Having covered the main theoretical issues on the subject of favouring bare ankles, it's time to get down to business on the more technical aspects. Assuming none of the previous "requirements" are a deal breaker, let's focus on what to consider to pull off the look in a seamless fashion - mind you, these are not set in stone "rules", simply suggestions.

SHOE TYPE

Along with the overall aesthetic of the attire, the main aspect to keep in mind is definitely whether the shoe type is suitable for a sans socks look. As a rule of thumb, more formal styles such as oxfords, monk shoes or brogues should not be an option, unless you want to portray a very italian, fashion forward ensemble - in fact, this has been a statement look amidst #menswear finest. However, if you find it a bit too much for your personal style and environment, then loafers will quickly become your best companion.  

Despite common belief, loafers are casual in essence, making them the go-to choice to wear without socks (even if there are some styles which are considered a bit more formal). Material and shape dictate formality, with suede being more relaxed and patent leather more refined. 

Other suitable options for wearing without socks are of course sneakers and boat shoes, with the latter almost demanding a tanned ankle. 

TROUSER LENGTH

This is one of the aspects that bear a striking influence in the overall look, with small differences portraying anything from outdated, to contemporary or hipster. When going sockless, the ideal trouser length should be sitting on top of the shoe, or slightly above, with no break - if you're ditching the socks at least show it!

INVISIBLE SOCKS

A critical aspect of not wearing socks is definitely comfort, especially if you're going for sturdier leather shoes - a long day's walk may cause sweating, bruising and discomfort. The best to prevent this is to wear invisible socks - these will keep the no-socks look while protecting your feet and increasing the durability of your shoes.

SHOE CARE

Finally, the best way to ensure your shoes will last longer and optimal hygienic conditions is to ensure proper shoe care. While this is a good practice overall, it's even more important if you're ditching socks as your footwear will absorb more sweat and dirt. Making sure you keep your shoe choices on rotation, leaving them to dry at least for 24h and using cedar shoe trees will increase they durability. You can also opt for a shoe deodorant, but if you go with shoe trees it shouldn't be necessary.