Uploaded August 2025 | Updated September 2026, 1 week ago
* Thanks for your time, @randallwestmore ! Follow his IG: instagram.com/randallwestmore
* We wear the Brandy and Black Matte Captains here: thursdayboots.com/products/mens-captain-lace-up-boot-black-matte
* Black vs Brown Boots: The Great Debate: youtube.com/watch?v=uqrHBs36SGw
Thursday Boot Company is probably the most popular boot brand in the United States, and one reason they got so popular is that their flagship Captain boot presented a relatively fresh take on Goodyear welted boots: it's slimmer and more versatile than traditional casual boots, that many were accustomed to, so it unlocked a new way of wearing boots for a lot of dudes. Especially since they're under $200.
Menswear continues to evolve ten-plus years after their debut, so the question I get asked a lot is more relevant than ever: how do you style Thursday boots? To find as many outfits as possible, I figured I'd head to Thursday's office in Manhattan and asked the guy who does all the styling for their product shots.
00:00 How to style Thursday Captain boots
00:55 Thursday's Rugged & Resilient vs Classic Leathers
01:38 Thursday boots with black leather jacket
02:46 Thursday boots with heritage menswear
03:10 Thursday boots with suit
03:35 Thursday boots business casual
04:48 Best pants for Thursday boots
05:30 Do Thursday boots need tapered pants or slim jeans?
07:05 Should you cuff jeans with Thursday boots?
07:49 How to wear brown boots and black pants
08:42 Should your belt match your boots?
09:43 How to wear Thursday boots in summer
10:21 Black vs brown boots
11:04 The best Thursday boots leather?
* Thanks for your time, @randallwestmore ! Follow his IG: instagram.com/randallwestmore
* We wear the Brandy and Black Matte Captains here: thursdayboots.com/products/mens-captain-lace-up-boot-black-matte
* Black vs Brown Boots: The Great Debate: youtube.com/watch?v=uqrHBs36SGw
Thursday Boot Company is probably the most popular boot brand in the United States, and one reason they got so popular is that their flagship Captain boot presented a relatively fresh take on Goodyear welted boots: it's slimmer and more versatile than traditional casual boots, that many were accustomed to, so it unlocked a new way of wearing boots for a lot of dudes. Especially since they're under $200.
Menswear continues to evolve ten-plus years after their debut, so the question I get asked a lot is more relevant than ever: how do you style Thursday boots? To find as many outfits as possible, I figured I'd head to Thursday's office in Manhattan and asked the guy who does all the styling for their product shots.
00:00 How to style Thursday Captain boots
00:55 Thursday's Rugged & Resilient vs Classic Leathers
01:38 Thursday boots with black leather jacket
02:46 Thursday boots with heritage menswear
03:10 Thursday boots with suit
03:35 Thursday boots business casual
04:48 Best pants for Thursday boots
05:30 Do Thursday boots need tapered pants or slim jeans?
07:05 Should you cuff jeans with Thursday boots?
07:49 How to wear brown boots and black pants
08:42 Should your belt match your boots?
09:43 How to wear Thursday boots in summer
10:21 Black vs brown boots
11:04 The best Thursday boots leather?
