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How to invest in a good pair of leather shoes

Trade in your sneakers for high quality footwear that lasts. Plus, what leather shoes I'm currently enjoying, and more!

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street night live
Oct 07, 2025
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“Sneakers are dead” is a topic that continues to be talked about a lot. It comes in waves, but right now it feels like we’re back on hating sneakers. I personally don’t agree with it because this narrative is mostly occuring online. If we go outside and take a look at what’s on people’s feet, then the answer is quite clear—sneakers are all around us and always will be.

Still though, we can’t deny that there’s been a bit more buzz around more grown up, typically leather in nature footwear that’s built to last. A lot of people I know are currently trying to find something a bit more serious themselves because a sneaker just doesn’t cut it on certain days.

I’ve also been hearing a common theme lately; shoes aren’t cheap these days, so why not spend a bit more and get something that’s nicer and that will also last longer?

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Derby, loafer, oxford, monk and other more experimental styles are all going to be great choices for when you want to put away your sneakers this fall. While they are ideal for the office setting and for that special event in your life, they can also be worn casually with the right outfit—I personally like wear my derbies with a high-quality sweatpant.

It may seem like a clash of themes that actually end up meeting in the middle when worn together, creating unique cohesiveness that lets you get away with wearing sweatpants outside more often. It’s that balance of chic and leesure that’s really attractive when done right. If you’re going with this stylistic approach though, then you have to make sure that both your footwear and sweatpants are crisp and high quality.


Anyway, so what makes a leather shoe worth the money? In today’s newsletter we’ll go over things I look for before dropping big money on footwear, some footwear recommendations I’m enjoying right now, and un-gatekeeping a brand that’s making affordable lambskin footwear in Europe.

Today’s recommendations

Because a good leather shoe costs money, this is an investment that you need to do some research on. Long-term, spending more on something that’s built well will always be the right option.

While it’s obviously important to buy something that you find visually appealing, one of the most crucial parts in any leather shoe purchase is the leather itself. Different leathers will give you different experiences, and knowing what you’re looking at will help you narrow down your purchase. There are a handful of leathers like cow, lamb, deer, and more, but the ones that I tend to stick to the most are:

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