Hi Alana,
Wanted to mention about toppers.... have you considered Talbots? Their plus size line for jackets and blazers are well made, classic and in the under $160 range. I've stalked some of those jackets through to sale time and have gotten them for as low as $31.00. I've also scored calf hair leopard print and zebra print belts in plus size - excellent quality.
The only downfall is you can only get their plus size lines online - $25 flat rate shipping to Canada. I wear 2X in tops at Penningtons and the 2X jacket at Talbots fits very well.
And I'll echo the transformative powers of the right handbag for an outfit, especially in summer when toppers are out of the question.