Loafers and khakis are a classic combination. However, if the thought dredges up bad memories of secondary school uniforms, fear not. These glossed leather, barbed-wire embellished loafers by Burberry are top of their class. Paired with cargo pants from Rhude and a soft blazer by Jacquemus, the effect is collegiate-inspired but with more swag.

Black and white loafers have a 1950s appeal that you can carry through your entire outfit if you’re in the mood to look clean-as-heck. These penny loafers hail from our own line, Mr P., and are crafted from calf leather and sport a durable Vibram sole. Keep your denim slim and short (here, we’ve chosen a Gucci pair) and your striped shirt tucked. Finish with a suede jacket from TOM FORD, a timeless addition to any outfit.

Yes, with shorts. Loafers, styled correctly, can dress up a warm-weather look with ease. Simple chino shorts, like these from AMIRI, are a smart choice, as are these sturdy, rubber-soled shoes by Yuketen. On top, we’ve chosen a KENZO button-down shirt layered under a roomy, cropped denim jacket from The Row. These stripey socks from Beams Plus and a cap from KAPITAL complete this look.

Meeting friends at the pub? Heading out to run errands? You can, and you should, wear loafers with your sweatpants. Just make sure the sweatpants are clean, tidy and cool like these from Acne Studios. And pair them with a button-down shirt (we like visvim’s plaid option) for a bit of added polish. Add classic tasselled loafers from G.H. Bass & Co., white socks and a raincoat and you look as put together as if you were wearing denim, except you’re more comfortable.