It's multifaceted. There are so many kinds of judgements.
An actress having lots of sexual partners (a la Marlene Dietrich) can be seen as irresistible, alluring, a femme fatale.
A less famous woman can also be seen as foolish as so many women are murdered. If you are going home with multiple random men, you could run that risk.
For Mata Hari. it was fatal and having multiple lovers (one French and one German, during WWI cost her, her life... in front of the firing squad).
A lesbian with many many women partners, like Jo Carstairs (The Queen of Whale Cay), was seen as rather dashing... then again would she have bedded so many women and some of the best looking ones too if she hadn't been a rich oil heiress? Probably not.
History shows that if you have money (and fame) life can be a conveyor belt of sex as there will always be a ready never-ending supply of partners; Madonna, Mick Jagger; Pablo Picasso; Barbara Hutton; Peggy Guggenheim, Leo Di Caprio, etc are pretty good examples of this...
Interestingly enough, in the first publish diaries of Anais Nin, the general picture is one of this adventurous creative bohemian woman exploring life and experiencing numerous love affairs because she was so brilliant and alluring - a woman that men were clamouring to be with her. She is their muse. She is their everything.
Since then we have learnt more of the actual reality instead of Anais' version of reality. Sadly a lot of her great love affairs where with men, who to use a MN term, were Cocklodgers, as Anais (or more precisely, Hugo, her cuckold husband) was footing the bill. So the Houseboat on the Seine, which you are renting and have moved in your penniless lover, looks a lot less romantic and attractive after a while... I imagine. Still it's a pretty fantasy.