Uploaded March 2025 | Updated September 2026, 1 week ago
↓Links to these boots below ↓
* My 13 Favorite Chelseas of All Time: stridewise.com/best-chelsea-boots
* That 15-Item Fashionproof Capsule Wardrobe: youtube.com/watch?v=w2D3IXjMCYE
* Full article + pics: stridewise.com/best-boots-for-travel
1. Luca, the hybrid sneaker boot: stridewise.com/luca-chelsea-sneaker-boot
2. Thursday's Cavalier, the versatile Chelsea: stridewise.com/thursday-boots-cavalier-chelsea
3. Red Wing's Weekender, the almost-work boot: stridewise.com/red-wing-weekender-chelsea or it's also here avantlink.com/click.php?tt=cl&merchant_id=d540ae58-3127-456a-a787-b8339c28f9f0&website_id=e89f9a2e-0bc4-482a-bd5a-2c1205df0dcd&url=https%3A%2F%2Fwww.redwingshoes.com%2Fheritage%2Fmens%2FWeekender-Chelsea-03311.html
4. Ariat's Wexford, the waterproof but stylish: amzn.to/3CxKzvr
5. Beckett Simonon's Easton, the sleek side zip: stridewise.com/easton-side-zip-boot
6. Allen Edmonds Tompkins, the wooly winter boot: stridewise.com/allen-edmonds-tompkins
If you're looking for something to travel in, many of your usual criteria for picking a boot go out the window: you tend to want something lighter, more versatile, and easier to pack or take through metal detectors. Whether you're looking for something to wear in a snowy wonderland or something that can keep your feet dry when trudging through puddles, there's something for everyone on this list. If you hate laces.
00:00 What makes a good travel boot?
02:49 Sneaker Boot: Luca's Terra Sneaker
04:36 Versatile: Thursday's Cavalier
05:51 Casual: Red Wing's Weekender
06:56 Waterproof: Ariat's Wexford
08:09 Side Zip: Beckett Simonon's Easton
09:02 Winter Travel Boot: Allen Edmonds' Hamilton
↓Links to these boots below ↓
* My 13 Favorite Chelseas of All Time: stridewise.com/best-chelsea-boots
* That 15-Item Fashionproof Capsule Wardrobe: youtube.com/watch?v=w2D3IXjMCYE
* Full article + pics: stridewise.com/best-boots-for-travel
1. Luca, the hybrid sneaker boot: stridewise.com/luca-chelsea-sneaker-boot
2. Thursday's Cavalier, the versatile Chelsea: stridewise.com/thursday-boots-cavalier-chelsea
3. Red Wing's Weekender, the almost-work boot: stridewise.com/red-wing-weekender-chelsea or it's also here avantlink.com/click.php?tt=cl&merchant_id=d540ae58-3127-456a-a787-b8339c28f9f0&website_id=e89f9a2e-0bc4-482a-bd5a-2c1205df0dcd&url=https%3A%2F%2Fwww.redwingshoes.com%2Fheritage%2Fmens%2FWeekender-Chelsea-03311.html
4. Ariat's Wexford, the waterproof but stylish: amzn.to/3CxKzvr
5. Beckett Simonon's Easton, the sleek side zip: stridewise.com/easton-side-zip-boot
6. Allen Edmonds Tompkins, the wooly winter boot: stridewise.com/allen-edmonds-tompkins
If you're looking for something to travel in, many of your usual criteria for picking a boot go out the window: you tend to want something lighter, more versatile, and easier to pack or take through metal detectors. Whether you're looking for something to wear in a snowy wonderland or something that can keep your feet dry when trudging through puddles, there's something for everyone on this list. If you hate laces.
00:00 What makes a good travel boot?
02:49 Sneaker Boot: Luca's Terra Sneaker
04:36 Versatile: Thursday's Cavalier
05:51 Casual: Red Wing's Weekender
06:56 Waterproof: Ariat's Wexford
08:09 Side Zip: Beckett Simonon's Easton
09:02 Winter Travel Boot: Allen Edmonds' Hamilton
