With tailored touches and quality craftsmanship, the Lustir chukka boot from Madden is an upgraded version of a classic. This pair features a i…+

Diversify your wardrobe as we move to chillier weather with the Rucci Chelsea boot from Florsheim. Classically crafted with a sleek silhouett…+

Sharpen up every day fits with the Balen boot from Tommy Hilfiger. The ankle boot features burnished details and a gentle branding that bring …+

Start your day by wearing the Vance Co. Pratt boot. The zipper along the side stretch gores updates this ankle boot.

Get the most out of chilly days when you pair the Willyt boot with your favorite layered look. The steel toe adds a secure highlight, while the sl…+

Upgrade any cool weather look with the Marshall boot from Vanco Co. This Chelsea boot features a classic design with a slim stacked wood heel a…+

You can't go wrong with the classic style of the Harken chukka boot from Steve Madden. This desert boot features a sleek 3-eye lace-up and co…+

Add some edge to your bomber jacket/black jean combo with the Tommy Hilfiger Nyo boot. Welt stitches and a sporty sole bring a contrasting to…+

The Morris boot from Clarks will become a new staple in your cool weather wardrobe. The waterproof construction and layered Extreme Comfort f…+

Bolster your chilly weather wardrobe with the Renegade Chelsea boot from Florsheim. This sharp boot sports a leather design and classic look tha…+

Take on the elements in the Redwood Falls chukka boot from Timberland. Boasting a seam-sealed construction, this lace-up boot is equipped wit…+

Show off classic style this cool weather season with the Ransom Chelsea boot from Dockers. This ankle boot features exposed stitching and a st…+

Exude an air of sophistication in the Langford boot from Vance Co. The cushioned collar and tongue lend exceptional comfort, while the rubbe…+

Opt for the Vance Co. Vaughn chukka boot that goes well with your off-duty style as well as party looks. Rendered in soft vegan synthetic, this boo…+

Add to your professional wardrobe with the Taft Chukka boot. Crafted from premium leather, this pair sports a classic look that pairs well with all m…+

Make a statement in any weather with the Lookout Waterproof boot from Florsheim. Crafted with a waterproof leather upper, this lace-up boot e…+

Make an elite entry with the Boston boot from Taft. The lace-up boot boasts a mixed-media upper comprising suede and full-grain leather that creat…+

Bolster your chilly weather wardrobe with the Renegade boot from Florsheim. This rugged boot sports a leather design and classic look th…+

Lace into the Salter boot from Harley-Davidson for a versatile addition to your wardrobe. This pair features a soft leather lining and full grain leat…+

Dress to impress in the Orson chukka boot from Vance Co. The textured pattern on the sole and contrast overlay at the collar add to the interest…+