top: Madewell; skirt: Urban Outfitters; bag: Rebecca Minkoff; necklaces & cuffs: DANNIJO; platform sandals: Shuler & Sons (via anthropologie); flat sandals: Ally Lulu (old)

It’s the weekend. You’re preparing for a night out and you’ve assembled an outfit that is equal parts casual and cool- perfect for dinner, a bar or a party (or all three if you’re really taking the town). The sartorial decisions are almost complete and yet one remains…and it’s a doozy: go high or go low? I’m speaking of shoes and the choice between wearing heels and wearing flats. Initially it appears to be a simple selection and yet it’s riddled with complexity.

Both have their strengths. Heels are very flattering to the leg, they provide a boost for anyone vertically challenged (ME!) and generally help jazz up an ensemble. Flats are more relaxed, toning down an outfit to a more chill frequency and they are comfortable (this can come in especially handy if you find yourself on the streets at 2am with no taxi in sight).

The downsides to each really depend on what the other women at the event are wearing. If everyone else has gone with flats and you are in heels, it’s easy to look like you have made too much effort, are over dressed- any sense of coolness goes flying out the window.  On the other hand, if everyone else is in heels and you are in flats, it can feel like you are a child at the grown-ups table. Not to mention if you are petite, having the other women at an event tower over you in vertiginous shoes can feel slightly (or majorly) belittling.

I remember reading a magazine article years ago that advised that one should err on the side of dressing up too much rather than less. If you followed this strategy and found yourself in a bowling alley in a cocktail dress or other awkward situation, their solution was to pretend you had some more fabulous event to attend later in the evening. It seems to me that the success of this plan depends on the time of night it is employed (if you arrive at a party at 11pm, are you then supposed to pretend you have a black tie event that starts at 2am or can the ‘more fabulous event’ just be going home to bed?!) and it relies on your ability to keep up the fib as the drink count mounts (this is definitely not my strength).

In reality, the answer to heels or flats depends on the evening. I generally follow my gut-instincts and make sure that I feel good in whatever I’m wearing but I have found no surefire way of completely avoiding these sorts of footwear pitfalls. Let’s hear from you dear reader, am I the only one who stands in front of the mirror with a heel on the right foot, a flat on the left, turning side to side to try and reach a decision? Any advice on which one to go with? I’m all ears!