Sorry to be blunt- but is your DP the king of fashion or something?
What does he like you to wear? A brown paper bag?
Leah- you are gorgeous inside and out.
Confidence is the key- you need to wear what you feel comfortable in and looks nice on you :-)
*steps off soapbox*

Ps my DH often wears tracksuit pants and things and socks- he has no idea.
I was thinking the same thing!! He in himself is a major blow to your confidence. If you have the confidence, you can usually pull anything off

I tend to wear 3/4 pants/shorts in summer as I dont have the greatest legs either but i see they are out of the question. Try even a different cut in 3/4 pants. Crossroads have some lovely cuts Even Katies.

AND yep, skirts do make you look bigger than you already are. I learnt that lesson the hard way. You might have already seen my weightloss album on facebook.... I too thought they "hid" everything. I was so so wrong and it took for me to look back on photos after I had lost almost 50 kgs to realise that.