Uploaded June 2025 | Updated September 2026, 1 week ago

---

* Check out the Legend: stridewise.com/thursday-boot-co-legend-chelsea-boot
* Full article + pics: stridewise.com/thursday-legend-review
* My top 10 Chelsea boots: stridewise.com/best-chelsea-boots

Chelsea boots are usually smart casual or business casual, which is why it took Thursday Boot Company a few years of selling those sorts of Chelseas before coming out with the more rugged and outdoorsy Legend — and it promptly outsold their more traditional Chelseas. Here I'll break down how the Legend is different in the market by comparing it to NINE other Chelseas: four from Thursday and five from other brands.

00:00 Why I'm reviewing Thursday's Legend
00:49 Chelsea boots vs work boots
02:09 Thursday Legend boots leathers
03:17 How Thursday's Legend is made
04:05 Thursday Legend vs Cavalier vs Duke vs Journeyman vs General Purpose
05:40 Are Thursday Legends worth it?
07:48 Thursday Legend sizing
08:58 Thursday Legend pros
10:05 Thursday Legend cons
11:30 Goodbye!