I'm with you....I look horrible with my hair up because I have a long face with a pointy chin and ENORMOUS ears. Kids teased me and called me "Dumbo" when I was a kid (after a cartoon elephant for those who are too young to remember!). But sometimes when I work out I really like to put it in a ponytail. The only thing that makes me look not so hideous is if I kind of pull the hair forward after I put the elastic in, so that it is fuller behind my ears instead of really flat and slicked back. I don't really know how to explain it any better than that, but it really gives the ponytail a whole different look. I also like for my hair to be not so smooth when I put it back in a ponytail, and to have kind of a rougher texture, so I kind of lift pieces and spray them with hairspray, and then let it dry before I put it in a ponytail. Hope this helps!
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Cheryl