At first glance, loafers when the mercury drops sounds like a bad idea. No-one wants a chilly breeze whistling around their naked ankles, right? But it doesn’t have to be that way. Loafers are actually quite versatile and, as we’ve covered already, you can even wear them with socks! Take that, Mother Nature.

So what’s the best way to wear loafers when it’s cooler? First, you need the right loafers. Second, you need the right styling. Loafers are clean and minimal by nature, and they won’t work with every ensemble. You need to plan ahead and be smart. But if you get it right, you can extend the wearability of your favourite loafers year-round (not to mention earning some bonus style points around the office).

Let’s get this one out of the way. Yes, you can wear loafers with socks. No-one will arrest you. They just need to be the right socks. In general, you should be wearing either invisible ‘sockettes’ (like the SETH) or full-length business socks in navy or grey, which can be pulled above the hem line of your pants. The look you want to avoid is mid-length crew socks sticking out the top of your loafers, or (heaven forbid) woolly hiking socks.

The Candela Patent Black Loafers

Another big choice: do you pick socks that will blend in with the loafer, or stand out? For first-timers, we’d recommend muted sock colours like grey, navy, brown or black. Especially when it comes to office wear. White socks and loafers generally belongs in the 1990s, or in avant garde catwalk shows. Some guys like to draw attention to their socks with colourful patterns, or flashes of sky blue, salmon, purple, pink and orange. This can work, but again, it’s a risky play.

In general, these loafers should be slightly thicker, with a higher heel profile. Something like the ERIK is perfect. You can also experiment with metallic hardware (the CANDELA) or textured leather (the FERRIS). Darker colours like black, burgundy and chocolate brown are going to be easier to style in winter, so keep that in mind. Try a pair of black BENITO loafers with dark socks, a navy suit and thick woollen trench, or maybe the KEMP with chestnut brown socks, khaki chinos and a navy blazer.

Loafers are actually one of the most versatile shoes around. It’s one of the reasons you see them on every second pair of ankles. They can work with suit pants, tailored woollen pants, chinos or jeans. It all depends on the styling. A pair of cognac ALBERTO 2.0 penny loafers would look great under tan chinos (neatly cuffed), or even grey suit pants. In the colder months, think more about layers and texture. If you go with loafers and jeans, try a zip-through knit. Loafers with woollen pants? Maybe a loose chambray shirt, or a button-up shirt, neatly tucked.  

Loafers and a suit is one of the hottest business style trends going around. And for good reason. Sharp loafers really help balance your silhouette, knocking the starch out of that standard suit-and-tie combination. In the colder months, try combining your loafers with heavier knit suits in charcoal, black and dark navy. Throw in some matching leather accessories, like a good belt, and layer up with a woollen overcoat or trench. For socks, stick to the safer shades: black, grey, navy and brown. Some GIACOMO loafers with brown socks and a caramel wool suit is a great way to stand out around the office.

The Alberto 2.0 Black Loafers

Leave the suede loafers in the wardrobe during winter. The risk of water damage is just too high. Likewise, stay away from crazy patterned socks with flamingos or Garfield all over them. They tend to distract from the real hero – your loafers – and should only be used ironically. Other than that, loafers in winter are very forgiving. If you focus on mixing up colour and texture, and building layers on top, you’ll generally be fine. Use accessories like scarves and gloves, and pick jackets that elongate your profile: longer peacoats, overcoats and trench coats work best.