans, trousers and knits, smart enough for the office. 49 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026
49 looks
For mild days, about 12–20°C · Outdoors · 4 pieces from £29*
For mild days, about 12–20°C · Weekend · 3 pieces from £50*
For cool days, about 5–12°C · Outdoors · 3 pieces from £55*
For mild days, about 12–20°C · Outdoors · 4 pieces from £19*
For cool days, about 5–12°C · Weekend · 4 pieces from £29*
For mild days, about 12–20°C · Active · 3 pieces from £30*
For cool days, about 5–12°C · Smart casual · 3 pieces from £110*
For cool days, about 5–12°C · Everyday · 4 pieces from £95*
For cool days, about 5–12°C · Smart casual · 3 pieces from £98*
For cool days, about 5–12°C · Everyday · 4 pieces from £125*
For cold days, about −5 to 5°C · Smart casual · 4 pieces from £85*
For mild days, about 12–20°C · Everyday · 2 pieces from £30*
Counted from 36 of these looks.
Black, grey, green and cream come up most often across these looks, so they make an easy base to build on.
Most whole outfits here cost between £183 and £317; the typical one is £196. Swap any piece to change the total.
Most pieces come from Barbour, Hunter, Albaray, Rains and The Couture Club. Each look checks out on the stores' own sites, one store at a time.