Shoe shopping should ideally come at the end of the day, when you’re a bit tired & your feet are swollen from walking around for hours. This is for a couple of reasons. One is that with your feet swollen, you get a better idea of how the shoes are going to fit. The other is that when you’re a bit tired & worn out, you’re less likely to fall in love with a pair of shoes & buy them with little to no regard for their comfort level. (Yes, I’m looking at you!)

Here are some other tips…

Heels
If you’re interested in buying a pair of heels, the most important thing is to make sure that there is enough support under the balls of your feet — where your toes join the rest of your foot. The real test of this is to push down on the shoe bed, to see how it feels. If it’s hard & inflexible, those shoes are going to kill you. What you really want is a springy base to help absorb the shock of pounding the pavement. The best possible scenario is one where you press down upon the shoe bed & your hand bounces right back up again.

Flats
There is an assumption at the moment that all these people wearing ballet flats are walking around on clouds of air, in utmost comfort, etc. It is hogwash. Most of these fashionable flats have NO arch support, which is such a killer. If you’re going to buy flats, go shopping with a set of insoles in your bag. Put them in the shoe when you try it on. Initially, yes, it will be rather snug, but after a while the shoe will soften & you truly WILL be walking around on clouds of air, in utmost comfort, etc.

Soles
You should check these to make sure you’re not going to be slippery-sliding all the way down the street. The idea sole is rubbery with grooves. If your shoe’s sole is completely flat, you are in danger. Take it to a shoe store & get another sole attached!

Please note: All shoes need arch support! If you have a high arch (like I do), you will find most shoes are super-painful & that as you shuffle around the city, crying out, a sad man with a violin may start following you, playing a tragic ditty. This is not a good look. Do yourself a favour & buy some good insoles! Okay?! Okay!

Extra For Experts:
The Manolo has some wise words from Cary Grant on buying shoes. (Also read the comments, I luh-luh-looove them!)
SoYouWanna buy a good pair of sneakers?