The uncomfortable truth when it comes to loafers is that any worth wearing are usually an investment. This means finding a pair made in Italy for under $250 was unheard of—until Astorflex came into the picture. Their Dartflex is a moc-toe loafer designed to continue conforming to your foot with each wear. The bovine leather is thick yet supple on the interior for comfort, and the outsole is leather to add classic looks and extra durability. From summer weddings and jeans to office looks, these will look good with anything and will age even better.

I like HOKA shoes, but this pair are by far my favorite. I'm a less is more kind of person—including branded logos—and these are sleek and understated. But beyond looks, the shoe's technology is insane. The quick-lace system is convenient and looks nice, and the aquaguard zip (which seals out water) is flawless—stylish and functional, protecting against all-weather elements. The ripstop mesh also gives the shoe extra durability to wear off-road or whenever it rains. The telltale sole from the label makes for a comfortable and smooth ride throughout the day, and while the shoe is on the chunkier side, I've been rocking some cargo pants and fatigues with these, creating a juxtaposing fit.

If you're looking to update your summer canvas kicks with something more elevated and ethically made—Veja's new Wata II sneakers are the answer. The shoes are made in Brazil from 100% certified organic cotton, and the soles are crafted from 40% Amazonian rubber and 10% recycled rubber. A toe cap ensures your feet are stable and comfortable—these are the types of shoes you continue to reach for throughout the warmer months—the only question remains, socks or no socks?