Here are the 5 hottest Hugh Hefner girlfriends. Many of Hef’s girlfriends look quite a bit a like, but some stand out and the crème rises to the top! From the girl-next-door, to the brunette stunner, to the law school grad, to the one put a ring on, Hef’s babes have been impressive to say the least! They’re all special in their own way, but it takes a special girl to be one of the hottest Hugh Hefner girlfriends!
- Holly Madison. One of the "Girls Next Door" on Bravo’s popular series, Holly Madison was Hef's girlfriend for seven years and the number one girl in Hef’s life for six of them. One of Hef’s most ambitious ladies, Holly produced "Playboy" pictorials in the last several years of her relationship with Hef and began carving out a career for herself. Holly’s girl-next-door personality, ambition and devotion to Hef make her one of the hottest Hugh Hefner girlfriends.
- Barbi Benton. As Hugh Hefner’s first girlfriend, Barbi makes the list as one of the hottest Hugh Hefner girlfriends. Known as one of the quintessential "Playboy" models, Barbi is in the minority of girlfriends as being one of the only brunettes in the bunch.
- Brande Roderick. Both a "Baywatch" babe and a "Playboy" centerfold, Brande’s list of credentials lands her as one of the hottest Hugh Hefner girlfriends. Brande’s signature blonde locks, sparkly baby blues and sweet disposition make her a classic Hefner lady.
- Kimberly Conrad. No one can argue this lady’s pedigree from Playmate to Playmate of the Year to girlfriend to wife in a year and a half flat! It’s Kimberly’s determination, as well as her all-American good looks, that make her one of the hottest Hugh Hefner girlfriends.
- Izabella St. James. This is no dumb blonde here. As a law school grad, Izabella is not only one of the hottest Hugh Hefner girlfriends, she’s also one of the brainiest!
What Others Are Reading Right Now.
6 Signs She Wants You to Come Talk to Her at the Bar
These not-so-subtle hints mean legit interest—and time for action.
10 Types of Tattoos Women Love
That dumb bet you lost in college? It’s actually endearing.
How to Turn (Almost) Every Lady’s Head
Top female stylists share their favorite men’s looks.