I have a very strong separation between work shoes and non-work shoes. For work, I wear Sensible Shoes. Period, because otherwise I won't feel like doing anything but soaking my feet at the end of the day, and that's been true since I was in my 20s. (When I was a teenager I could wear heels all day. But when I was a teenager I was also eating-disordered and I can only conclude from this that when I was a teenager, I did not listen to my body.)
Seriously, for being on your feet most of the day you want sensible shoes. They don't have to look like your grandma's shoes. Most of mine are Doc Martens' maryjanes. You can even wear those with lolita if you pick the right socks. (I have done this.) Look for shoes with a little padding on the heel because what causes heel blisters is the hard edge of the heel rubbing against your heel and achilles tendon. Make sure they are deep enough to accomodate your foot because another source of blisters is when the shoe opening is tight and cuts into your foot. It's best to try shoes on at the end of the day when your feet are a bit swollen; if they're comfy then they'll be comfy all day. I would recommend trying on shoes in a store (but not buying more than one pair at dept store prices) and then buying shoes on ebay once you know what size you are. Unfortunately sizes vary by brand. (I love the way Irregular Choice shoes look but have sold or given away most of mine because I have real trouble with their sizing--39 is too snug, and 40 falls off, wth.) Other good brands for work shoes are Trotters and Ros Hommerson. Drew shoes are comfortable but most of them are ugly as fuck; I need to get the one pair I have that are pretty and I like fixed stat. I also hear good things about Danskos but I don't own any.
I love Everybody by BZ Moda (not Everybody by alife) shoes lots, but the heels are not work-suitable, only the flats.
Ankle rolling is a danger with lower heels, it's true. Little Victorian boots don't cause this problem so much, but that's because the boot comes over your ankle and supports it. I can actually wear little Victorian boots to work. But I will never again wear them to the Folsom Street Fair. (omg agony--don't do this--the streets south of Market are painful to walk on unless you have nice thick soles on your shoes)
There are very few professional looking shoes or dressy shoes (other than sandals) that are comfortable to wear without socks or stockings. Very very few. That's why they make those nylon minisocks that cover only the part of your foot that goes inside the shoe.
Foot Petals (googlable) are also nice for shoes that rub. They're little pads that you can stick inside your shoes.
In addition, one of the reasons I hate peeptoe shoes like burning is that aside from the fact that I don't really want to see most people's toes and don't find it sexy at all, wearing them is awful because the heel tends to force your whole foot down and into the toe opening. If you like those, which is a total matter of taste, they should probably not be Work Shoes.
I've heard good things about mineral makeup and plan to try it soon. I hope it works.
Getting a manicure will put an end to the nail biting, although if you get fake nails you have to have the salon trim them and fill in the bottom as they grow. Fake nails are, well, fake, and I only had them once because I didn't feel they were clean enough for hospital work, plus they were hard to type with, but my real nails are short because they split easily into layers and then tear, so if I want to have them long at all they have to be fake. However I'm told that the advantage of fake nails for kink is that the edges are smooth, so you can scratch without drawing blood, and if you put your fingers inside someone else's body the nail edges will be smooth not jagged, meaning they will tear neither your latex/vinyl gloves (if desired) nor your partner's innards. If I was dating someone who was into nails I'd get short fake ones and keep them short with fairly frequent salon visits because my own won't grow that long (srsly, the number of times I have had to trim a nail with office scissors because it split boggles the mind) and are very sharp.
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I have a very strong separation between work shoes and non-work shoes. For work, I wear Sensible Shoes. Period, because otherwise I won't feel like doing anything but soaking my feet at the end of the day, and that's been true since I was in my 20s. (When I was a teenager I could wear heels all day. But when I was a teenager I was also eating-disordered and I can only conclude from this that when I was a teenager, I did not listen to my body.)
Seriously, for being on your feet most of the day you want sensible shoes. They don't have to look like your grandma's shoes. Most of mine are Doc Martens' maryjanes. You can even wear those with lolita if you pick the right socks. (I have done this.) Look for shoes with a little padding on the heel because what causes heel blisters is the hard edge of the heel rubbing against your heel and achilles tendon. Make sure they are deep enough to accomodate your foot because another source of blisters is when the shoe opening is tight and cuts into your foot. It's best to try shoes on at the end of the day when your feet are a bit swollen; if they're comfy then they'll be comfy all day. I would recommend trying on shoes in a store (but not buying more than one pair at dept store prices) and then buying shoes on ebay once you know what size you are. Unfortunately sizes vary by brand. (I love the way Irregular Choice shoes look but have sold or given away most of mine because I have real trouble with their sizing--39 is too snug, and 40 falls off, wth.) Other good brands for work shoes are Trotters and Ros Hommerson. Drew shoes are comfortable but most of them are ugly as fuck; I need to get the one pair I have that are pretty and I like fixed stat. I also hear good things about Danskos but I don't own any.
I love Everybody by BZ Moda (not Everybody by alife) shoes lots, but the heels are not work-suitable, only the flats.
Ankle rolling is a danger with lower heels, it's true. Little Victorian boots don't cause this problem so much, but that's because the boot comes over your ankle and supports it. I can actually wear little Victorian boots to work. But I will never again wear them to the Folsom Street Fair. (omg agony--don't do this--the streets south of Market are painful to walk on unless you have nice thick soles on your shoes)
There are very few professional looking shoes or dressy shoes (other than sandals) that are comfortable to wear without socks or stockings. Very very few. That's why they make those nylon minisocks that cover only the part of your foot that goes inside the shoe.
Foot Petals (googlable) are also nice for shoes that rub. They're little pads that you can stick inside your shoes.
In addition, one of the reasons I hate peeptoe shoes like burning is that aside from the fact that I don't really want to see most people's toes and don't find it sexy at all, wearing them is awful because the heel tends to force your whole foot down and into the toe opening. If you like those, which is a total matter of taste, they should probably not be Work Shoes.
I've heard good things about mineral makeup and plan to try it soon. I hope it works.
Getting a manicure will put an end to the nail biting, although if you get fake nails you have to have the salon trim them and fill in the bottom as they grow. Fake nails are, well, fake, and I only had them once because I didn't feel they were clean enough for hospital work, plus they were hard to type with, but my real nails are short because they split easily into layers and then tear, so if I want to have them long at all they have to be fake. However I'm told that the advantage of fake nails for kink is that the edges are smooth, so you can scratch without drawing blood, and if you put your fingers inside someone else's body the nail edges will be smooth not jagged, meaning they will tear neither your latex/vinyl gloves (if desired) nor your partner's innards. If I was dating someone who was into nails I'd get short fake ones and keep them short with fairly frequent salon visits because my own won't grow that long (srsly, the number of times I have had to trim a nail with office scissors because it split boggles the mind) and are very sharp.