Everyone should be able to count at least one pair of Baggies-esque shorts in their summer wardrobe, but it’s time to view the everyday bottoms in a new sartorial light. Their possibilities for wear extend far beyond the couch or running errands. When paired with a shoe like these Nisolo woven slip ons, the shorts are elevated while the overall look remains casual. For those who still can’t commit to wearing traditional loafers with shorts, allow these slip-ons to ease you into the process, while still proving to be a much needed upgrade from your sneakers. As for the top, all that’s really need is a white t-shirt to effectively capture that cool, casual yet stylish essence.

Maybe you’re not a big loafer person to begin with or you find them a little too preppy for your taste. If that’s the case, consider this pair of penny loafers from the G.H.Bass, which offers an unexpected twist on the ever-popular Weejuns. The thicker, almost platform-like sole imbues the otherwise classic silhouette with a bit of punk rock flair. When paired with shorts like these basketball-style shorts (which are highly on-trend) from indie production company A24, the punk vibe of the loafers is only intensified. A look for those who truly want to push the boundaries and challenge the fashion status quo.

A pairing inspired by the look that started it all, and when it comes down to it, it’s really not that crazy of a combination. If these Outdoor Voices Rec Shorts were to be crafted from a cotton chino fabric rather than nylon, their pairing with these Asos tassel loafers would be a given. But it’s all a matter of getting out of the mindset that certain clothing items are allotted for certain activities — it’s a mindset that allows for little fun or creativity, one that restricts you and your closet. The black shorts still manage to keep the look relatively grounded, and from far away one isn’t likely to know they’re made of nylon, while still showing that you’re down to experiment.

When wearing something like a pair of bright blue shorts by Aime Leon Dore, it’s best to keep the rest of the outfit relatively simple. But instead of reaching for a pair of white sneakers, opt for these Astorflex loafers instead. They’re simple enough that they won’t draw too much attention while simultaneously garnering you respect from others for your unexpected choice. The rich caramel colored leather works in tandem with the oceanic blue of the shorts to create a palate conducive to summer. Feel free to take styling cues from this Aime Leon Dore model and top the look off with an equally bold, abstractly patterned shirt layered over a white tank, one of our favorite summer styling hacks.

Don’t be hesitant to lean into the preppiness of Allen Edmonds’ Cavanaugh Penny Loafers with this retro-esque pair of track shorts from Tracksmith. The combination of the navy shorts with the burgundy loafers is a preppy dream, while the choice of track shorts rather than chinos lends the look a fresher, much needed update. It’s a look that would fit in well on a 1970s Ivy League campus, if that’s the kind of thing you’re going for — and it probably should be. Pair it with a navy top or sweater a la this look via a young Harrison Ford. We've put in the work researching, reviewing and rounding up all the shirts, jackets, shoes and accessories you'll need this season, whether it's for yourself or for gifting purposes. Sign up here for weekly style inspo direct to your inbox.