It’s a lot of work to explore different brands, silhouettes, aesthetics, and stores, narrowing down what you like most. I’m reminded of Greg from No Man Walks Alone replying to a compliment on his store’s well-curated selection of goods, saying that finding the gems at a show like Pitti is incredibly difficult, requiring lots of patience wading through a nearly unlimited number of booths. Sometimes it’s nice for someone—like Greg—to simply say, “here are the best options. Choose from these.”

In the same spirit, I thought I’d share the five pairs of shoes I think you would be best-served buying—either as a capsule shoe wardrobe or simply as your starting point as you build a larger wardrobe. It goes without saying this advice comes from a point of view that favors versatility with tailoring, denim and chinos as my “what I wore” posts will attest. As a complement to this advice, read my “Versatile shoe” piece from last year. Thankfully there are lots of brands who make each one, so I’ll recommend a maker for each type at different price points for you to consider. In no particular order:

1- Chukka Boots

I wear these most of the time October through April. My chukkas are snuff suede with a Dainite sole so that I never think twice about wearing them if it’s wet out. I hiked Quiraing at the Isle of Skye wearing them, so they’re rugged enough in a pinch. Versatility wise, suede is the best, and with a more pointed toe, you’ll be able to wear them with a sport coat just as easily as with a full workwear fit. A rounder toe would help them match more closely with denim or moleskin pants.

Low price: Meermin (same as mine). Mid: Kent Wang. Mid-High: Sid Mashburn.

 

2- Penny loafers

I wear these most of the time May through September. Mine are—surprise—snuff suede. I walked throughout the cobblestone plazas and streets of Florence, seeing David, visiting the Uffizi Gallery and enjoying Florentine steak in mine. I prefer an elongated toe on these to the rounder ones you might see on a classic Alden, but that’s a personal preference.

Low price: Meermin. Mid-high: Sid Mashburn.

 

3- Longwings or Wingtips

I’ve always loved the brogue, at time shifting my preferred model back and forth between the wingtip silhouette or the long wing silhouette. I’m currently in the long wing camp, but I only own wing tips. Perhaps the grass is always greener. Mine are a pebble grain with Dainite sole, which came with me this past winter during our travels in Scotland. The Dainite sole came in handy for the rugged outdoors. I wore them on our road trip through the highlands, from Glasgow to Glencoe and Fort William, during which we stopped many times to jump out and photograph the scenery. Versatility wise, they can indeed be worn with denim, but really only dark denim. They look great with flannel or tweed trousers.

Low price: Meermin. Mid: Brooks Brothers. Super High Grail: Polo Cordovan.

 

4- Cap-toe Oxfords

You need something to wear dressed up more than just a sportcoat and jeans. For many years I went through that phase where you hate black shoes, and even today I think probably most of us could get away with only dark brown calf cap-toes in this category. But I think around the time Skyfall came out I realized black shoes in a tapered, chiseled toe last can make you look like James Bond – or, more realistically, they can make you feel like you look like James Bond. In any case, dark brown will help you through almost all the time, and it looks great with navy suits, gray suits, the navy blazer with gray trousers look, and almost every other tailored outfit.

Low: Meermin. Mid: Kent Wang. High: Carmina.

 

5- The Wild card

I know I said up front I’d tell you exactly what to buy, but this last one is going to come down to you making a decision for yourself based on your personal taste. It’s the dressed-down-but-contemporary-and-stylish slot, and which one you pick will depend solely on your preferences. For me, it’s a canoe moccasin, which I wear constantly. I walked from the Colosseum, the Roman Forum, and all the way to the Spanish Steps in mine. For others, it might be a pair of sleek white sneakers: they look great with jeans, khakis and some brave souls even wear them with tailoring. Other options are Wallabees and desert boots. Instead of prescribing exactly what to get, take stock of your aesthetic preferences and make a choice to help fill out your own individual wardrobe.

My favorite canoe mocs: Oak Street. My favorite white sneaker: Tretorn. My favorite desert boot: J.Crew.

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