Growing out a short hair style can be one of the most frustrating and confidence zapping processes a girl can go through, I once heard that 70% of a girl's confidence comes from her hair. Thus growing out a short hair cut over a period of a year can mean 365 bad hair days. As a hair guru this is one of the most common problems I face and I have to admit I have gone through this process myself, having gone from having a funky short hair cut that everyone loved, to looking like a prison escapee as the months of growing out progressed.
Short hair isn't just the hair style for the few, the funky (although it can be funky if you want it to be). In fact, for most people it's actually a better look than long hair- not because they don't have beautiful long hair, but because a) short hair is quicker and easier to do, so they style it more often, and b) the natural oils in your hair make it all the way to the ends with short hair, so it stays healthier without a lot of time and effort for various treatments.
First, you should consider your face shape when you get your hair cut. If your face is round, you probably don't want to go with a pixie cut or something super-sleek. Instead, try something with choppy layers around your cheekbones and length that falls a little below your chin. Add a little volume at the top and some side-swept bangs and you instantly elongate the appearance your face. On the other hand, if your face is long, you may want to add lots of long bangs and cut your hair chin-length to shorten the appearance of your face. Square faces will want to go with softer layers instead of blunt cuts, while heart-shaped faces look great with styles that flip out and balance the thinness of their face at the jaw.
Once you've determined what hair styles will best compliment your face, talk to a good hairstylist about your lifestyle and what you want out of your hair. If you don't spend much time on your hair, go for something lower maintenance. If you're willing to spend a little more time, you might go with something that will take a little more time. Realize that any short hair style will take less time to style, but may need to BE styled every day, especially if you cut it too short to put in a ponytail. (That's why they invented hats, though, so don't despair.)
For pixie cuts, the easiest way to do them is to dry them most of the way and then add a little gel. Use the gel to pull the hair in any direction you want, and don't worry about getting it smooth or perfect. Go for fun and a little messy.
For straight, short hair, make sure you're using products that will keep your hair smooth and sleek, then dry it straight and finishing the straightening with smoothing products if you need them. You can also add a little pomade and pull your layers out a little to make a messy, choppy look.
If your hair is curly, use a diffuser to create controlled curls, and use products that dry soft and bouncy. No one wants their hair to be crunchy, especially when it's all up around your face and needs to be swinging and fun.
Don't be afraid of short hair. It's stylish, easy to do and healthy for your hair. Better a bob that looks good every day than long, flowing hair that you only let out of its ponytail for special occasions.
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