Jess looks mature, sleek and über-blond in her all-black blazer, slim-fit legging and suede bootie combo.
Sparkling in this long-sleeve silver sequin mini with blinged-out earrings, Jess could steel the show at younger sister Ashlee Simpson-Wentz's premiere of Chicago.
Jess shows her class and sass in this tank-style black mini with cinched waist and sparkling peep-toe pumps.
If there was ever a way to make an androgynous vest suit sexy and fem, Jess does it at Operation Smile's 8th Annual Gala.
Looking busty and all-American in this red and black striped number with tan wedges and gold Chanel hoops, we can't blame our servicemen for being a tad distracted.