Here's a tip for feeling okay about your body after you've gained a lot of weight: gain even more weight, like 40 pounds*, then lose it. You feel a lot better about yourself on the way down then you do on the way up. When I first gained weight and got to the size I am now, I was devastated, but I fell into a downward spiral, kept going, and gained a lot more. Then I lost it, and now I'm thrilled to be back to the size I am now, even though I've still got plenty of weight to lose to get back to my goal size, and when I first hit this size, I was furious with myself. It's all a matter of perspective.
And so I wear shorts now, even though my legs are far from svelte and toned. You know what? I just don't care! It's damn hot out, and I don't feel like spending my summer in jeans.
By the way, see the messy ponytail? Gross, right? This is why I chopped my hair off the other day!
*I don't actually recommend this.
Top: Urban Outfitters (similar here)
Earrings: Anthropologie (similar here)
