Why You Should Spend More on Shoes and Less on Everything Else

I've owned the same leather loafers for eight years. They've been resoled once, polished more times than I can count, and they still look better than most shoes I see on people who buy new ones every season. That's the argument for investing in shoes in a single sentence. Fast fashion clothes are one thing. Fast fashion shoes are where you actually lose money, because cheap shoes wear out on the inside before they ever fall apart on the outside, and uncomfortable shoes don't get worn at all.

Shoes are the one category where quality translates directly into cost-per-wear in a way that's genuinely mathematical. A $400 loafer worn 200 times costs $2 per wear. A $60 loafer that hurts after an hour and dies in a season costs more than that. The math is uncomfortable but it's real.

The leather loafer

This is the single most versatile shoe in existence and I will not hear otherwise. A good leather loafer in black or cognac goes with jeans, trousers, midi skirts, dresses, and shorts. It works for work, weekends, and dressed-up evenings depending on what you put with it. The chunky-soled versions that have dominated the last few years are particularly forgiving because the extra height works with nearly every hem length.

When shopping for leather loafers (opens in new tab), look for a leather upper (not bonded leather, which is essentially cardboard with a coating), a leather or rubber sole that can be repaired, and a last shape that suits your foot width. Narrow feet suit the classic Gucci-style horsebit. Wider feet do better with a more relaxed round toe.

Brands worth the spend: Grenson, Penelope Chilvers, Church's, and on the more accessible end, Clarks' higher-end styles. If the budget extends to designer, the Gucci Princetown mule or the Prada lug-sole loafer are the ones that have earned their reputation rather than just their price tag.

The white leather sneaker

The investment case for white sneakers is slightly different. You're not buying these to last 20 years. You're buying them to look genuinely clean and well-made for the two to three years before they become unavoidably grey. Cheap white sneakers yellow fast and the material doesn't clean well. Quality ones stay white longer because the leather or canvas is denser, takes less surface dirt, and actually responds to cleaning products.

Common Projects Achilles is the reference point, but Golden Goose (if you can get past the deliberate distressing), New Balance 327, and Veja V-10 all hold up well. The key quality indicator in a white sneaker is the sole: a thick, well-bonded rubber sole won't separate from the upper the way cheap ones do. Press on the sole at the toe. If it flexes immediately, the bond is thin.

The leather ankle boot

A leather ankle boot (opens in new tab) in black or dark brown is the shoe that earns money back in effort saved. It goes with jeans, mini skirts, midi dresses, tailored trousers, everything you own for seven months of the year. The heel height matters: a low block heel or Chelsea boot profile is more versatile than a stiletto ankle boot, and more comfortable for the distances you'll actually walk.

Look for full-grain leather, a Goodyear welt or Blake stitch construction (both mean the boot can be resoled), and a lining that isn't just foam. Sam Edelman and Steve Madden are fine at entry level, but Sam Edelman boots won't last more than two seasons. Rag & Bone, AllSaints, and Madewell's leather styles sit in a reasonable middle ground. For something that will genuinely last a decade, Tricker's, R.M. Williams, and Blundstone's leather styles are worth the money.

Care that makes the difference

The single most effective thing you can do for leather shoes is apply a good conditioner twice a year and cedar shoe trees after every wear. The trees maintain the shape and absorb moisture. The conditioner prevents the leather from drying and cracking. A $15 tin of Saphir conditioner applied twice a year will extend any leather shoe's life by years.

Find a good cobbler before you need one. Getting new heel tips every couple of years is cheap. Waiting until the metal underneath has ground down into the sole is expensive. The shoes that look terrible on people are almost always shoes that haven't been maintained, not shoes that cost less. Investment shoes are only an investment if you treat them like one.