Classic patterned socks, such as argyle, dots and stripe, are timeless and are easy to work with. A bare ankle with a sharp suit is still considered outrageous in a business environment. This is definitely not advisable unless your intention is to shock and surprise your board members.
Neutral pants colour, such as black, dark grey, white etc. will safely anchor any bold sock colour or pattern that you add without clashing and looking odd. When you are feeling more confident with your sock colours and patterns, feel free to change it up, mix it up and style it up. As long as both socks match each other and they are hole-free (and clean!), the styling is unlimited.
Different shoes will often require different socks, so mid-calf socks, the workhorse of your sock drawer, might not always be appropriate.
Hot days call for shorts, yet you still need to wear shoes. The predicament is evident. Going without socks could be an option, but sweaty feet are definitely not. Socks are essential here as they will protect your feet and your shoes from moisture and odour, even if the socks are no-shows. If you are wearing sandals, flip flops or any other kind of open shoes, there can be no socks. Just don't. The fresh air on your feet will be enough of a reward.
Important to note here, a dress sock in a finer fabric such as a Lycra or silk will not work well with a casual look. This is where your regular cotton or blend socks will be more effective in pulling an outfit together. At the same time, you should be avoiding a really thick, hand knitted winter sock with shorts, unless you are a game ranger. If you are wearing white athletic shoes, choose a white cotton ankle sock – or black cotton socks with a black shoe - so it looks like a deliberate sporty match. If you are brave enough to wear old-school tube socks, try and match the stripes on the top edge with your shoe colour.
Slouched socks are not cool now and they weren't cool in the 1980's. They look untidy and ill-fitting. Pull your socks up the whole way, the natural shape and elasticity of the sock will do its job and stay pulled up. If your socks are slouching even though they've been pulled up, it’s a sign that the elastic has perished and they need replacing as soon as you can get to a department store. Even better, shop online and get your socks delivered to your door.
Socks should not be folded or rolled as they just add bulkiness to your ankle and will look sloppy.
Loafers, suede shoes, or desert boots with shorts will all look good with invisible or no-show socks. This is the easiest option, but as we all know, easier isn’t always better. Bolder mid-calf socks will also work well, as well as athletic socks. Short ankle socks or long black socks are not a winning combination in this case, despite their recent appearance on the runway. From experience, what happens on the runway should often just stay on the runway.
Pairing your shoes with a sock of a matching colour will be a very safe casual choice. If you are bold enough to pull off wearing bright socks with a minimalist outfit – white or plain coloured tee-shirt with chino shorts – you can probably get away with it. The added bonus here is that you will get away with wearing the same outfit for a couple of days in a row as long as the socks change each day. Especially great on a holiday where packing space is a consideration.
For casual occasions, such as parties or going out with friends where you will be wearing jeans or chinos your shoe will generally dictate what sock to wear. Dark blue denim with a narrow leg that’s rolled up a couple of times, paired with a suede shoe will look fabulous with a bright sock. Try and keep your shirt either neutral or toned to match.
If you are wearing a really eye-catching pair of cowboy boots, or metallic shoes (it could happen!) avoid a statement sock as the shoes will be enough of a comment. In that event, make sure your socks are either very neutral and match your pants, or cannot be seen over the top of your boots.
Avoid pattern matching in your look. Stripes and stripes or dots and dots are a no-go. A green shirt with blue dots will not match green socks with blue dots. It looks contrived and deliberate and not in a good way. In that case, pick a solid colour for your socks. Pair the dotted shirt with a bright blue or green pair of socks.
Novelty socks with fun prints can show up your playful nature in the most formal situation. A fun repeated pattern, or a character from your favourite cartoon, can add a quirky twist to your outfit and take the bored out of board meeting.
Take a leaf out of Justin Trudeau's book. Serious business, such as running a country, can still have fun moments that lighten the mood. Mr Trudeau is well-known for his love of fun socks, often showing them off and making them something of a trademark for himself. He shows that he does not take himself too seriously and is not afraid to exhibit his sense of humour.
Despite their role in your daily routine and dress, you too can have fun with shapes, textures, colours and styles of socks. Let your socks be the star of your well thought out ensemble and save your frown lines for more serious matters, such as when is it acceptable to eat a well-done steak.
Doing the sock thing right will show that you are comfortable having fun with your look, after all, it's only socks!