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Help me start wearing dresses

I’m leaving my job to go to grad school and this seems like the perfect time to start dressing how I really want to. I’m 26 and I’ve never really been a girl who wears dresses, but I would like to start. I want dresses to become part of my regular wardrobe and not something I just wear on special occasions. So, I have some questions for those of you who wear dresses regularly.

1. What style of dresses is good for those of us with a larger bust and a belly? So far I like skater dresses, but I’m not really sure what other styles I should try.

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2. What are the best ways to dress up a dress, and dress it down? Are certain styles and materials easier to accomplish this with?

3. What’s the best way to deal with chub rub? Should I buy those thigh bands, or chafing balm?

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4. How do I stop worrying that my butt is showing to everyone??? Whenever I wear dresses that are flowy at the bottom, I feel like my butt is showing.

5. Any other dress wearing advice?

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