Uploaded March 2026 | Updated September 2026, 1 week ago
- I turn invasive hogs into cool leather products that help farmers: badleathergoods.com
- Give a follow to @AlejandroJomar!
- Our review of Tecovas youtube.com/watch?v=KFxlAOD1k4E
- How anyone can wear WESTERN shirts: youtube.com/watch?v=o6APwe2tR_A
- The complete guide to DENIM shirts: youtube.com/watch?v=Z2ctuNsRvts
- The weirdest exotic leathers from a cowboy boot collector youtube.com/watch?v=oatZOdZVg3s
Boots we mention:
- Alejandro's cowboy boots from Thursday: stridewise.com/thursday-cowboy-boots-desperado
- Tecovas bestselling Roper boot stridewise.com/mens-roper-boots-the-earl-tecovas
- Tecovas' dressy lizardskin boot tecovas.sjv.io/nLPN5X
- Chisos, the advanced choice: stridewise.com/chisos-no-2-square-toe-cowboy-boot
Cowboy boots are one of the few boots that I haven't spent a lot of time talking about but they're surprisingly versatile if you can avoid looking ostentatious.
So I brought in Alejandro Jomar, a New York–based tailor and menswear YouTuber who’s been wearing cowboy boots for years. We break down different outfits ranging from casual or dressy, what jeans actually work with them, and simple outfits that make them feel normal — even if you don’t live anywhere near a ranch.
00:00 Square Toe vs Round Toe Cowboy Boots
01:11 Which Cowboy Boot Leathers Dress Up Best?
02:44 How to wear cowboy boots with jeans
03:45 Do you cuff your jeans with cowboy boots?
04:32 a denim Western outfit
05:58 how to wear a tshirt with cowboy boots
07:05 chinos with western boots
07:32 best jackets for cowboy boots
08:11 sport jacket and cowboy boots
09:19 can you wear cowboy boots with a suit?
09:57 wrapping up
- I turn invasive hogs into cool leather products that help farmers: badleathergoods.com
- Give a follow to @AlejandroJomar!
- Our review of Tecovas youtube.com/watch?v=KFxlAOD1k4E
- How anyone can wear WESTERN shirts: youtube.com/watch?v=o6APwe2tR_A
- The complete guide to DENIM shirts: youtube.com/watch?v=Z2ctuNsRvts
- The weirdest exotic leathers from a cowboy boot collector youtube.com/watch?v=oatZOdZVg3s
Boots we mention:
- Alejandro's cowboy boots from Thursday: stridewise.com/thursday-cowboy-boots-desperado
- Tecovas bestselling Roper boot stridewise.com/mens-roper-boots-the-earl-tecovas
- Tecovas' dressy lizardskin boot tecovas.sjv.io/nLPN5X
- Chisos, the advanced choice: stridewise.com/chisos-no-2-square-toe-cowboy-boot
Cowboy boots are one of the few boots that I haven't spent a lot of time talking about but they're surprisingly versatile if you can avoid looking ostentatious.
So I brought in Alejandro Jomar, a New York–based tailor and menswear YouTuber who’s been wearing cowboy boots for years. We break down different outfits ranging from casual or dressy, what jeans actually work with them, and simple outfits that make them feel normal — even if you don’t live anywhere near a ranch.
00:00 Square Toe vs Round Toe Cowboy Boots
01:11 Which Cowboy Boot Leathers Dress Up Best?
02:44 How to wear cowboy boots with jeans
03:45 Do you cuff your jeans with cowboy boots?
04:32 a denim Western outfit
05:58 how to wear a tshirt with cowboy boots
07:05 chinos with western boots
07:32 best jackets for cowboy boots
08:11 sport jacket and cowboy boots
09:19 can you wear cowboy boots with a suit?
09:57 wrapping up
