Many women in today's fashion world completely avoid wearing stockings which I think is actually okay for certain occasions. However there are still those events and times when wearing nylons is definitely appropriate, even expected, and you need to know how to choose the right ones. Wearing the wrong kind of nylons could result in fashion disaster and having the perfect ones could swing the pendulum to the other direction of a fashion bulls eye.
One of the things to always remember is that your stockings should match your shoe and that your shoe should never be lighter than your stocking—ew. Probably nine times out of ten you can get away with a nude sheer stocking; that particular shade goes with just about anything and can give your legs a nice smooth look. Depending on the occasion, you could want other kinds of nylons. There are stockings that are more shimmery for parties or nighttime events, black ones for concerts or particularly fancy affairs, and there's even super sheer for a look that really just evens out your legs without looking like you have stockings on at all.
One of the issues with women and fashion today is persuading women to actually wear nylons. Many had unfortunate experiences with stockings in their youth and as a result refuse to ever wear them. The key however is in finding a good quality pair of nylons. Not all nylons have to be itchy, riding up, or falling down; I've had some amazing pair where I hardly know they're there when I'm wearing them. Remember though, that in finding a good pair of nylons, it probably won't be totally inexpensive; sometimes investing in a great pair of nylons is a most excellent investment for your wardrobe.
One of the perks of nylons is that, not unlike foundation for makeup, they "tone" your legs. Not meaning they make your legs look muscularly toned, but they visibly even out the surface, smoothing out imperfections and many discolorations. One of the important things to remember though with nylons is that you need to shave your legs before wearing them, otherwise you'll have unattractive hair poking out of your stockings!
Know what size you wear and always check the sizing on the particular pair you're looking at to make sure you really are buying the right size for that particular brand. If you buy the right size in a quality brand, you shouldn't have any problems finding the right stockings for you. Nylons don't have to be uncomfortable and unbearable—wear them to highlight your legs and give you a extra boost of confidence!