1. Heel Height: Do not be overzealous with heel height, picking the right height will multiply the wear of your shoes by the 100s. I literally have so many pairs of cute booties that are just 1/2- 1" too high for the day to day wear. If I had picked something just a littttle bit shorter I would be wearing them all the time. Even a pair of Chloe booties I bought. I thought since they were Chloe they'd be amazing leather and really comfortable to wear... But at almost 5" high, I will definitely not be commuting to work in these any time soon. Therefor, buy a heel height that works for the occasion you're at most; work, running errands, going out,ect. Unfortunately, sometimes it's just best to be practical. One exception to this rule: If its a wedge... sky's the limit!
2. Shaft Length in flat boots: This is critical for having a flattering shape on your leg. Boots range from ankle to mid calf to full calf, to my favorite, over the knee! :) An ankle length flat boot is what I find to be the most challenging, I always go for a pointed or almond shaped toe in this style to elongate the leg. Otherwise I do not find this to be flattering. I like to have at least a little bit of height on the shaft of the boot. It's easier to tuck in jeans, and makes your legs look skinnier, since the boot is balancing out the thigh.
Also, I opt for a looser fit in shorter boots so that the boot looks wide and ur leg looks tiny! The higher up the leg the shaft goes, the more fitted it should be. Just make sure it's in a nice suede or sturdy leather that wont bunch up and add weight to your legs.
3. Leather Vs Suede Vs Faux: Surprisingly enough, I actually love Faux leather boots, as long as you can find some that look semi real. Real leather can require a lot of care and if not cared for properly you can easily develop skuffs and small tears. It's sad that most of my real leather boots fall apart faster that my faux ones. Still, I don't like to buy faux leather that looks plastic-y and cheap. I usually look for faux leather in black with a little texture- pebbled leather, or worn in a bit.
Suede is always my favorite! It looks rich, chic, and adds texture to a flat look. Especially if you're someone like me who is always wearing a leather jacket, pants or bag..you definitely don't want your look to be head to toe leather
4. Toe shape: This is simple. It must point! At least a little almond shape will do. But seriously, a little point on the toe can make your legs look 10x longer and leaner!