High-top Converse sneakers, also known colloquially as "Chucks," work well with shorts, leggings, cropped pants, jeans and even skirts and tutus. Converse introduced its high-top Chuck Taylor basketball shoes in multiple colors in the 1960s, and they have become a fashion classic worn casually by many celebrities.
Wear Chucks with a pair of shorts and a chunky sweater and socks barely peeking out for a casual style. Adding a pair of tights rather than socks when wearing shorts creates a fashion-forward look. Pairing shorts and high-tops with the right T-shirt and a leather jacket makes for a sexy, casual look.
Try high-top Converse with skinny jeans or leggings with the shoes' tongues pulled out and the lacing stopped at the ankle. Choosing a contrasting color of leggings with this look makes the shoes stand out.
Chucks bring a casual tone to cropped pants and a structured jacket; this look is appropriate for less formal workplaces. With a more casual jacket, high-top Converse and cropped pants are perfect for running errands.
When worn with skirts, high-top Converse sneakers keep a look from feeling ultra-feminine. Layered skirts or tutus worn with Chucks make a definite fashion statement because of the extreme contrast of style involved. With long skirts, high-tops send a grunge vibe that keeps an outfit from feeling too ethereal.