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Most of the people who come up with ideas for fashionable hairstyles don't stop to take eyeglasses into account. As a result, eyeglasses have a nasty way of interfering with the look of many hairdos, crowding out the face and distracting attention from the awesome stuff your hair is doing. If you have no choice but to wear glasses, or even if you just wear them because you like the look, try on a few hairstyles that not only don't clash with your glasses, they look downright fabulous alongside them.
Rules of Thumb
Generally speaking, there are two kinds of hairstyles that look good with glasses; styles that leave your face as clear and uncovered as possible, and "big hair" styles that sweep over the glasses and minimize the appearance of the glasses. What you don't want is for your hair and your glasses to be competing for space on your face, crowding your features. In addition, the shape of the hair on your head needs to complement the shape of the glasses on your face, but in this case, competition is a good thing; combinations like big hair, small glasses or big glasses, small hair, will look unbalanced.
If you're looking to get a short haircut, take care to avoid a cut that looks too tight and tidy and encroaches on your face. Short, tidy bangs that cover your forehead and run straight across can easily compete with your glasses for space on your face. Another common pitfall with short hair is sideburn patches; sure, they're cute, but your glasses earpieces will disrupt them heavily. If it's too late to reconsider your choice of haircut with your glasses, wear those sideburns tucked behind your ear and use some product to sweep those bangs up and off your face, giving your hair some volume in the process.
Long and Medium Hair
With long and medium hair lengths, volume is almost always a good thing. So are waves. Even if you're wearing your hair tied up, you want that ponytail or bun to be visible. As with short hair, the best look for bangs is long and swept to the side or swept off the face while the hair is worn down. Avoid super-tidy hairstyles, like straight bobs with neat bangs; these styles are meant to frame the face, but they're not designed with glasses in mind.
Different styles and sizes of glasses frames look better with different hairstyles than others. In general, large frames need high-volume hair to balance them out while smaller frames look better with less volume -- though you'll still want some to create visual interest because even small frames can overwhelm the face without this. If you have wide frames, try to create hair volume on the top of your head to balance them out, but avoid volume that extends from side to side, as too much horizontal shape will enhance the wide appearance of the glasses.