I’ve written it before, I’ve done a podcast on it, and I’ll say it again: a smart wardrobe starts with good shoes. While there are some places where one could cut corners or “cheat” with less expensive shirts, ties, pants, and even suits, shoes are the one area where playing it cheap really doesn’t pay off in the long run.

And when I talk about shoes, I’m talking about real shoes from companies whose heritage, foundation and strength is shoes. This doesn’t include designer labels who grind out a new collection every season. If someone has the money to blow thousands annually on the new and fabulous, super. I’m not interested in that, and I don’t think most pragmatic and discerning men are, either. It’s about shoes that work now, will work next year and will continue to work for the rest of your life. Good shoes can be expensive, but they are worthy investments. This is about the long game. Take good care of them with regular conditioning and shining, heel and sole maintenance and cedar shoe trees between wearings, and they’ll last longer than a good car.

For the cooler months, I have a thing for chukka boots. They’re handsome, masculine, elegant and practical for just about any occasion, depending on the color and finish. Suede is obviously a more casual flavor, while polished leather in a dark shade with a matching (or closely matching) sole can also be worn in dressier suit and tie modes. I have a few pairs, and they’re my steady fall/winter go-to boots with suits or jeans.

There are other less expensive boots from brands like Cole Haan or Florsheim, but I cannot endorse the quality. The leather looks and feels cheap, and the construction is questionable. I’m much more interested in spending more and ultimately getting more over time. I’d rather have two great pairs of shoes for more money than six cheap pairs that won’t last more than two years.

Here is a curated selection of my absolute favorites. Some are a polished leather, which works for both dress or casual, and others are suede, which is casual.

Alden

Alden Shell Cordovan Chukka Boot in "Color 8" (burgundy)

Alden Shell Cordovan Chukka Boot in “Color 8” (burgundy)


The Chukka Boot in Shell Cordovan is a classic two-eyelet chukka. This Alden masterpiece is a standard-bearer in superlative boot making, made with a shell cordovan upper produced by one of the oldest tanneries, using a process that takes six months to produce a soft, supple and durable leather. It’s handcrafted and assumes the shape of your foot for a true custom fit. All Alden shoes are made in Massachusetts.

It’s available in “Color 8” (dark burgundy – shown) or black. $712.

www.theshoemart.com

Alden Unlined Flex Welt Suede Chukka in dark brown.

Alden Unlined Flex Welt Suede Chukka in dark brown.

The Unlined Flex Welt Suede Chukka is another Alden classic, built on their Leydon last. It features a soft suede calfskin upper, a vegetable-tanned insole and a flex construction outsole. It comes in black, hunting green, dark brown (shown), tan and snuff. $528.

www.theshoemart.com

Crockett & Jones

Crockett & Jones Brecon in dark brown country calf.

Crockett & Jones Brecon in dark brown country calf.


The Brecon boot from Crockett & Jones in England is made from the finest calf or country grain leather and Dainite rubber soles with a storm welt. It’s a classic and totally elegant shoe from one of the finest shoe makers in the world.

The Brecon comes in black or dark brown country calf (shown). $670.

crockettandjones.com

Allen Edmonds

Allen Edmonds Dundee 2.0 in black.

Allen Edmonds Dundee 2.0 in black.


The Dundee 2.0 is almost a dead ringer for Alden’s chukka, differing most notably with a three-eyelet design. (How many ways can one remix a chukka boot?) It’s a classic design made with a premium calfskin upper, a Double Butyl outsole and Poron insole, delivering superior durability and comfort. The Dundee is made in the U.S.A. with Goodyear welt construction and is eligible for Allen Edmonds’ re-crafting services.

The plain leather version comes in black (shown), brown or walnut burnished calf. The suede version comes in loden, snuff or “bitter chocolate.” There is also a brown grain leather version with a Dainite rubber sole. $395.

www.allenedmonds.com

Grenson

Grenson suede Marcus chukka boots in chocolate.

Grenson suede Marcus chukka boots in chocolate.


Grenson in England is one of my favorite shoe companies, with a rich heritage, superlative construction standards, and designs ranging from regular classics to modern twists on classics. Their suede Marcus chukka boot is timeless.

These beauties come in chocolate (shown), black, charcoal, almond and navy. $370.

www.grenson.com/us

Johnston & Murphy

Johnston & Murphy Copeland chukka boot in Red Brown Oiled Full Grain.

Johnston & Murphy Copeland chukka boot in Red Brown Oiled Full Grain.


The Johnston & Murphy chukka offerings are strictly casual. My favorite is their Copeland Chukka. It’s made with water-resistant leather or suede, sheepskin lining and a natural crepe rubber sole, which is extremely comfortable and durable.

I’m not a fan of light stitching that contrasts with a dark leather or suede, drawing unnecessary attention to the seams of a shoe, but the Copeland model comes in a couple of nice color configurations, particularly the Red Brown Oiled Full Grain (shown) and the Camel Suede. $155.

www.johnstonmurphy.com

Clarks

Clarks Original Desert Boot in dark brown suede.

Clarks Original Desert Boot in dark brown suede.


Also strictly casual, the original Clarks Desert Boot is a timeless classic. With a simple but durable construction and a crepe rubber sole, it’s a brilliant and extremely comfortable alternative to sneakers. It’s my go-to boot for walking the dogs.

The Clarks Desert Boot is available in a huge variety of colors in the original suede or finished leather. My favorites are dark brown suede and the oakwood tan suede. $130.

www.clarksusa.com