A great pair of boots or shoes will never go out of style. We're not talking about "heritage" and the traditions of #menswear, but if something looks good, wears great, and can be worn on a daily basis, chances are it will become one of the favorite pieces in your wardrobe. Oak Street Bootmakers' Chicago location lets it take advantage of the best elements in the shoemaking world. The brand uses local Horween leather, and sources its footwear to Maine to be constructed. Really, there isn't a better combination. But most importantly, the brand's boots and shoes are something that anyone can wear. It just released new pairs of Trench Chukkas and Oxfords that are made from Horween's chromexcel leather—to give the shoes a slightly distressed, but totally superior finish.

You might tuck your brown shoes away until fall hits, but the lighter shade of each of this footwear will allow you to wear it even as it gets a little warm out. And hey, there's always brisk summer nights. Get your stacks up, nothing this good comes cheap. Check the brand's e-commerce shop for further details.