Stockings -- thigh-highs held up by a garter belt -- differ in structure from their similar counterparts, pantyhose or tights, which are basically one piece, rather than two. Stockings can seem a bit more tricky to wear than pantyhose or tights; but, with a bit of extra care to prevent accidental exposure, you'll be ready to sport your stockings in no time.
Before you put your stockings on, make sure your feet are in prime shape. Smooth foot skin with a pumice stone, file your toenails and slather on some lotion; you don't want jagged nails and rough skin pulling at your stockings and causing a run.
Before you slip on your stockings and garter belt, decide whether you want to wear your panties underneath or on top of your garter belt. Traditionally, panties are worn underneath for a neater look, but this can be cumbersome when it's time to use the restroom. Worn on top, the panties can be slid off more easily in the stall.
Clues On Color
Colorful stockings add a fun, fresh look to your outfit, and they're generally pretty easy to wear. Colored stockings illuminate the leg with a wash of color if they're sheer or a full coat of color if they're opaque. When going for a nude leg look, your stockings should match your leg color as closely as possible; the wrong "nude" shade can look orange or pasty. Also, be wary of white stockings, which make your legs look washed out.
Be mindful of the shoes you wear with stockings. To sport an open-toed shoe, wear toeless stockings. If you're going for the fashionable peep-toe-pump-with-stockings look, that's fine; just make sure no seams are showing through the peep-toe area so it looks accessorized, not accidental. Fishnet stockings outside the boudoir can be risky; go for a nude shade if you're not feeling bold enough for black (or a bolder color).
Before stepping out in your stockings, make sure they don't show underneath your outfit. Bend forward in front of a mirror to see if your garter belt is showing, and sit in a chair to make sure the tops of your thigh-highs don't peek out.