Dresses: I don't get it!

Driving to and from the tip today I had the windows and sunroof open, sunglasses on, Charles was in shorts and a tshirt and looking at him in the back seat he looked so relaxed yet really hot.
I noticed a car stopped on the side of the road with people talking near it, they'd obviously been out for the day. The women all had lovely summery dresses on, above the knee. I immediately thought of how great they all looked and how lovely it was to see people dressed in summer clothes...pretty dresses, legs out, flip flops on...except then the jealousy set in.

I've never really been able to wear dresses. My body shape seems to not suit dresses. I have a short body and long legs. My waist it quite high up and most dresses which have a waist just don't sit on me properly. I can only really wear empire line dresses but like Heather at SAHMlovingit blogged about today, I end up looking pregnant. Except now I have decided to just not care about that.
My mum is lovely and really honest with clothes. Although as she now says, should I, a 25 year old, be taking fashion advice from her, a 53 year old. At times I don't but most of the time I do. She can tell me if I look big or if I look pregnant.

When I was pregnant with Charles I took full advantage of the fact that I could wear empire line dresses. I loved it, wearing dresses completely changed how I felt about myself. I felt pretty, I felt attractive. Although most of the time I did wear the dresses with leggings.
The reason I will always wear leggings with a dress, or tights, is because I just don't get the fact that if a gust of wind comes EVERYTHING is on show?! Is it just a case of wearing big knickers? If that is the case then ok I can deal with that. Although, why am I the only one who seems to not feel that comfortable with the fact that my dress could blow up and reveal my underwear??! Or is it ok???
Maxi dresses are of course an option.....but running after a toddler + maxi dress = injury!!

10 years ago I had amazing legs [I will have to scan a photo for my Flashback Friday post soon my mum has of me and her framed so I can show you] yet now they are quite chunky and my thighs meet at the top. Although I see a lot worse than my legs, a lot lot lot worse, I can help but feel like I NEED to cover up.
Water retention in this pregnancy has resulted in stretchmarks on my left calf :-(

I think what worries me the most is what other people think. How horrid is it that we spend the majority of our lives worrying about what other people think of us?? People can be so bitchy too, why should I have to cover up my legs just because of some stretchmarks. Its not  even like they are THAT bad, and someone would have to really be looking to notice them, but still I know they are there and know how some girls will just look at other girls finding faults.

As I said, I can't be bothered to worry too much about whether or not I look pregnant in a dress. As long as its clear that its because of the shape of the dress and not the tummy within it.
Except I have no idea what to do re: legs, or most importantly.....bum flashing!
Or do I continue life in dresses and leggings or hazardous maxi dresses??