How to Wear Jeans Find the most flattering jeans for you based on your figure. Choose skinny jeans for a sophisticated look with a subtle edge or opt for ripped jeans for a statement-making style. For an on-trend look, pair 90’s mom jeans with contemporary pieces or go all vintage with flares and other 70s styles. To create the appearance of longer legs and an hourglass frame, choose skinny high-waisted jeans and pair them with heels, a tucked-in shirt, and a long coat. Choose between stilettos and ballet flats for a dressed up or casual jeans look, or opt for on-trend footwear styles like sneakers, over-the-knee boots, velvet booties, and small block heels. Finish off your jeans outfit by adding some simple yet stylish accessories.