Gotten older, gained weight, killing my confidence

Sarah

I'm 28 years old, so of course I'm not as little as I was when I was 18. I dont look the same as I did in my early 20s. I just wish I was more confident in myself, to be able to wear what I wanted. I want to be able to wear skinny jeans with a tucked in shirt and not feel like everyone is going to judge my weight :( this isn't even the most I've weight. I was 230 this time last year. Since winter hit I've gained 20lbs back from the 230. Seems hard for me to get under 200 the older I get. The first picture is an outfit I consider wearing today... the others are just pictures of myself. Any tips on how to boost my confidence when picking out things to wear?