Over Critical or Fairly Judgmental of My Obesity?

I've spent my entire life critical about my figure, so it's not surprising that when I am actually overweight I tend to obsess over it. That's good in a sense because it kicks me into action. However, I'm embarrassed by what I look like today. Luckily my boyfriend still loves me, but I'd like to one day feel really good about how I look. My 30s seems like the right time to accomplish this. These are my problem areas that I want to work on as I lose weight:

Me @ ~170lbs July 2014

The problem is that even when I weigh less I still have a lot of fat. I won't be happy until I am on the lower end of my healthy weight range - with muscle. What's weird is when I tell others that I need to lose 40lbs-50lbs to be healthy and they look at me with horror in their eyes, like I have some sort of disorder. I have to explain to them that I'm 5'3 and being 115 - 120 pounds is actually healthy for me. I mean, I was shopping this weekend in the L/XL section of a sale rack and a woman literally said to me "you must be shopping for a friend, you are a medium aren't you?" While that's nice, the reality is that I'm on the large side, size 12/14 at the moment. The dress above is an XL. Compare that to 8 years ago when I had lost a ton of weight...

Me @ ~120lbs circa 2006

Clearly I'm a lot thinner here - but you can see that I still have lots of fat. Wearing a size 8 jeans also isn't what I would consider "skinny" so I was still far from what my likely health weight is. I was exercising by riding a bike to and from work 5 times a week and I wasn't eating that much at the time, so that's why I lost a lot of weight in three months without paying attention. It's the only time in my life this happened. I had a good 15 minutes of intense cardio everyday for a month pushing my heavy bike up a giant hill in Berkeley. The outside of my thighs were rocks. But still, I wasn't thin. That's not my natural body type. I'm going to have to fight really hard to get there. If I lose weight in a healthy, stable way, I'm hoping I can make it.

Why? To be healthy. And to be able to rock a bikini on my honeymoon. To have flat abs before I one day have children. Mostly superficial reasons. But it's good to have goals. I want to do this in a healthy way. That's why I'm here. To hold myself accountable for not slipping. To fit those jeans again! To feel more energetic and stay young as I age. That's why I am here.