Oak Street Bootmakers

Chicago-made boots and shoes since 2010

American manufacturer specializing in casual boots, camp mocs, and boat shoes crafted with premium leather.

76 items available

at 2 stores

Sizing Guide
Based on community feedback, generally runs true to size though some customers size down 0.5 from sneakers. Individual fit varies by model - contact Oak Street for guidance.
Construction & Materials
Goodyear welt construction with premium leather. Blake stitch construction used on dress shoes and boat shoes.
Heritage & History
Founded in 2010 in Chicago with focus on American-made casual footwear.
Care Instructions
Regular conditioning with quality leather conditioners recommended. Cedar shoe trees recommended for shape retention. Professional resoling available.
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Oak Street Bootmakers

Bresciani Officer Socks - Field Merino Wool Blend

$ 126

Oak Street Bootmakers

Bresciani Officer Socks - Heraldry Merino Wool Blend

$ 126

Oak Street Bootmakers

Shearling House Moc - Single Malt Deadstock Desert Suede

$ 198

Oak Street Bootmakers

Boat Shoe - Brown Chromexcel

$ 209

Oak Street Bootmakers

Boat Shoe - Natural Chromexcel

$ 209

Oak Street Bootmakers

Boat Shoe - Navy Chromexcel

$ 209

Oak Street Bootmakers

Slip Moc - Natural 12oz Chromexcel

$ 229

Oak Street Bootmakers

Slip Moc - Brown 12oz Chromexcel

$ 229

Oak Street Bootmakers

Bit Moc - Natural Chromexcel

$ 262

Oak Street Bootmakers

Camp Moc - Brown Chromexcel

$ 262

Oak Street Bootmakers

Camp Moc - Natural Chromexcel

$ 262

Oak Street Bootmakers

Camp Moc - Natural Chromexcel Roughout

$ 262

Oak Street Bootmakers

Camp Moc - Navy Chromexcel

$ 262

Oak Street Bootmakers

Bit Moc - Brown Chromexcel

$ 262

Oak Street Bootmakers

Trail Oxford - Brown Chromexcel

$ 269

Oak Street Bootmakers

Trail Oxford - Natural Chromexcel

$ 269

Oak Street Bootmakers

Trail Oxford - Navy Chromexcel

$ 269

Oak Street Bootmakers

Boat Shoe - Natural Chromexcel Roughout

$ 298

Oak Street Bootmakers

Penny Moc - Brown Chromexcel

$ 328

Oak Street Bootmakers

Trail Oxford - Navy Orion Suede

$ 328

Oak Street Bootmakers

Penny Moc - Natural Chromexcel

$ 328

Oak Street Bootmakers

Penny Moc - Black Latigo

$ 336

Oak Street Bootmakers

Bit Moc - Black Latigo

$ 336

Oak Street Bootmakers

Rowing Oxford - Natural Chromexcel Roughout

$ 348

Oak Street Bootmakers

Rowing Oxford - Navy Chromexcel

$ 348

Oak Street Bootmakers

Beefroll Penny Loafer - Brown Chromexcel

$ 348

Oak Street Bootmakers

Beefroll Penny Loafer - Natural Chromexcel

$ 348

Oak Street Bootmakers

Beefroll Penny Loafer - Navy Chromexcel

$ 348

Oak Street Bootmakers

Boat Shoe - Snuff Janus Suede

$ 348

Oak Street Bootmakers

Rowing Oxford - Natural Chromexcel

$ 348

Oak Street Bootmakers

Rowing Oxford - Brown Chromexcel

$ 348

Oak Street Bootmakers

Cap-Toe Lakeshore Boot - Brown Chromexcel

$ 363

Oak Street Bootmakers

Cap-Toe Lakeshore Boot - Natural Chromexcel

$ 363

Oak Street Bootmakers

Cap-Toe Lakeshore Boot - Color 8 Chromexcel

$ 363

Oak Street Bootmakers

Cap-Toe Lakeshore Boot - Black Chromexcel

$ 363

Oak Street Bootmakers

NATO Marine Scarves - Merino Wool Knit Bundle

$ 366

Oak Street Bootmakers

Lug Penny Moc - Black Scotch Grain Chromexcel

$ 368

Oak Street Bootmakers

Bit Loafer - Natural Chromexcel

$ 368

Oak Street Bootmakers

Lug Bit Moc - Brown Scotch Grain Chromexcel

$ 368

Oak Street Bootmakers

Lug Penny Moc - Brown Scotch Grain Chromexcel

$ 368

Oak Street Bootmakers

Lug Bit Moc - Black Scotch Grain Chromexcel

$ 368

Oak Street Bootmakers

Bit Loafer - Brown Chromexcel

$ 368

Oak Street Bootmakers

Trench Boot - Natural Chromexcel Roughout

$ 390

Oak Street Bootmakers

Trench Boot - Brown Chromexcel

$ 390

Oak Street Bootmakers

Trench Boot - Color 8 Chromexcel

$ 390

Oak Street Bootmakers

Trench Boot - Black Chromexcel

$ 390

Oak Street Bootmakers

Trench Boot - Natural Chromexcel

$ 390

Oak Street Bootmakers

Camp Boot - Black Chromexcel

$ 448

Oak Street Bootmakers

Camp Boot - Brown Chromexcel

$ 448

Oak Street Bootmakers

Camp Boot - Natural Chromexcel

$ 448

Oak Street Bootmakers

Camp Boot - Natural Chromexcel Reverse

$ 448

Oak Street Bootmakers

Storm Boot - Natural Chromexcel Roughout

$ 454

Oak Street Bootmakers

Storm Boot - Black Chromexcel

$ 454

Oak Street Bootmakers

Storm Boot - Brown Chromexcel

$ 454

Oak Street Bootmakers

Storm Boot - Natural Chromexcel

$ 454

Oak Street Bootmakers

Trench Oxford - Black Chromexcel

$ 462

Oak Street Bootmakers

Trench Oxford - Natural Chromexcel

$ 462

Oak Street Bootmakers

Shearling Camp Boot - Brown Chromexcel

$ 468

Oak Street Bootmakers

Shearling Camp Boot - Natural Chromexcel

$ 468

Butterscotch • Oak Street Bootmakers

Oak Street x Butter Scotch - 93 Trench Oxford

$ 475

Oak Street Bootmakers

Trench Oxford - Aged Bark Chieftain Roughout

$ 478

Oak Street Bootmakers

Field Boot - Aged Bark Chieftain Roughout

$ 488

Oak Street Bootmakers

Trench Chukka - Aged Bark Chieftain Roughout

$ 488

Oak Street Bootmakers

Cap-Toe Trench Boot - Black Chromexcel

$ 498

Oak Street Bootmakers

Cap-Toe Trench Boot - Brown Chromexcel

$ 498

Oak Street Bootmakers

Cap-Toe Trench Boot - Natural Chromexcel

$ 498

Oak Street Bootmakers

Field Boot - Natural Chromexcel Roughout

$ 518

Oak Street Bootmakers

Field Boot - Natural Chromexcel

$ 518

Oak Street Bootmakers

Field Boot - Black Chromexcel

$ 518

Oak Street Bootmakers

Trench Chukka - Coach Waxy Mohawk

$ 524

Butterscotch • Oak Street Bootmakers

Oak Street Bootmakers x Butter Scotch - Deckard Boot

$ 525

Butterscotch • Oak Street Bootmakers

Oak Street Bootmakers x Butter Scotch - Double Black Deckard Boot

$ 525

Butterscotch • Oak Street Bootmakers

Oak Street x Butter Scotch - 93 Vibram Trench Boot

$ 550

Butterscotch • Oak Street Bootmakers

Oak Street x Butter Scotch - Lo Fi Trench Oxford

$ 550

Butterscotch • Oak Street Bootmakers

Oak Street x Butter Scotch - 93 Cap Toe Trench Boot

$ 555

Butterscotch • Oak Street Bootmakers

Oak Street Bootmakers x Butter Scotch - Black Oil Tan Roughout Trench Boots

$ 575