Ensure that you have a number of sock styles to choose from that work well with multiple outfits
Getting your colourful sock collection started? If you’ve never worn socks that don’t match your trousers before (or worse, if you’ve been wearing white socks no matter what your trousers look like!), start your new adventure at any decent menswear store. Most will have at least a few selections of simple, traditional patterns like argyle.
From there, head to the internet and start indulging your newly found appetite for trend setting socks. Think in terms of the outfits you’re likely to be pairing your socks with. For example, look for colours that complement your favourite shirts and jackets, or that work well with your existing collection of pocket squares.
Sometimes, you might specifically want to wear coloured socks; beyond just enjoying them for their own sake.
When you want to liven up a simple outfit, a pair of unique socks turns something like a jeans/T-shirt or khakis/collared shirt combination into something that seems a little more deliberate. It’s like a pocket square in a jacket; it tells people that you don’t look this way by accident, and that you’ve put some thought into your outfit.
For the ultimate in colour-coordination you could even match your socks to your complexion!
Not everyone likes to keep their shoes on all the time; even when doing business. In countries like Japan, shoes are often removed for meals, and even for drinks. If you have reason to think that you’ll be doing business in your stocking feet, go ahead and make it fun; so long as you’re not planning on doing serious business with conservative people! You don’t even have to go to Asia for sockless situations; anything from a locker room, to a corporate spa, to a meditative retreat might end up with you shucking your shoes and bearing all.
Beyond these specific situations, there’s also the simplest and best time to wear coloured socks: when you feel like it.
As long as you’re putting some thought into how you’re strutting your gussied-up ankles, there’s no reason at all why you can’t play around with your socks, and have fun with your basic, day-to-day, outfits. And above all, have fun. Life’s too short to never enjoy bright colourful socks.