The only shoes a guy will ever need

To earn a place in your repertoire, a pair of shoes needs to go the extra mile, not just durable but also versatile. Shoes are one of the most expensive items in a man's wardrobe so we've selected a minimal set of shoes that together work for any occasion in any weather. And we do mean any. We aren't just talking about a day at the office and a workout at the gym. With these shoes you can go from the beach to the arctic to the bar to the rain forest to the office ... and to your own wedding.

  1. Start with British tan Chelsea boots for any season and nearly any occasion
  2. For athletic pursuits, add trail running shoes
  3. For the office, add oxblood brogue oxfords
  4. For summer and shorts, add boat shoes
  5. For braving the elements, add wellington boots
  6. For opera opening night and presentations to the board, add black balmorals
  7. For surviving the snowpocalypse, add Canadian insulated boots

We recommend shoes that last. Some, especially like Allen Edmonds, seem expensive up-front. A pair might cost $300. Have them recrafted twice every decade for $125. Recrafting is like getting a new shoe - new outsoles, new heels, new welting, new laces, new cork inlay, and refinished and polished uppers. Over ten years all this will set you back $550. Compare to buying a new pair of crappy shoes for $150 every two years, which comes to $750. Don't forget the hassle of all that extra shopping and breaking in a new pair of shoes.

Allen Edmonds Liverpool in Walnut

Allen Edmonds Liverpool in Walnut

1. British tan Chelsea boots

Smart savvy: Allen Edmonds Liverpool in walnut – List $445, often available at $245-$299

Chelsea boots, popularized by the Beatles during the British invasion in the 1960s, may be one of the most versatile shoes you can find. They look great with practically anything, from jeans to suits, as long as the trousers are trim and not flopping and pooling all over your feet. The British tan color works with anything but charcoal or black.

The Allen Edmonds Liverpool is handmade in Port Washington, Wisconsin and while its list price is steep, frequent sales get the price down to the mid $200s. For the ultimate deal, pick up a factory second, but not until it goes on sale. Factory seconds have minor and often unnoticeable blemishes that make them less than perfect. They normally go for $299; on sale they’ll be $245.

2. Trail running shoes

Smart savvy: Fila men's trail shoe, $20 at Costco

Athletic shoes wear out frequently and runners are supposed to replace them every so many miles. Trail shoes have the advantage of being a bit more stable and they typically come in rugged colors.

Costco sells a rotating selection of athletic shoes and the price usually can't be beat.


3. Oxblood brogue oxfords

Smart savvy: Allen Edmonds McAllister, $395, often available at $245-$299

While black balmorals are the most formal shoe you need to own, brogue oxfords in a burgundy or oxblood color are the most versatile. The color and style make them go with anything in your professional wardrobe. Charcoal suit. Navy suit. Gray suit. Chinos. Hell, even jeans. While the perforated brogue styling was invented originally for helping shoes drain from traipsing around soggy bogs in Scotland, today they add timeless interest and panache to a shoe, while spanning the lines from casual to formal. Note the oxford styling, like balmorals, make them spiffy enough to work with a suit, unlike the bluchers or derbies that just aren’t serve enough purposes to make it into the optimal minimal wardrobe.

The Allen Edmonds McAllister, is finely crafted and a great selection.

Sperry Topsiders - the white sole is traditional

Sperry Topsiders - the white sole is traditional

4. Boat shoes

Smart savvy: Sperry topsiders, $95

Like many of the best items for a man’s wardrobe, boat shoes have their roots in practicality. Boat decks are slippery, and the soles of boat shoes, fashioned after a dog’s paws, grip those slick surfaces so you don’t end up in the drink.

Sperry invented the first boat shoe, making all other brands imitations. And if you really must own only one casual summertime shoe, not even a pair of sandals – because you’re that minimal and resistant to clutter – boat shoes are it. They’re the only lace up shoe you can get away with sock-free with shorts. You could wear them bodysurfing and they’d only gain character. They go from beach to tiki torch dinner date.

Hunter Argyll boot

Hunter Argyll boot

5. Wellington boots

Smart savvy: Hunter Argyll – £120, often available at £50-75
Generally speaking it’s a good thing to be ordering footwear from England. Unlike the unisex mass market classic Hunter wellie that women have annexed for their exclusive use in the United States, Hunter’s harder to find models, only available across the pond and with roots in farming and hunting, are the killer app for guys for any need from mowing the lawn to wading across streams to commuting in town during a deluge. Hell, for areas whose winters aren’t too frigid (e.g., not Chicago or New York or Denver or Minneapolis), with a wellie liner or thick socks they’re also a perfect snow boot when there’s slush and salt and three inches of standing water at backed up street curbs.
Hunter invented Wellingtons in 1856 for getting around Scotland. These rugged models are completely waterproof, enabling treading through water at least a foot deep, and their calendared sole patterns provide great traction no matter what’s under foot. Cleaning them is as simple as hosing them down. I just replaced my pair of Hunter Argyll after nine years with an identical pair. Not bearing the Hunter branding, I like the Argylls because they promote inscrutable mystique.
The Balmoral is also a solid choice, in a muted green style evocative of military gear.
But for the price point, Argyll remains the best value. It used to be available in the US but now tends to only be found at UK outdoor retailer websites. The advantage of ordering from the UK is retailers tend to have a different policy toward who pays return shipping and you will often find they’ll pick up the cost. Nonetheless you’ll be paying in pounds sterling so keep an eye on the exchange rate and use a credit card with no foreign exchange fees.

6. Black balmorals

Smart savvy: Allen Edmonds Park Avenue
The formality of balmorals comes in their simplicity. Unlike bluchers or derbies that are relegated to the more casual side due to the extra flaps for laces, balmorals are dress shoes with everything nonessential stripped away, except possibly for a cap toe. They’re the perfect job interview shoe and don’t look out of place with a tuxedo. This is the dressiest shoe you need to own (because patent leather shoes worn once a year with a tux are so not worth it).

Allen Edmonds offers several balmorals, the optimal choice being the Park Avenue, owing to its timeless, conservative styling that’ll look on point regardless of what decade the latest fashion trend has latched onto. The company also offers a top-end version called Hopkinson, part of its Independence line, built on a different last and embracing your hard working feet in glove soft calfskin uppers and lambskin lining. Still at 25% more than the Park Avenue, all that luxury seems a bit superfluous. 

Kamik boots - made by Canadians in Canada

Kamik boots - made by Canadians in Canada

7. Canadian insulated boots

Covered in our Surviving the Deep Freeze post.