Oxfords
Simply put, Oxfords are all-around beautiful, classic shoes. Yes, it might take a guy who knows how to dress to pull these off, but if a guy can, it looks good. If you’re going for a light pair of these, keep your entire outfit relatively light or else they’ll stand out in a bad way. Luckily, Oxfords now come in a slew of dark colours that are perfect for every fall wardrobe.  Some guys can pull these off in shorts, but those guys are generally the more hip and urban ones. It never hurts to try it out (at home first!) but usually, wear these Oxfords with pants.

Loafers
Loafers are probably one of the best styles of summer or fall shoes for men. They are amazingly versatile and come in a ton of different styles and colours. They’re casual enough to wear with dressier shorts for the summer, but also great with pants in the fall.

People usually are a little more relaxed about dress code in the warm weather, so don’t be afraid to pull these out. You can also easily pair loafers with shorts or pants, especially if you are wearing fall-based earth tones.

Note: loafers usually don’t work with is the cropped pant. It just looks awkward and mismatched.

Keds
Canvas-style shoes are every man’s friend in the summer, but don’t be afraid to carry them into the fall too. The Keds style is easily recognizable, but for a reason. These shoes are quality shoes and are versatile. They’re comfortable, casual and look absolutely perfect with shorts or any type of pant.

Of course, stay far away from dressier styles when you don the Keds, but in any other situation, these can make your outfit. Don’t be afraid to try on bright colours or patterns. Keds can easily pull a boring outfit together.

Converse
Just like Keds, canvas Converse sneakers are also a great light footwear choice. Although they’re not as easy to slip on and off, and should probably be worn with socks, they’re also a universal item that just about every guy can pull off. Lower-cut Converse are perfect with shorts and especially cropped pants, while high-tops are an ideal choice to pair with pants. When it comes to shoes, Converse sneakers are the ultimate classic item in casual footwear be it summer or fall.

Pairing and Other Crises
The hardest thing about finding mens’ shoes is that many don’t know what style goes with which outfit. It’s not that hard, but sometimes, you just can’t pair crop pants with penny loafers. In the end, you just have to know what styles look and feel good on you.