Leather Footwear

Versatile footwear can be hard to come by. Most shoes have individual utility: sneakers for running or walking, brogues for looking good in your best gray wool suit, and duck boots for foul weather. It can be comforting to know the right circumstances for each pair of shoes, but graduating into versatility will take you to a whole new level.

A good pair of leather shoes or boots can be that do-it-all shoe for you. If you take care of them (cf. shoe trees, shoe brush, conditioner), they’ll pay dividends for years and years.

1. Original Chippewa Plain Toe Oxford

Chippewa’s oxford has an appealing silhouette and low profile, and the plain toe and chunky Vibram sole offer a nice contrast between workwear and more casual detailing. From their new Originals series, these oxfords hold up like a work boot but are lighter and sleeker, so they’ll be something you turn to every day. And the Goodyear welted construction means you can throw a new sole on these whenever the old sole wears out.

@ Snake Oil Provisions ($229)

2. Haco Schuh

Made in Bavaria, these Haco Schuh shoes stand out for all the right reasons. They look so little like anything else out there, thanks to the Bellows tongue and side lacing. The rugged sole and olive suede will keep these shoes on your feet and you looking good.

@ Inventory ($295)

3. Alden Cooper Longwing

I chose to list these Aldens because they’re a rare blend of style and substance – the longwing style looks great dressed up or down, and the commando sole is not dainty in the least, so these can be great walkers as well. The depth of color in the walnut calf leather is gorgeous. These are have-the-rest-of-your-life shoes.

@ Unionmade ($535)

4. Red Wing Beckman Chukka 9017

When people think of Red Wing, they often think of the iconic moccasin toe boots that have been workwear staples for a long time (and for good reason). However, this Beckman chukka is just as hard wearing as anything else Red Wing produces but has a more refined look that ensures you’ll get compliments if you’re wearing these with slacks or jeans. Just like all the other shoes featured today, the welt ensures that you can resole these anytime and breathe new life into them for years and years.

@ Unionmade ($340)

5. Thorogood x Steven Alan Leather Boot

Thorogood makes strong boots and shoes in the USA, and this collaboration with Steven Alan has traded out down some of the workwear influences in Thorogood’s styling for a smoother profile and all-around, versatile look. The six-inch ankle height is tall enough to keep you comfortable in winter but short enough to not suffocate your feet on long walks. The speed hooks ensure quick lacing and the Goodyear welt is a great touch.

@ Steven Alan ($138, on sale from $198)

Fun Fact: Our splash image today is from the National Archives, the drawing for Patent #5255452, "Method and Means for Creating Anti-Gravity Illusion," credited to Michael Jackson, 06/29/1992 - 11/23/2005.