5 Pairs of Shoes You Should Buy for a Classic Casual Wardrobe

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.


Community Design: The Massdrop Chukka

If you spend time on Styleforum, you understand what it’s like to be part of an enthusiast community. You know the archetypes – from noob to tastemaker – and the abbreviations, from BB, ESF, and OCBD, to C&J and GMTO. You’ve also probably seen users band together to get the products they wanted – this is a core piece of any enthusiast community, and it’s why we created Massdrop. I’ve been a Styleforum member since 2011, and I’ve often been a part of those groups that are looking to put together something unique.

massdrop styleforum allen edmonds unlined suede chukka boot

That’s me, wearing the Massdrop x Styleforum x Allen Edmonds chukkas we put together.

Here at Massdrop, our job is to work with community members and help them engage with each other to find the products they want. You may recognize us from our affiliate thread on Styleforum, where we share some of our community-driven creations. By getting the community to work together (like they often do already), we’ve been able to get them the quality products they want for a better price. We’ve also found that if we work directly with brands to create new products, we can do even more to get the community what they want. If you’ve spent any time on Styleforum, you know that the people here are quite discerning. Almost any product, no matter how great, will inevitably be met with “if only this aspect were different, this would be perfect.” With our collaborative projects, our goal is to work with the manufacturers of these products to “tune” them to the desires of the community and offer them at a great price, resulting in an exclusive product that caters to what the community’s wants.

When we decided to kick off collaborations in the Massdrop Men’s Style community, the biggest question was who to partner with. We wanted to work with a brand with a strong forum following, as well as in-house manufacturing. Allen Edmonds quickly came out as a ideal choice – they have a huge fanbase on forums and beyond, and are a great go-to for those just getting into fine footwear. And while the quality of their products is quite high, many of the designs are less catered to the hardcore shoe enthusiast. Which led us to the question: what if they made a shoe specifically for us, the community?

The next step was landing on a style to pursue for the Massdrop x Styleforum project. We decided on the unlined suede chukka due to its popularity, as well as the fact that Allen Edmonds had released a few models that were ripe for tweaking (you can find many threads on the forum discussing the pros and cons of Allen Edmonds models like the Amok and Mojave). I reached out to Fok and pitched the idea to him. He has a long history of partnering with Allen Edmonds on the forum, and was able to perform the critical step of getting Massdrop in touch with Paul, the CEO of Allen Edmonds, which got the ball rolling.

I worked with Allen Edmonds production and the Massdrop team to learn about what the community’s options were in terms of materials, design, and so forth. We started working on prototypes, and once I had some samples to look at I reached out to respected members on Styleforum. With their help, we were able to hone in on what exactly a forumite would want in these shoes. After a couple months of prototyping, we landed on a style we all felt was a winner, and from there it was pretty easy.

massdrop styleforum allen edmonds unlined suede chukka boot

As you can tell, a lot of thought and a lot of details went into making these.

The most important aspects that we worked on were the material and the last. For the the suede, we sampled a few materials from CF Stead’s Janus line, and quickly agreed that Janus calf was the right call, even with the increased cost. For last shape, we wanted to shoot for the middle ground and offer something with a comfortable round shape for casual wear, without being too shapeless. Allen Edmonds’ 511 last was the natural choice, and the fact that it fits most people well was the icing on the cake.

 

From there, it was simple – introduce the shoes to the Massdrop and Styleforum communities. The project went live last week, and we’ve since sold over 700 pairs. The best part, however, is that it’s just the beginning. With this powerful example of what happens when a brand partners directly with the community they serve, we’ll be able to continue bringing projects like this to fruition. Styleforum members are full of good project ideas, and we’re going to do our best to keep up.

The Massdrop Allen Edmonds unlined chukka is available for purchase here.


The Styleforum Journal is supported by retailers such as Massdrop. This article is sponsored content.