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A round face shape is cute and cherub-like, but it can make you look like you have a lot of extra weight on you -- that's something no girl wants. It's OK, though, because with your layered, medium-length hair, you have lots of different ways to style your hair to elongate your face, making it appear thinner and more proportionate overall.
To elongate a round face, build up a lot of volume around the top section of your hair. This draws the attention up top, elongating your face rather than making it look wider and fuller. This style works best on short to medium-length hair. Blend a bit of hair pomade up between your hands and run your hands through your hair. Don't worry about getting it "perfect" -- you're going for an effortless, roughed-up look. Pull up hair in random sections and smooth the very front section of hair down and off to one side.
A chic sideswept style does a lot more than make you look sultry and flirty -- as if that weren't already enough. It also creates an elongating angle on your face, slimming it as a result. When you're blow-drying your hair, style it over to one side -- including your bangs if you have any. Use a bit of a flexible-hold hairspray to keep it in place. Sideswept bangs and layered fringe create a flattering arc on your face, taking the attention away from the width of your face and elongating its appearance instead.
You have a fair amount of hair -- at medium-length it hits around shoulder-level -- and adding a few skinny braids randomly around your head is going to draw the eye downward, following the lines of the braids. This creates a slimming, elongating effect on your face -- just what you want. Braid 1-inch-wide sections -- a few near the front and some at the back -- and secure the ends of each section with a small, clear elastic.
A hair pouf style focuses the volume on top of your head, making it a really ideal style to elongate your round face. Pull up a section of hair on top of your head, from temple to temple. Tease over this hair at the roots to build up some volume. When you have some height in your hair, hold the section together and rake your fingers over the top gently to smooth it out a bit. Push the section forward slightly to enhance the pouf and pin it in place.
With your medium-length hair, styling your hair in a low side braid creates a really long line, making your face look longer and slimmer. Try a fishtail braid for something different. Part your hair far off to one side, slick your hair down with a bit of styling gel and pull it together into a low side ponytail. Divide the hair into two even sections. Cross a strip of hair that's about 1/8-inch wide from the outside of the left section over to the inside of the right. Move a section of the same size from the outside of the right section to the inside of the left. Continue braiding down the hair this way and secure the ends with an elastic.