$100.00
A staple in your wardrobe that is reliable and simplistic. Enter the Cornwall a chelsea boot that solves...
Big Fans Big Deals
Disclosure: Big Fans Big Deals contains affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you.
$100.00
A staple in your wardrobe that is reliable and simplistic. Enter the Cornwall a chelsea boot that solves...
$149.95
Conquer wet winter streets in our style-savvy Emeree.This modern Chelsea boot gets a boost of height from a...
$250.00
The next time you're running out the door to walk your pup, slip on your Barbour Men's Flyweight Chelsea...
$88.00
The Birkenstock Bend Chelsea Suede Boot shows off a flash of everyday style, elevating our look with a...
$229.95
Warm and waterproof, the Blundstone Thermal Chelsea Boot come to our daily rotation with handsome style and...
$199.95
The Blundstone Classics Series Chelsea Boot has developed a reputation as a durable, stylish boot that can...
$189.95
The Original Series Chelsea Boot is the boot that started Blundstone's legacy of incredible comfort and...
$149.99
Built with a moisture-wicking lining and waterproof rubber, the Arcata Urban Chelsea Boot delivers everyday...
$99.99
There is something about the Bogs Kicker Rain Chelsea Neo Boot. These waterproof boots thrive in chilly and...
$94.99
When the rain starts to pour, we reach for the Amanda Plush II Chelsea Boot. Not only does it keep us warm...
$84.99
The Bogs Kicker Rain Chelsea II Boot gives us the confidence needed to face another storm, regardless of...
$79.99
Rainy summer day? Cue the Kicker Rain Chelsea Boot. These waterproof foot huggers keep our toes dry without...
$58.49
The waterproof BOGS Kicker Rain Chelsea II Boots keep our toes dry without hampering our look. The popular...
$42.50
When it seems like the sky will never stop dumping buckets of rain, we slip on the Bogs Sweetpea II Chelsea...
$159.95
The Chaco Fields Chelsea Waterproof Boot fits well on city walks and mountain strolls. The leather style is...
$159.95
The Fields Chelsea Boot from Chaco takes us from city life to mountain towns with heritage styling, premium...
$139.95
When it comes to hiking or walking from our car and into the grocery store, we're grateful to be wearing...
$229.95
Whether we're dressing up for date night or spending a few hours over our workbench, the Bull Run Chelsea...
$159.95
Rugged yet sophisticated, Forsake's Sofia Chelsea Boot is a stylish slip-on made with full-grain leather...
$145.00
Like your dads favorite boots but elevated, the Forsake Phil Chelsea Boot brings a timeless style and...
$135.00
When we're running around town with friends, the Lucie Chelsea Boot keeps us looking sharp while offering a...
$179.95
When temperatures drop and multiple layers become part of our everyday get-up, we pull on our Revel IV...
$87.48
If we scaled our favorite puffy jacket down to a shoe we'd have the KEEN Greta Chelsea Waterproof Boot. The...
$157.48
Warm and waterproof, the Marmot Chelsea Short Coat showcases a weather resistant shell and high-quality,...
$151.98
The Marmot Chelsea Coat provides us with an unbeatable combination of high-loft warmth, ample coverage, and...
$299.99
The Classic Chelsea Boot fits seamlessly into our winter wardrobe. We throw them on whether we're grabbing...
$298.95
Red Wing made their name with indestructible and comfortable work boots. For us, the Classic Chelsea Boot...
$101.97
Long days and gray skies don't have us choosing between comfort and style with the SOREL Slabtown 62...
$95.97
When dark clouds start to spit, the SOREL Emelie III WP Chelsea says, "bring it on." Sleek impermeable...
$76.97
Whether it's off-grid photo shoots or adventures around town, the SOREL Explorer STRT Chelsea Boot is a...
$71.98
The Brex Chelsea Boot from Sorel amps up the volume on style and functionality. It's built to live up to...
$69.98
The Hi-Line Chelsea Boot keeps us strutting in top-notch style without forgetting our comfort along the...
$32.45
What's more versatile then a good fleece pullover like the Stoic Chelsea Fleece Pullover? Not much. This...
$59.98
From wet-weather hunting trips to days on the boat, we're pulling on the XTRATUF Bristol Bay Chelsea Boot...
$109.99
100% Waterproof; Fully lined with Muckskin neoprene for flexibility; Lightweight midsole for comfort...
$170.00
Step into style and comfort with the Women's Taos Daily Chelsea Boots, meticulously designed for the modern...
$180.00
Classic clog comfort gets a support upgrade in this Chelsea boot built with the rocker bottom of the...