Hey Cassie,
Try a form fitting midi skirt with pointed toe pumps. These shoes elongate the legs. Also, if you want a looser bottom, pleats are great. I would pair a pleated skirt with a short sleeved cropped blouse and kitten heels or higher heeled stilletos (whichever one you're more comfortable with). Or, if you want to wear flats, wear a pleated skirt, a crew neck white tucked in tee shirt with Oxford shoes. This look would be reminiscent of "Sandy" from the Grease cast, but hey, who's judging? Lol. Try it. As a matter of fact, go all out and add a sporty jacket to the mix! Enjoy