If These Men Were Women

Starring Leo, Leto and Leno


Have you ever wondered what your favorite actor might look like if he were a woman? What he might wear, what kinds of accessories he might gravitate toward and whether or not he might find himself stricken by the plague of basic bitch-ness.

If the answer is no then I have exactly nothing to show you today.

If, however, your answer is an effusive, “yes, yes, a thousand times yes! I think about how Piers Morgan would wear culottes if he were a woman all the time!,” then I have just the story for you (minus the whole Piers Morgan in culottes thing): a series of illustrated renderings as drawn by Charlotte Fassler of three of our favorite men — Jared Leto, Leonardo DiCaprio and Jay Leno.

Fine, full disclosure, the alliteration was a selling point too.

But right now that is neither here nor there.


Consider Jared Leto in a Givenchy plaid shirt, leather pants by whoever your imagination feels like conjuring and a sheer, knee-length skirt-over-pants plus the Balenciaga motorcycle boots of popular culture-yore — naturally tousled and ombre hair notwithstanding. We thought about putting him in an outfit that might seem more emblematic of his days as Angela Chase’s beau but opted against it which actually proved itself a futile effort because ultimately, when push comes to shove, Jared Leto = Jordan Catalano.


And here’s Leonardo DiCaprio.  Our skillful set of in-house anthropologists determined that if DiCap were a woman, he would likely be Jennifer Aniston. This is precisely why he appears clothed in a banal brown Theory tank top, J Brand jeans and some Chloé sandals which, full disclosure, I own. To maintain to spirit of the male version of DiCap, there are also a pair of Isabel Marant x Oliver Peoples sunglasses to consider and a baseball cap, which Charlotte executively decided to scribe with the letters “L” and “A.”


Finally, here’s Jay. The man, the myth, the chin — who has been known to peel away at the layers of his late night suiting to kick it back more comfortably in a Canadian tuxedo. It’s worth mentioning that he was tux-ing before tux-ing was a thing (or, at very least, before I knew it was a thing). He wears a Saint Laurent belt to show off his pop culture sensibility and meme-brand brogue loafers for the same reason. Not invaluable is the fact that his jeans are by The Row and his fuschia, croc-skin clutch was made specifically for him by Nancy Gonzalez.

Deduction? The man is my accidental style icon.

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  • Hilarious. Although I think Jen Aniston is too much of a sweetheart to be the female version of Leo DiCaprio, the outfits are spot on. I’d wanna be friends with female Jared Leto (maybe just to get his colorist’s phone number)…

    xo, coco | MILLENNIELLE.COM

  • Oliver Lips

    Hahaha Jared is definitively my favorite “fashionista” amongst them!

  • Michelle Glassow Schroll

    Haha! I’m loving this! Especially the Leo one 😀


  • Hahah! You guys are awesome. I’ve actually never wondered this, but I do now! They seem strikingly accurate, too.

    What do you guys think my two (rather different) crushes would wear? They are young Paul Newman and A$VP Rocky…
    (I think Rocky would dress very similarly, actually, as there have been some man-skirts along the way.)

    • Charlotte Fassler

      Looks like we have similar taste Ms. Hager.
      Young Paul Newman- that’s a tough one, I feel like his style was oh so dapper, a bit preppy yet simultaneously rugged and a whole lot of americana. I keep wanting to dress him as a man in modern brands so I will think on this and get back to you.
      A$AP would definitely rock MBMJ Fall 14. Seamless transition.

  • Amazing. First thought: ROTFLMAO. Second thought: Jared Leto’s drawn hair could be my drawn hair. Third thought: I wonder what my dog, Winston, would wear if he were a woman… or human…

  • It makes me sad that Jared Leto has better hair than me. And now he has better clothes too!

  • That’s so cute, you should do more posts like this one! Leo with mini Celine tote looks adorable:)

  • lizzydonald

    going to france in a month- desperately need advice on how to not look like a tacky tourist

    • anna

      be yourself.

  • LexoRexo

    This is awesome. I have days where I wear exactly what I think I would wear if I were a boy – today, is one of those days….tshirt, elbow patched sweater, relaxed jeans, desert boots and an olive green barbour. I look like I am a 12 yr old boy – – but a comfortable one at that.

  • Rebeka Osborne

    Have you guys seen Dallas Buyer’s Club? Jared Leto was an awesome (trans gender) woman in that, albeit not as well dressed as fictional Jared Leto above!

    • Aubrey Green

      Great movie. I’m happy that both Jared and Matthew one the Oscar.

  • Quinn

    I love this post but Nooo. DiCap can’t be Aniston. He’s so bad ass and sexy with a don’t-give-a-shit-how-I-look so Imma wear a grandpa driving cap all the time, smoke some cigs, date some models and Jen is so BORRRRING typical lady celeb, Smart Water spokeswoman.

    • Peroxide B

      I feel like Leo would be more of a Gisele Bündchen…sporty & safe dressing.

  • Aubrey Green

    I love Jared Leto.

  • Amy Sanchez


  • I absolutely love this post, made my day!

  • I wish Jared Leto was my best (girl)friend. (S)he would give me great hair tips!

    Mafalda ❤

  • Kaitlyn

    Ok, this is hilarious! Jared Leto’s outfit is spot on. Female Leonardo would definitely be equivalent to Jennifer Aniston.. everyone’s favorite “girl next door.”

  • kgal1298

    Well Jared Letto has been a woman before in films so that’s really not a hard reach.

  • Haha, love this. You’ve really nailed the female equivalent of their styles, and this is such a fun idea for a post!


  • Namrata

    Haha, the celine on Di Caprio! And Jared Leto is already half way there!


  • Sasha Avgherinos
  • jessie