First that's talk about boot, flats....Boots can be worn under all kinds of long pants, or over slim-fit or skinny-leg pants, especially jeans. Boots should never be worn with shorts, unless you want to evoke Daisy Duke. Stiletto knee-high boots can be worn with tailored gaucho-style pants, but otherwise only with long pants or skirts. It is always okay to wear flats! Especially ballet flats or canvas flats. Personal, I don't own any of them, because I like to be tall.
If you like flip-flops, canvas flats are a good alternative that are not quite as sloppy-looking (especially if your flip-flops are the plastic and foam kind).
If you are short, but thin, I would stay away from tight tops, skirts, and stilettos, especially if you feel strange wearing them. I would suggest a floaty or A-line knee-length skirt and flats or kitten heels (like stilettos, only with a much lower heel). An A-line skirt will balance out a narrow frame. In fact, you could even go with a gathered skirt to give you hips and more oomph on the bottom.
If you want a curvier figure in your jeans, I’d suggest wearing flares or boot-cut. Something that goes in at the knee will accentuate or give you hips. A slightly higher-waisted pencil skirt with a tucked-in blouse would also be really cute.
My advice is just to experiment with different looks and see what you like on yourself. If all you wear is jeans and flip-flops, you need to expand your horizons!
Hope that helps! That is all I have for you right now. I will be back with more advices. Again....Do not afraid to experiment different things. You never know what you going to discover.
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