A common fashion struggle is the desire to buy new pieces while the weather is stuck in last season. While we don’t mind another month or so of barbecues and sunshine, we’re already preoccupied with thoughts about which Italian shoes we will be wearing this autumn. That’s where great transitional shoes come in. You can go ahead and buy them now, style them for summer, and come autumn they are perfectly broken in and ready to pair with your favorite layering pieces. One of our favorite transitional shoes is the chukka boot. 

While there is no mistaking the versatility of the chukka in colder weather, it may be hard to imagine how to style this boot in the hot summer months—especially if your go-to pants style is of the short variety. Make no mistake about it, chukka boots can look pretty cool with shorts as evidenced here and here… but this style comes with a few stipulations. First: leave the jorts at home. Pair with nice, tailored shorts or not at all, gents. Second: maybe don’t attempt this style if your legs are on the shorter side. Having a slightly taller shaft, chukkas can cut off the length of your leg making them look stubbier than they really are. If you don’t want help making your legs look shorter, avoid the style pairing.

Since a lot of guys don’t even bother with shorts, we’d be remiss if we didn’t mention how awesome chukkas look paired with colorful chinos. It’s amazing how simply putting on a pair of comfortable pants in a color that isn’t of the neutral family can fool people into thinking you’re a fashion icon. Pair your fancy pants with a pair of chukkas and it will elevate the look even further. Since it’s still hot out, top off the look with a breathable, short-sleeved cotton Henley, a braided belt, and your favorite shades. We’re not sure how something so simple can look so cool, but it does.

Once the weather cools off, your chukkas can keep their place as a fixture in your leather shoe rotation. Pairing them with jeans, layers, and even a suit is an option for this classic style. Check out our advice on how to style chukka boots then stop by the Paul Evans store to buy your own pair.