Cheap Shoes That Age Well
Although I wouldn’t call it a “rule” for myself, when I can, I try to buy things that I think will look better with time, rather than worse. That is, after all, why most of us value full grain leather shoes over corrected grain ones. It’s not because they’re cheaper in the long run (because they’re not). It’s because high quality shoes acquire a beautiful worn in look that only good materials and years of wear can impart. Shoes made from corrected grain leather, on the other hand, look terrible new and even worse with time.
Unfortunately, shoes that age well are typically expensive. The exception to this is canvas sneakers, which always look better with a bit of dirt and grass staining. Think:
Converse Chuck Taylors and Jack Purcells
Vans Authentics and Classic Slip-Ons
Superga 1705 and 2750
Sperry Top-Sider’s striped CVOs
Tretorn Nylites
All of these retail for under $75, but can be had for less than $50 if you wait for sales.
The best thing about these shoes isn’t their price, however. It’s their designs. Most have been around for decades and their designs are hard to improve on. Take Maison Martin Margiela’s interpretation of Vans’ slip-ons, for example. The heavier look and feel of leather doesn’t evoke the airiness of summer like canvas, even if the design itself looks more luxurious. Similarly, Nigel Cabourn’s interpretation of Chuck Taylor All Stars has a nice retro feel, but truth be told, I think the standard model today is hard to beat.
You can wear these with any number of spring or summer ensembles. I often wear my Chuck Taylor high tops with a white t-shirt, leather jacket, and pair of jeans, and my Superga 1705s with chinos and a madras shirt. On a cooler spring day, the madras shirt gets swapped out for a sweatshirt and light parka. Neither of these feel like compromises over full grain leather shoes, and they’re appreciably much cheaper. It’s nice that good things don’t always have to be expensive. 

Cheap Shoes That Age Well

Although I wouldn’t call it a “rule” for myself, when I can, I try to buy things that I think will look better with time, rather than worse. That is, after all, why most of us value full grain leather shoes over corrected grain ones. It’s not because they’re cheaper in the long run (because they’re not). It’s because high quality shoes acquire a beautiful worn in look that only good materials and years of wear can impart. Shoes made from corrected grain leather, on the other hand, look terrible new and even worse with time.

Unfortunately, shoes that age well are typically expensive. The exception to this is canvas sneakers, which always look better with a bit of dirt and grass staining. Think:

All of these retail for under $75, but can be had for less than $50 if you wait for sales.

The best thing about these shoes isn’t their price, however. It’s their designs. Most have been around for decades and their designs are hard to improve on. Take Maison Martin Margiela’s interpretation of Vans’ slip-ons, for example. The heavier look and feel of leather doesn’t evoke the airiness of summer like canvas, even if the design itself looks more luxurious. Similarly, Nigel Cabourn’s interpretation of Chuck Taylor All Stars has a nice retro feel, but truth be told, I think the standard model today is hard to beat.

You can wear these with any number of spring or summer ensembles. I often wear my Chuck Taylor high tops with a white t-shirt, leather jacket, and pair of jeans, and my Superga 1705s with chinos and a madras shirt. On a cooler spring day, the madras shirt gets swapped out for a sweatshirt and light parka. Neither of these feel like compromises over full grain leather shoes, and they’re appreciably much cheaper. It’s nice that good things don’t always have to be expensive.