Olive Shirt & Indigo Pants
$1,389Smart casual · 4 pieces · One checkout
Men's outfits with Chelsea boots
Chelsea boot outfits with slim jeans, trousers and knits, smart enough for the office. 23 complete looks from in-stock pieces, each one shoppable in a click per store.
23 looks
Bronze Jacket & Olive Shirt
$1,792Smart casual · 4 pieces · One checkout
Olive Jacket & Bitter Gold Knit
$1,762Smart casual · 4 pieces · One checkout
Charcoal Heather Jacket & Pink Knit
$1,500Smart casual · 5 pieces · One checkout
Blue Jacket & Black Knit
$893Smart casual · 5 pieces · One checkout
Sage Jacket & Espresso Bean Knit
$1,324Everyday · 4 pieces · One checkout
Jet Black Jacket & Smoked Rose Polo
$573Everyday · 5 pieces · One checkout
Navy Jacket & Olive Shirt
$1,644Smart casual · 4 pieces · One checkout
Gray Jacket & Moss Knit
$481Smart casual · 4 pieces · 3 stores
Black Jacket & Smoked Rose Polo
$545Smart casual · 4 pieces · One checkout
Green Fern Knit & Dark Brown Trousers
$1,229Smart casual · 4 pieces · One checkout
Green Fern Knit & Charcoal Trousers
$1,024Smart casual · 3 pieces · One checkout
How to wear Chelsea boots
Counted from the 23 looks above, all built from pieces in stock today.
What goes with Chelsea boots
- On top
- Knitwear or sweatshirts & hoodies
- Bottoms
- Pants or trousers
- Layers
- Jackets
Colors that work
Brown, green, black and grey come up most often across these looks, so they make an easy base to build on.
What a complete look costs
Most whole outfits here cost between $694 and $1,389; the typical one is $994. 7 include a piece on sale. Swap any piece to change the total.
Brands in these looks
Most pieces come from Todd Snyder, Represent, Faherty, Miansai and Barbour. Each look checks out on the brands' own sites, one store at a time.