Stilettoscot Thanks for posting pictures of yourself. You definitely have a RURAL/COUNTRY red/white/blue striped theme going on. What I am about to say is just my opinion and you can take it or leave it as you see fit. I think you did a good job color coordinating the shirt and shoes and sensitivity to proper color coordination is a timeless discipline that you want to employ with perpetuity in your newly discovered quest for personal style.
What you can improve? I'd go for a more Urban/Big City look.
The shirt The brightness of the red contrasted with the darkness of the jeans makes you look top heavy. I think you have a high contrast between your facial skin tone and hair color, so I would go with stronger colors like black, navy blue, and dark brown for a color that you want displayed near your face and continues that dark (hair) vs. light (skin) contrast.
Go to a store and hold up many different types of shirts against your face while standing in front of a mirror. Take your time and have fun. For examples on how to combine different tones of dark colors, check out the runway shows of
Raf Simons,
Ann Demeulemeester, and
Rick Owens.
Also, stick with long sleeved oxford button down shirts. If you are hot, you can always cuff up the sleeves, which will produce a relaxed and casual image.
The jeans How low rise are these jeans? How high is the rise, about 9-10 inches? I'm just curious as I can't see from the pictures.
The crease down the front of the jeans adds a vertical stripe, which enhances the illusion of slimness.
I can't tell from the images if they are bootcut or straight cut though. I think straight cut would work for your body type -- provided they cover a couple inches of the heel -- as the straight cut hem will make your legs appear to be one long image as opposed to a chopped/curved image that bootcut or flared jeans will create.
Try some pants as an alternative to jeans. They will dress you "up".
The shoes A bit too loud for my taste. If you want to wear pumps, stick with neutral colored, almond and closed toe pumps: black or brown. The Nine West
Marquee would work well. It's still a pump and the cone heel might better suit your body type. You could also wear them for many years, it would be a timeless addition to your wardrobe.
Good luck and thanks for having the courage to share your progress with everyone.