I used to consider myself a pear, too. As a young woman, I used to carry weight more in my hips and thighs than in my upper body. With my DS, I received the "gift of bosom," and with the decline in estrogen, my weight distributes differently.
I realize now that, structurally speaking, I'm an hourglass, since I have square shoulders to balance a pelvis that is broad -- even when I'm skinny I still seem broader when viewed from the front. In terms of weight distribution, I was a secondary pear and am now a secondary apple.
How does this change the way I dress? Really, I don't dress for body type. I just note the proportions and wardrobe elements that flatter "me" -- giving myself a unique set of "BA body type" rules, and I make trade offs. For example, cuffing my jeans is fab, but it shortens my leg line. I will cuff, but then I choose a little less contrast in the rest of the outfit, but more vertical continuity. Annother example: I keep defining my waist, but find I need a broader belt or more structure in the waistband to make it work. Low rise pants and a knit top too often reveal that my waist is a bit, um, squishy and wider.
I'd encourage you to gather some pics of outfits that seem to flatter you and make you feel terrific and use them to create a few "formulas" for dressing. BTW --- I used to bemoan my booty, but as I've grown older, I realize that curves in the bottom half make me look feminine, and I like that! Also, my hips balance my slighter wider middle now --- and I'm more accepting!
I've always felt like your WIW show a woman who knows how to dress beautifully, and in a way that flatters her form. I think you can afford to trust your instincts!