Fashion & Beauty
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I have always been terrible with makeup. Whenever I put it on, it looks all cakey and I end up rubbing it off because I have a nervous habit of touching my face. I want to start wearing a little bit of makeup to get a natural, carefree look when I go out and minimal enough that I can go to work (1st grade teacher at a Catholic school) without looking like a Jezebel.
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Re: Makeup without makeup
In that case, I would go with a tinted moisturizer. It's more forgiving than foundation, but it still evens out your skin tone and helps you look more polished. I'm a big fan of NARS tinted moisturizer. It's pricey, but a little goes a long way,
If you don't want to bother with a bunch of eye make-up, using a curler and a mascara will help brighten/open up your eyes. Dior Show is amazing, but seriously, Maybeline Great Lash is nearly as good and it only costs $5.
For some color, I love me some blush and bronzer. An easier approach may be a cream-to-powder stick, like The Multiple, also from NARS. It's very blendable (just using your fingertips - no need for brushes), and you can layer it on as light or as dark as you want. Also, you can use it on your eyes or even on your lips with some chapstick or gloss on top.
Some people suggest Sephora so that you can sample makeup from various brands in one location. Personally, I like department stores. You can call ahead and find out about any promos they are doing. Also, many give a free makeup session if you buy $60 worth of makeup.
Good luck!
I don't think that's going to happen--you are GORGEOUS in your siggy pic. But I second tinted moisturizer as a good start--and most have sun protection.