Hello World!! Now exciting news its Boot Season!! And living in the North, I love boot season. Last year ankle booties came into style, which they are so cute and I love them but as a short person did not think they worked for me. They tend to cut your leg and make you look shorter. I decided to figure out ways to make them work for me.
Jeans- Typically when I wear them with jeans I will cuff my jeans up so that there is a little bit of skin showing in between the top of the boot and the bottom of my leg. I will also typically wear a top that I can tuck in front (or a crop top). This works because it allows for your entire leg to be exposed in the skinny jean and tucking the shirt will bring your waist higher thus making your legs look as long as possible. This is also the way that I typically wear ankles boots so I have the most examples of this.
Casually/ Business casual
Going out with friends
Shorts- Shorts are much easier because once you pair them with heels of any kind your legs are out there and look longer. So I will only wear my heeled ankle boots with shorts, if you wear flat ones it gives off a country vibe. As with the jeans I will tuck the top into the shorts. I love this look for going out in the transition period from summer to fall.
I would also suggest a boot in a color that is closer to your skin tone. This will minimize the color change from your leg to the boot and will cut up the leg less.
Dresses- I have not worn them with boots as much as the others but this is an outfit I love and will wear again. I think it works due to the waist of the dress hitting my natural waist and the dress is semi tight from there down. This high lights my figure and gives the appearance of being taller then I am, even when combined with the booties. I am all about looking as tall as possible.
Let me know if you have any questions.