Let's be frank--like Bob Dylan wrote, "Behind every Beautiful thing, there's some kind of pain." Wearing fancy high-heeled shoes is going to involve a measure of discomfort. Part of minimizing the pain factor is picking the "right" shoe for you. Before torturing your toes in a pair of towering pumps or writing off heels altogether, consider the following words of wisdom and try a different approach. Let me know what works for you!
Picking the Perfect Pair
Emma's guide to high heels from this UK Daily Mail article
Know your Limits. Before you even leave the house, find out which height suits you best--use the heel height test (above). If your foot naturally remains at a right angle to your outstretched leg, or you cannot bend your foot forward from a right angle, you may have a low ankle-joint access and flats may be best for you. Otherwise, the distance between the heel of your foot to the invisible line forming a right angle from the top of your toe is the maximum heel height you should prance around town in.
Get Measured. Most people have two different sized feet! Go to the shoe section of a reputable department store and have both your feet measured. Remember that European and Asian sizing is different than American sizing--you may want to get measured for those as well. Otherwise, use a conversion guide, like this one to get a rough idea.
Try before you Buy. Different brands have variable sizing. Now that you've had your feet measured, try half a size up and down in the shoes you are considering, before committing with your wallet. The end of the day is usually when your foot swells and consequently the best time to try on shoes for true size. When you test out the heels, put both on and take a few laps around the aisles. Definitely try out non-carpeted surfaces, where possible.
Heels for your Body Type
A sample of shoes from my closet!
Pointy toe shoes subconsciously add length. Remember to leave enough room for your toes! Pumps are a standard go-to for work and simple styles/solids will stay in style "forever." Wedges provide good weight distribution for extended excursions. A V-shaped vamp (consult Part 1 to brush up on shoe anatomy) will visually elongate your toes and create a longer look. Ankle straps can add a subtly sultry component to spice up your outfit.
Petites benefit greatly from stilettos and narrow strapped slingbacks. Peeking toes and nude or neutral colors allude to length, and heels elongate the physique. However, avoid clunky wedges or chunky heels--they tend to create a visual anchor. Heel heights over 3.5 inches may cause the body to look disproportionate.
Contrasting shoe and pant colors will make short legs appear shorter. Likewise, chunky shoes add weight and T-straps accentuate width--neither of which are particularly flattering. Stick with open toe shoes, pointy tips or stilettos... and match your shoes to your pants.
Women who are already blessed with height should stick to kitten heels and flats for both comfort and style stimulation. Where sharp-toed shoes magically "lengthen," round shoes ground overwhelming height and minimize large feet. Contrasting shoes can dress up any outfit--try it out!
Thick Ankles or Athletic Calves
Knee-length boots are aesthetically slimming for those with larger calves. Well styled platform shoes provide balance. Avoid ankle straps, ankle boots, stilettos and cuts that attract attention to the ankle/calf area. A good alternative is a pump or a slingback--they make your legs look longer and therefore, slimmer.
Round toe shoes are best for wide feet--the shape offers roomy comfort for toes and reduces width. Brands like Cole Haan and retailers like Nordstrom offer wide width sizing. Avoid pointy silhouettes, instead, try rounded demi-wedges for a little bit of height.