Never say we don’t answer the big questions here at Aquila. Loafers with socks. Is it ever okay? The short answer is…it depends. Socks and loafers have become kind of a controversial style choice. Some guys swear by socks. Others reckon they look terrible. Like everything else, it usually comes down to the overall outfit and accessories.

The reason loafers and socks are tricky is that loafers have a much lower, cleaner profile than your standard Oxford or Derby. They’re minimal and dressy by nature, and sometimes socks can spoil that toned-down look. One thing’s for sure: if you’re going to rock socks and loafers, they have to be the right socks. Woolly mountaineering socks do not belong anywhere near your loafers. You want thin cotton or wool, and usually a muted, no-nonsense shade, like black or navy. Save the crazy flamingo socks for special occasions.

So, can you wear socks with loafers?

The Giacomo Dark Brown Loafers

Before we jump into styling suggestions, let’s talk about sock length. With loafers, no matter whether you’re wearing chinos, jeans or suit pants, your socks need to be either fully pulled up (i.e. above your hem) or full trimmed down (i.e. below the top of the loafer itself). If you get caught in no man’s land, with the top of your sock visible below your pants, it’ll just look ridiculous. The idea is a solid block colour between loafer and pant – or nothing at all.

There are certain situations where socks and loafers make a lot of sense. Suits being the big one. Most guys don’t have the confidence to flash their naked ankles around the office, and there’s nothing wrong with some good quality socks between your loafers and your suit. In fact that’s how we’d recommend you wear them. Make sure you pick a shade that matches both the leather and the fabric. Plain-old black or navy socks will rarely steer you wrong, but burgundy socks with brown loafers and a navy or charcoal suit is a great way to add some subtle colour.

When it comes to loafers, styles like the ALBERTO 2.0 and BENITO are a good place to start, but for more formal occasions, you probably want some black patent leather loafers, like the ASCOTT. Our best-seller, dinner-with-the-Queen loafers, and they should always be worn with socks. Preferably plain black cotton dress socks. In fact, here’s a good rule: if you’re wearing loafers to any event where caviar is being served, socks are the way to go.

The more casual the loafer, the more casual the sock. That’s another good rule to follow. A suede loafer like the GIACOMO, for example, could be worn with crew socks, slim-cut indigo jeans and a cable knit. In that case, try to keep your socks and jumper in the same tonal range. Not an exact match (that can look a little odd) but close enough. Neutral sock colours like burgundy, dark grey, brown, khaki or navy are all solid choices. White and black socks are usually too stark for casual loafers, especially brown loafers (brown and black are rarely best friends). Loafers and white socks, in particular, are more of a counter-culture, Kramer-from-Seinfeld kind of statement.

Driving shoes are a close cousin of the loafer, and the same sock-versus-no-sock debate often creeps up here. The good news is, driving shoes are casual by nature, so you’ve got more flexibility in the sock department. Invisible ankle socks, cotton crew socks, patterned socks – they’re all okay. If you want to splash some polka dots and colour with our SENNA driving shoes, you can. It’s still a risky play, but it works.

If you’re dead set on eye-catching socks with driving shoes, keep the rest of your outfit fairly muted: lots of khaki, earthy greys, browns, navy blues etc. That way your socks will pop, which is the whole point. Something like our patterned SODA socks are a good halfway compromise. They’re fun, but not wacky.

The Alberto 2.0 Cognac Loafers

Loafers without socks (AKA ‘Sock Commando’) has become arguably the default way to wear them. Especially when it comes to jeans and chinos. This is the look you see in all the magazines: guys lounging around in pin-rolled chinos, penny loafers and bare ankles.

The good news is, this look doesn’t take much effort or skill. All you have to do is pick some smart-casual loafers, like the PORTER, GIACOMO or BENITO, and throw them under jeans or chinos with a nice, high hem (the pants should rest just above your ankle). The other big one is shorts. Loafers and shorts never, ever require a sock. Socks and shorts in general give off serious old man, retirement village vibes. The exception is crew socks and athleisure gear, which is totally fine.

But here’s the big question: should you ditch the socks all-together, or find a discreet alternative? Wearing leather loafers without socks is not something we generally recommend. Sweat builds up and affects the leather; it tends to smell; and you’re more likely to get blisters. Instead, why don’t you try…

Ankle socks (also known as ‘invisible socks’ or ‘sockettes’) are sort of the compromise position in the socks-versus-no-socks loafer debate. They’re a more hygienic option than going full sock commando, and most people won’t even spot you’re wearing them. These socks should, ideally, end below the heel of the loafer. That’s what makes them invisible. You can embrace the sock-less loafer trend, flash your ankles all over town, and still keep your feet dry and warm. Our SETH socks are the way to go here – they come in a grey and navy twin pack.

So, should you wear socks with loafers? Think about socks like pocket squares: they’re not for everyone, but some guys prefer them. A bit like pineapple on pizza At the end of the day, you should wear whatever makes you feel comfortable. Let you ankles fly free, or cover them up. It’s totally up to you.