The Fine Art of Going Sockless

The sockless look is very much in fashion at the moment.  It’s all over the place, from glossy magazine ads to TV to runways.  J.Crew, very much the bastion of today’s classic American menswear, has its models sporting Alden bluchers, vintage jeans and no socks.

On the formal wear front, Thom Browne has made the suit and sockless look part of his brand’s entire message.  What does all this really mean for everyday wear in real life?  how does one actually pull off the whole no-socks thing?

For starters, there are particular pieces of footwear with which one should never wear socks in the first place.  Deck shoes, those classic American Sperry Topsiders for example, should never come within a mile of a sock.  Even if it’s 10-below, one should always go bare ankled.

On the casual side, simple leather or canvas sneakers, aka trainers, look best without socks as well.  As with the deck shoes above, sneakers hail from a sporty, outdoors lifestyle and naturally fit with an equally sporty no-socks look.

These are the obvious choices of course; shoes that were never really meant to be worn in a formal or dressy context.  They fall into that classic zone of being timeless rather than fashion – you almost don’t even have to think about it.

The fuzzy area begins to form when we move in the direction of town shoes.  These are the shoes we wear in a more formal, often business context. We start with bucks – be they white, saddle or dirty.  Bucks, back when my father was at Yale, where more  of  the casual sporty shoes of the day.  Today, they are semi-formal dress shoes right at home in the office.

In warm weather I typically wear my bucks without socks.  There are a few rules for this; I have to be dressing in a generally casual manner or at least not with a formal business purpose.  I’ve seen guys in Boston wear bucks with khaki shorts and a worn out oxford – a great look worthy of Take Ivy.

Loafers and slip -ins are another category of near-dress shoes that adapt well to going sans-socks.  Especially in warm weather, sporting some nice cordovan slip-ins from Brooks Brothers paired with heavy linen trousers, a banker striped shirt and blue blazer, you have an ensemble that is pitch perfect.

The same goes for classic penny loafers or driving shoes.  In fact, I don’t ever think I’ve ever seen a pair of Todd’s Gomminis worn with socks.  Alan Flusser recently showed me his new pair, in electric blue, and the first thing I thought was – how can you even wear socks with those?  It just doesn’t work.

Lastly, we get to the business shoe debate.  Although all the rage, apparently to show how clever and avante garde one is, wearing town shoes in a business environment without socks is exceedingly difficult.  I know, I’ve tried.  There are, however a few rules that will help you look a little less like a runway poser.

First, your suit or trousers and sport coat should be on the trim side and more fitted than a basic business ensemble.  Part of the message going sockless in a work environment is supposed to convey is modernity.  At least right now, that means fitted and ever so slightly cropped.  Have your trousers just touch or slightly break over your shoe; it should look crisp and clean.

This aesthetic mirrors the outdoorsy un-traditional business message your look is trying to convey.  Pleats and a deep break just won’t do.  Additionally, you should pair your shoe to the overall outfit.  Trim cap toe to slim cut formal suit or heavy wingtip to khaki pant and light sweater.

It’s like going tieless; you do not want to look like you simply forgot your tie.  Same thing with the socks.