I finally found a couple skirts that were appropriate to wear for work. I bought a pair of pantyhose to wear underneath.

I'm not the most dextrous person in the world (to say the least). While putting them on, I accidentally put my finger through one of the legs creating an irreparable run.

Am I doomed to be too clumsy to wear stockings?

I'm hoping it's not a matter of practice, because at US$10.00 a shot, it will get expensive in a hurry.

Is there some way to put them on that even I won't mess up?

Your nails can be quite the problem if they have any rough edges. I never personally figured out how to do it consistently. Perhaps gloves like those used by medical people or food service people would help with that.

To wear a skirt in the winter I bought a pair of black leggings and a couple pair of knee hign socks.  I got them after my sister in law made the suggestion.  They're a lot heavier and great for cold weather.  Plus, like you panty hose never lasted longer than one day for me.  I wear the leggings with dark ankle socks that I've already had for a while.

If you have your nails filed and remove your rings, you can carefully gather it from the top down to the toes. While gathering, it's best to only use one finger per side. If I am careful, mine last run-free for a long time.

Keep some clear nail polish in your purse for small runs.

They're fragile. It's a matter, as an earlier post said, of gathering all the way down to the toe, putting your foot in and GENTLY using both hands with the thumb and forefinger (forefinger should be bent). You kind of half-pinch the material as you go back and forth on each side, carefully working your way up the side and making sure not to over-stretch. You may want to try tights first as they're a lot more durable for someone who isn't used to the motion but, remember above all... FRAGILE! Take care and assume that you'll tear a run if you use too much force. Also: ditto the comments about nails. If your nails are screwed, you have almost no hope of putting them on without damaging their delicate weave.

If you put your finger through, you're using entirely too much force.

Gotta think de-li-cat-e-ly. File nails smooth (for practice, run a cotton ball to and fro on the edges...if there is any snags, you'll find it. "Rubber" gloves are an option, to.

Don't throw away pairs of stockings just because they have a run...they can be re-used to learn technique.

i agree with what has been said and the video..

I keep clear nail polish in my purse, to touch up small runs.. but I really don't break them that much... I keep my nails flied smooth, When I grew my finger nails, it took time to get use to putting on stockings with long  nails.. I love wearing pantyhose/stockings..

My roommate said, that the clear polish is something school girls use, not really adult woman. so just take note what company you are in.

Just wear thigh highs!! you still have to be careful though

There are special gloves you can use, but you might try cheap surgical gloves.

Please don't laugh, ok, go ahead and laugh.  I have heard that putting them in the freezer first (let'em thaw out, unless you like the thrill!) and that will make em last longer.  Dear Abbey ran a series of letters on the subject once.  Also, $10 is pretty steep for one pair, unless you like designer.  Try onehainesplace.com  they have multipacks at $4-$6/pair.  I happen to love silk reflections.

Thanks for the great responses.

Joules, that video was super helpful. (Though the lady's expressions and movements were so steamy I almost had to take a cold shower. There goes my fantasies of being straight...)

Kathyk, I do own a pair of leggings, but stockings seem more appropriate for work. And something about the way stockings feel on my legs. Leggings just don't feel the same.

Just roll them, put them on like two bundled socks, then slowly pull them up.

Oh yeah, and get something thicker. The thinner, the more fragile. Besides, for cold weather, thin stuff is just plain useless.

Its part of why I never liked them really. They lasted a few days at max for me if I used them, in the thin ones I felt a bit cold but at the same time sweaty. And they just were too fragile. Maybe good for delicate people who really are very gentle to their clothes and then do only stuff that is gentle as well. For me, I always managed to nick them somewhere - the closing door of a subway, the suitcase of some person in the train, my own shoes if I walked too much and they rubbed slightly, a table or chair standing in the way a bit, fingernails, toenails,... there are more expensive ones that can stand a bit more of a beating, they usually are warmer and thicker as well. i still managed to destroy them. So really I am not a big fan of them anymore.

gathering at the toes and a lightness of touch is about all that helps, i think. that and practice of course.

the other side of my thoughts on the subject is; who doesn't love a good edgy run sometimes though? tease that thing out, get a couple of ladders in there, the world loves a punk

The answer to your question is: You are not too clumsy for stockings, you are just inexperienced.

First and foremost
      You must learn not to "grab a handful", keep your fingers straight and thumb parallel to the fingers.

Follow the good advice on the nails.
If your hands are near female norms, a pair of cotton lingerie gloves really helps reduce nail snags.

An inexpensive pair of white cotton gloves is a good alternative.  Look for Disposable White Cotton Gloves, Cotton Glove liners, Cotton inspection gloves, etc.

It takes practice and care.
Find the correct size for you, buy a discount multi-pack of low cost stockings.

While imagining they are $20 a pair and they are your favorite ones, gently roll them on.
Practice, practice, practice

Soon you be so good at putting them on, that you will worry about removing them safely 

Then buy better pairs.
     Skip the extra sheer and go for the everyday or "energizing" ones that are stronger.

.... I still carry a spare pair in my purse, in case of unexpected fashion malfunction after using the restroom

-Cindi