Black shirt, green pants & brown Timberland boots
$488For cool days, about 40–55°F · Smart casual · 3 pieces from $119
What to wear with Timberland boots
Timberland boot outfits: the 6-inch boot with pants, cords or jeans and a knit or a hoodie, or with a dress. 41 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026
What goes with Timberland boots
- On top
- Knitwear or shirts
- Bottoms
- Pants or skirts
- Layers
- Jackets or puffers & parkas
With brown · 30 looks
Vest, blue hoodie & brown pants
$637For cool days, about 40–55°F · Everyday · 4 pieces from $99
Black puffer jacket, camo hoodie & black pants
$870For cold days, about 25–40°F · Outdoors · 5 pieces from $120
Navy polo, brown pants & brown Timberland boots
$515For mild days, about 55–70°F · Smart casual · 4 pieces from $25
Black Nuptse jacket, white shirt & green pants
$1,060For mild days, about 55–70°F · Everyday · 4 pieces from $190
Fleece, black sweater & grey pants
$1,165For cool days, about 40–55°F · Everyday · 4 pieces from $250
With black · 22 looks
With cream · 16 looks
With green · 14 looks
All looks
41 looks
Black dress & green Timberland boots
$435For mild days, about 55–70°F · Smart casual · 2 pieces from $180
Would you wear it?
Green jacket, grey tee & jeans
$776For cool days, about 40–55°F · Outdoors · 5 pieces from $65
Would you wear it?
Cream sweater, beige midi skirt & black Timberland boots
$441For cool days, about 40–55°F · Smart casual · 4 pieces from $58
Would you wear it?
Corduroy jacket, charcoal turtleneck & black pants
$925For cool days, about 40–55°F · Smart casual · 4 pieces from $220
Would you wear it?
Blue puffer jacket, black sweater dress & brown Timberland boots
$566For cold days, about 25–40°F · Outdoors · 3 pieces from $148
Grey polo, green pleated pants & brown Timberland boots
$721For mild days, about 55–70°F · Everyday · 4 pieces from $198
Grey cardigan, charcoal dress & green Timberland boots
$664For cool days, about 40–55°F · Smart casual · 3 pieces from $169
Black jacket, burgundy tee & brown pants
$626For mild days, about 55–70°F · Everyday · 5 pieces from $65
Brown overshirt, olive fleece & brown pants
$583For cool days, about 40–55°F · Outdoors · 4 pieces from $89
Grey sweater, olive pants & beige Timberland boots
$480For cool days, about 40–55°F · Everyday · 4 pieces from $80
Tan sweater, blue pants & brown Timberland boots
$486For cool days, about 40–55°F · Smart casual · 3 pieces from $88
Navy dress, pink Timberland boots & pink bag
$415For warm days, about 70–85°F · Smart casual · 3 pieces from $180
How to wear Timberland boots
Counted from 33 of these looks.
What goes with Timberland boots
- On top
- Knitwear or shirts
- Bottoms
- Pants or skirts
- Layers
- Jackets or puffers & parkas
Colors that work
Brown, black, cream and green 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 $583 and $1,665; the typical one is $1,060. 5 include a piece on sale. Swap any piece to change the total.
Brands in these looks
Most pieces come from Timberland, Kith, What Goes Around Comes Around, The North Face and Made Some. Each look checks out on the stores' own sites, one store at a time.