The questions that arise and haunt you while you’re getting dressed infamously affect your wardrobe decisions; exasperated sighs from irritated boyfriends; and harsh reprimanding from whoever you’re late to meet this time.  But we understand, even if no one else does.  The woes of the fashion conscious are innumerable.  Risk doesn’t always bring reward.  And playing it safe can leave your ensemble feeling underwhelming.  One intimidating trend that seems to have this affect on women is socks with shoes – [insert dramatic instrumental].

The sock and shoe trend has been consistently popping up for a few seasons now.  It’s a great way to add a little extra something to an outfit.  And, truthfully, it’s an even better way to cheat some of your less than practical footwear into fall for a few weeks.  But the quandary around who, what, when, where, and how to wear this trend is confounding for some, and can’t make it past the front door like a house arrest ankle bracelet.  But we’ve put together a few tips to help you pull of this look without too much guess work.

The best bottoms are midi-length dresses and skirts, and cropped pants.  These will give the look the most modern feel.  Sheer maxi length skirts are great for using your socks to give a bit of pop color in your outfit, though short skirts can potentially give off an 80s or junior vibe.  Shorts are more ideal with thigh highs, styled in a modest fashion for a great daytime look.

The best shoes are pointy flats; dressy loafers; brogues; pumps; mary-jane-esq flatforms; platforms, especially peep-toes; and most ankle booties.  That may seem like every shoe, but it's not.  Rounded-toe flats will require a Barbie lunch box, and knee-length socks with boots may give us the impression you dvr iCarly.

The best socks to dress up a look are bobby socks, women’s trouser socks, opaque socks, thin cotton knits, or simply a snipped pair of stockings.  The idea is that they should be fairly thin.  We recommend sticking to solid colors, since prints will require more editing.  Socks are actually a great way to work color blocking into an outfit.

The best ways to style them are bunched down if they are tall.  Those that stop just under the calf can be chicly worn fully extended up.  However, it's best not to bunch your socks with flats to avoid looking as if you got into a tussle at recess. 

Done correctly, a great pairing of socks and shoes is a small feat in our untiring quest for an expression of individuality through personal style. Though, not to be understated, it's the little details about us that really tell people who we are.  Bravely trying new accents will speak volumes.