How to shop for…shoes

Some things you might not think about

Alex English
Aug 10, 2019 · 6 min read

It may seem elementary and perhaps a bit presumptuous to write a post about how to buy shoes — I’m sure you’ve all bought plenty of shoes before and been just fine. But in my lifetime of shopping and amassing many shoes (and then paring back down again), I’ve learned a few things that now guide me whenever I’m buying footwear.

For any amount of walking, no hard leather soles

In dense cities, we all walk a lot. Even if we drive from place to place (or catch Lyfts or take mass transit), there is an increased amount of actual walking than in places that are truly car-oriented. I learned this moving from Florida to Italy, bringing with me many beautiful leather-soled loafers and boots and stomping all over those cobbled streets and miles across Milan.

Never in my life did I have so many blisters and eventually corns on my toes (ultra-sensitive hard callouses), to the point that I was buying all the gel insoles and bandages to keep my feet from incredible pain.

For a long time I looked down on rubber-soled shoes, either because they weren’t as elegant as leather-soled, or because I perceived them as lesser quality. Those are both mostly subjective assessments, and what I learned through trial was that for any decent amount of walking, rubber or foam is the way to go. Leather is inherently stiffer, less flexible, less shock-absorbing, and generally harder on the feet over time.

Many brands are making fewer hard leather-soled shoes because the world is becoming more casual. Or, they’re creating hybrids that have the traditional look of a leather sole with the comfort of a rubber sole. In any case, it’s imperative that when shopping for shoes, you consider where and how often you’ll wear them, and if comfort will need to take priority. When in doubt, err on the side of comfort, as there’s nothing worse than buying beautiful shoes you’re afraid to wear because they’re so uncomfortable.

Some shoes can be repaired/resoled, others are harder

Shoe repair is a charming and antiquated art form, though coming back in some fashion thanks to a renewed interest in hand crafts and some very tactile ways to make money and spend one’s days.

I love watching Bedo’s Leatherworks videos because they’re exhaustive in their gory detail of how a shoe (or handbag) gets deconstructed, refreshed with new materials, and then is put back together again. If you’re an ASMR fan, it’s also sorta sickeningly satisfying to hear him cut through leather or thread using an X-ACTO knife.

Anyway, most high-end leather shoes can be resoled (or generally given a decent rehab) by a talented cobbler, regardless of the type of sole they started with. There is however a limited possibility of prolonging a shoe’s life if the starting point is poor quality leather or fabric using lots of glue.

In some cases, even very inexpensive shoes can be repaired or resoled, but the job is made easier, less expensive, and makes better sense to a cobbler if the traditional materials and methods of construction are present (e.g. goodyear, blake, or other stitched leather construction with insole, midsole, and outer sole).

Which leads me to…

Invest in quality (and take care of quality) and you can keep shoes for a long time

By default, I am attracted to more expensive shoes, from a design, brand, and overall aesthetic perspective. These shoes tend to be higher quality, made with good materials and construction methods. I take care of them and they in turn last a long time, minus normal wear-and-tear. It’s that simple.

While not all “expensive shoes” equate to high-quality shoes, many do. On the other hand, there are plenty of brands making high-quality shoes that aren’t fashion brands with a big mark up, so it comes down to a balancing of any shoe’s look, overall quality, and estimated longevity. I have just seven pairs of shoes now vs. the 20+ I had previously, so the ones I have will get more wear more quickly than before. But they can also be repaired and refurbished for a modest cost ($25–30 per pair) or resoled ($80 or so).

I use cedar shoe trees in almost every pair of shoes I own, so they dry out in between wears and retain their intended shape. These are a good investment along with the shoes themselves.

Sneakers and casual shoes with white rubber soles — cleanable? Pre-treatment?

I avoid white rubber soles because I assume they will get scuffed and dirty, which they will without proper pre-treatment and some strategies for periodic cleaning.

There are plenty of sprays and DIY how-tos online about cleaning white soles or white shoes, none of which I have tried, but I may next time I encounter a pair of white-soled shoes I like. Many athletic shoes have white rubber or foam soles as opposed to black or “natural” which is a sort of light tan color.

Here are some resources I found useful:

So, white rubber soles = not something to be afraid of, but something to be aware of before buying.

Think about your default climate

I cringe whenever I see people wearing suede shoes or shoes with leather soles in the rain. Moisture like that will quickly ruin untreated suede uppers, and for leather soles (that come in contact with wet pavement), they will get water-logged and ultimately rot out. Not cute.

So in addition to comfort and style, think about your default climate. Is it dry, humid, hot or cold?

In San Francisco, it’s always a little chilly, so sandals are few and far between as a practical option. Sneakers are preferable, but not always the most insulating from cold.

In Los Angeles, because it can be much warmer, sandals are great. And, you often don’t walk as much as you drive, so you can wear dressier things.

In Florida, it rains all year long, especially during the summer, so leather and suede shoes are tricky at almost any time.

In any climate with a decent chance of rain or snow, go with rubber-soled shoes whenever possible.

Likewise, when you travel, keep in mind the climate of where you’re headed.

Think about what is most versatile to you, and what do you like most in a pair of shoes (for me it’s some height like a wedge sole)

There are plenty of interesting, attractive shoes out there. Only a few of them work for me, because I like a bit of height on a boot, loafer, or lace-up. Wedge soles are ideal.

All of the shoes I have now are slightly elevated and give me that power stance, which makes me feel good. Some people prefer thinner soles with little or no height added.

I also always make a point to assess how a shoe looks on my foot from the top, which is the view I’ll see when I’m wearing them. Are they too pointy, too wide and blocky? At some point you also have to enjoy that view, so it’s something to be aware of. For example: I like the Maison Margiela Replica sneaker, but think it looks awful on my foot from above so it’s always a pass.

The last thing I consider when it comes to versatility is color. The neutrals are always safe choices — black, brown, gray, tan, and white. They go with mostly everything. Maybe some earthy tones like navy, dark red, or olive. Otherwise I shy away from crazier colors that have limited or novelty appeal.

It’s all these factors that weigh on a potential shoes purchase, but they can be boiled down to: are they practical, do they feel good to wear, will they fall apart quickly, and do they work with my wider wardrobe?

Answering these questions before pulling the trigger will ensure a long happy life with a new pair of shoes ❤.

Alex English

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Writer, thinker, aesthete. Website:

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