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There are some outfits that stick with you, some you can’t quite shake from your memory. One outfit I can recall with clarity was worn by a friend a couple of years ago, the ensemble in question consisting of a vintage hockey jersey, shorts and pristine tassel loafers he had just scored at L Train Vintage for a mere $20. It may sound like a strange amalgamation of clothing, but it was one of those outfits that just seemed to work.
Yet there was one facet of the look I found myself fixated on, the reason the look is planted in my memory — it was the combination of shorts and loafers. Because it wasn’t chino-style shorts he was wearing, but rather nylon athletic-style running shorts paired not with an equally athletic shoe, but leather tasseled loafers.
When you Google “shorts with loafers,” the image results are less than inspiring; little variety is offered amongst the the overwhelming images of guys in oxford shirts, chino shorts and loafers. Where are the men brave enough to break the arbitrary rules of what can and can’t be worn together? Pairing loafers, shoes often considered somewhere between casual and dressy, with shorts typically reserved for lounging or athletic activity, goes against everything we were taught when it comes to getting dressed. They’re too combative of styles that will never be able to work in harmony, people will declare. Well they’re wrong, for I’ve seen the combination work with my own eyes and all it takes is the right shorts, loafers and a willingness to step outside of one’s comfort zone.
Just think, you could be that guy who’s cool and confident enough to pull off something inconceivable for many, and maybe even inspire others in the process. Your styling capabilities will prove to others that you’re not afraid to take risks or step outside the confines of what are considered to be fashion do’s and don’ts. It’ll also provide a reprieve from the monotonous (and expected) pairing that has come to be athletic adjacent shorts with sneakers. And in a time when casual and loungewear still reigns supreme, the addition of a well-made loafer to an otherwise basic outfit of shorts and tee will be a subtle yet noticeable upgrade, and give you the sense of actually being dressed, a feeling that’s largely been lost in the current climate.
Below are 5 different pairings of casual, athletic style shorts and loafers, some more advanced than others, but all offering a much needed refresh on the shorts and loafers silhouette.
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.
Standard Cloth 3″ Oliver Nylon Short
Nisolo Alejandro Woven Slip On
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.
A24 Gym Shorts
G.H.Bass & Co. Larson Super Lug Basic Weejuns
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.
Outdoor Voices High Stride 5″ Short
Scarosso William Loafers
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.
Aime Leon Dore Tonal Sport Short
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.
Tracksmith Session Shorts
Allen Edmonds Cavanaugh Penny Loafer
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