Who would look good as a woman?

Young Leonardo DiCaprio- he even had the hips

The Biebs, of course

Hillary Clinton

[quote] The Biebs, of course

With those awful tattoos?

Candis looks good

[quote]Who would look good presenting as a woman?

Fixed

Well hello!

R7, Franco looks disgusting and dirty even as a woman.

Jude Law was stunning in drag in Sally Potters film.

Jason chaffetz is an ugly guy, but as a woman, he doesn't look half bad....

My eyes! My eyes!

None of them. You can always tell. Even the lady boys from Thailand can't hide it, and they're the best you can get.

R12 = Jeremy Renner

James Marsden

The best, R13. Remember that. Forget I said that.

Timothée Chalamet makes a stunning woman based on these photos put through the FaceApp

Been there. Done that.

Miles Heizer and Paul Dano.

John Goodman.

John Goodman

None will look quite as good as me.

You rang, OP?

Ken Burns

Ewwwwww, R23.

Rudy Giuliani

Who's that at r22?

Miss Cillian Murphy, R26.

Thanks r27. Wow, he looks so twinkish in his that pic

Miss Cillian Murphy should transition. She doesn't look hot at all as "drag king."

Trey Gowdy - looks like a raging cunt. I don't know about attractive.

Brenton Thwaites - he's so pretty.

Barron Trump - looks androgynous, pouty lipped tranz somewhere on the spectrum. He's special..(needs)

[quote] Brenton Thwaites - he's so pretty.

He looks too manly.

Dave Foley always looked great as a woman.

Oh please, got this. ME!

Mitch McConnell has the face of a kindly old grandmother.

Trump. All of them. Let's cut their dicks off now and get their balls rolling.

[quote] Mitch McConnell has the face of a kindly old grandmother.

He has the face of a turtle.

You, OP, you would look good as a woman. I can tell.

Tom Holland

Jared Leto

Melania has potential, with the right work undone.

Please don't mention me.

Rob Lowe

Tommy Haas, the over-the-hill tennis player. (Rumor has it he's a crossdresser.)

Chris Pine

No one can compete with Cillian Murphy, so they shouldn't even try.

Gael Garcia Bernal

Milo Yiannopoulos, or at least he'd look better as a woman

Mmmmmm tell me more

I used to think this guy did, but it's only the coyness and flirtation of the eyes. The nose is too prominent, and the inverted triangle of the high, defined cheekbones and pointed chin make the face clownish, which it's really meant to be rather than feminine.

Trevor Donovan was born to be a woman.

I am dude and I don't even look good as a dude, but I would make one God awful looking woman.

It wouldn't take much, r47. He already looks like Alice Ghostley.

Joan Crawford

Ben Barnes

David Muir

Rob Lowe

James Marsden

Matt Dillon

Jared Kushner

Guy Pearcce

I present for your inspection, Miss Mitch McConnell.

James Bradley

[quote] James Bradley

Why him? He has a very masculine face.

Michael Pitt

Josh Hartnett

Lucas Till (MacGyver)

None of them. Even LaVerne Cox still looks like a drag queen.

Good choice, R66. Pity about his neck mole.

Lucas Till almost looks like a woman without any makeup.

I don't know that it's good, but our president does look like an actual woman. His mother.

Anyone that "Female" looking app? Want to run Lucas Till through it?

Dave Foley is the winner:

....

[quote]Which guys would look good and natural as a woman?

Define "woman", OP.

Looking like a "woman" a straight guy would want to fck.

Mike Vogel would make a beautiful woman.

I can see that, R76.

Billy Crudup made a pretty girl.

Jude Law

Ian Somerhalder. He's quite pretty in person, hence the scruff and the squint in more recent photos. This is an older one:

It's the jaw & the adams apple that gives away. Any pretty male actor who doesn't have a very strong jawline like Jared Leto, Eddie Redmayne, Jude law, Timothy Chalamet, the guy that Sam Smith is dating, Tom Holland....there are so many would make a pretty woman.

Johnny Depp

Despite the leathery appearance and bad wigs, Melania pulls off a woman... more or less.

the Senatrice!

Rafael Nadal

A young Pierce Brosnan

Ugh 🚨autogynophile circle jerk alert! 🚨

Anyway it’s not the jaw that’s the “giveaway”, there’s plenty of gals with big jaws (that tranny looking bitch who speaks for the president) and some have prominent adams apple (Maddow). No the ultimate tell is the brow riidge and how deep set the eyes are, along with how Jorge the eyes are relative to face (women have dramatically smaller faces/heads).

Jorge???? I meant LARGE

Jonathan Groff

Stephen Amell -- perfect heart-shaped face and full lips.

Matthew Gray Gubler -- even has the body-type of a female fashion model.

John Schneider

Maybe John Schneider YOUNG?

Thomas Gibson

Ben Hardy

Does Ben Hardy appeal to any DL trolls?

Steve Kornacki

Congressman Eric Swalwell would look beautiful as a congresswoman.

No he wouldn't, R98. He has a block face.

Stephen Colbert

Michael Fassbender

Matt Dallas

Fassbender has no lips and a skull like a cinder block; would NOT look good as a woman.

Jonathan Bennett

Colton Haynes

Merlyn Wood from Brockhampton

****

Straight too (but gay friendly ) from what I can glean

The Triage Guy

Should be "The TRIVAGO Guy"

Ernest Borgnine

Stephen Colbert

Bruno Mars

R113 Omg he really does! Always wondered why his face always seemed “off” to me

Teddy Geiger Obviously he/she thinks so.

Scott Disick

Gavin Newsom

Luke Norris -- "Dr. Dwight Enys" on Poldark

Tom Cruise

Do old dykes count as “women”...if so: Clay Aiken (owns this thread)

Max Theriot from Bates Motel

Lee Pace. His neck is too thick, but it's still pretty convincing.

Dylan Strawberry

Harvey Weinstein

Sebastian Stan

Luke MacFarlane

James Wolk -- Beautiful big eyes and lush full lips.

Jenny Thunder

[R. 128] Who is Jenny Thunder? She looks familiar. TIA.

Donald Trump

Really?

Leonardo was surprisingly good in the lead role of THE JUDY ZiPPER STORY (1998).

Jensen Ackles, R129.

Jensen Ackles -- next to Miss Cillian Murphy -- owns this thread.

A young Roger Taylor from Queen

Lil Peep

....

Daniel Radcliffe

Rain Bi, Korean Pop singer

Ron Perlman

A young Peter Capaldi

....

Andreja Pejic

Here's a picture of Andreja Pejic on the right before gender reassignment.

Here's another picture of Andreja Pejic when she was a man.

Andreja Pejic, a transgender, who used to be a man, was originally hired as a male model. Because of her too girly face, designers started putting her in women's clothes.

Noel Fielding, a British comedian

Katy Perry would be very pretty as a woman. Maybe some day we'll see that.

Chandler Massey

John Chandler (WNBC New York)

Jeremy Peters MSNBC Gorgeous with a long swan-like neck.

R149, Chandler may be cute but he doesn’t look like a woman.

Michael Jackson in the early 90s.

Eric Bana

R59 ...Good one!

Taylor Hanson

Douglas Booth

Matt Barr -- a blond guy becomes a blonde beauty

Peter Jennings In fact, he was a crossdresser (convincing one) under the drag name, "Jennifer Peters."

Alex James, from Blur(in a video clip but I can't recall which song it was) and Johnny Depp passed pretty well, I think, in an episode of Jump Street.

Young East Asian male ‘idols’ (popular tv actors/musical stars/magazine models) can look utterly convincing as pretty girls.

Subtle crossdressing is also considered as an innocuous pastime over there, especially in Japan. A young Japanese man dressing as a girl has ‘cute’ or ‘sweet’ & wholesome connotations totally opposite to the expectations Westerners have. Perhaps it’s easier to do in certain Asian societies where the rigid social mores clearly define a limited female role of passivity.

For an example, actor Shogo Suzuki can pass (the first ‘girl’ in the clip below).

R157 I would love to see that, I covet a cute andro blond and Matt looks pretty as sin clean-shaven & with longer hair.

Sadly though, I fear the window has closed on him passing as a cute young woman because he has gotten too muscular & wiry and his face has naturally aged too much. Wonder if he’d look as a more mature gal?

Many male models would look good as women such as Mark Vanderloo. Perfect lush full lips.

Creepy tranny chasers ITT

Charlie Heaton

150 replies deep and no-one said Cole Sprouse yet. You all feeling alright?

And Dylan would make the prettier wench.

Greg Kinnear

[R. 165] Wow! The twin Spouse "SISTERS."

Why do gay men dress up as women? Why do drag queens look so ugly? Is it because of cunt envy?

R168, it’s because their mothers were all maids.

Most of the men on this thread look very pretty as women. In fact, a few even look better as women than as men!

R45 strange that Kitty of ‘Breakfast on Pluto’ looks just like Grace Burgess (played by Annabelle Wallis), who was the main female love-interest to Cillian’s character Tommy Shelby in ‘Peaky Blinders’...

R171, Miss Cillian was prettier.

Oh, don't mind me you cunts!

Tony Curtis in Some Like It Hot

Jared Leto. Michael Pitt.

When younger, Damon Albarn would have made a pretty Winona-esque gamine.

Now he’s in his late-40’s, husky & grizzled, not so much. Same goes for Alex James.

[quote] Oh, don't mind me you cunts!

What’s that?

When younger, Lyle Wagoner, from The Carold Burnett Show, would have been much prettier than Carol.

Anyone would have been prettier than Carol.

Froy Gutierrez

Timothée looks like a young Camille Paglia but feminine

Toby Regbo

Adam Scott (golfer)

Billy Bush

Tyler Breeze is pretty cute like a girl, facially.

Colton Haynes-if he took drag seriously (the eyebrows gotta go) - would make a beautiful woman. He has the same basic bone structure/features as Angelina Jolie.

Vince Neil.

Josh Henderson

[quote] Josh Henderson

Why him?

Heart-shaed face, full lush lips and small jaw.

Thanks, R190.

Arnie Hammer

R192 He's ugly

Eddie Redmayne

Johnathan Taylor Thomas

Michael Jackson

Bon Jovi

Jon Bon Jovi and Richie Sambora

Simon Le Bon

Bruce Jenner

I’m too tall, 6’2”.

Mick Jagger

R201 No problem I'm 6' 2¾"

Steven Tyler and Mick Jagger

David Bowie

[quote] Michael Jackson

Not any more.

Robert Sean Leonard

Young Robin Zander from Cheap Trick

Orlando Bloom

Bret McKenzie, actor/comedian

Finn Wolfhard. I guess more girl than woman.

Young David Sylvian, English singer/musician

Roy Moore

A young Alec Baldwin -- blue eyes, small jaw and lush-full lips.

Ms. Ryan PhiliPAY.

Chaz Bono

Tatum Channing

R194 looks like Carrie Brownstein.

R217 forgot to post

Troye Sivan in drag at 2:31

A young Robert Redford

No, just no, R221.

Pitt

DiCaprio

Colton...

Angelina Jolie and Jennifer Maniston

Brad Pitt

Leonardo DiCaprio!

Chris Pine

Gael Garcia Bernal

George Clooney

Johnny Depp

Benedict Cumberbatch

Patrick Swayze

All from R224 to R233 make damn ugly-looking women except Brad Pitt. He looks more beautiful than most women in the pic at R226.

Carter Oosterhouse

Thor

Carter Oosterhouse is a real name? WTF!

Carter Oosterhouse's real name is Ezra Cohen.

Alexander Dreymon

Garrett Clayton would make a beautiful woman. In fact, he was born into the wrong sex.

Why do you say that, R240?

Jared Leto

Kate Winslet

R239 Dreymon would make a great drag queen or transverstite, but his jaw is too square. Beautiful eyes and mouth though

David Duchovny

James Norton

Jeffrey Donovan

1990s Liam Gallagher. [Yes, even with his eyebrow.]

Sam Heughan

Steven Pasquale

Steven Pasquale's bad nose job really makes him look effeminate. It's a good start to becoming a beautiful woman.

President Trump

Because he is THE BEST at everything he does and so if he wanted to be a woman he'd make a GREAT woman. Probably the BEST WOMAN EVER.

He'd Make Women Great Again, he would!

Billy Crudup

Elvis Presley

Santa. (A jolly fat woman.)

Garrett Hedlund

David Tennant.

Ryan Gosling Same shaped face as David Tennant

David Tennant is way more cute than Gosling.

Paul McCartney

Dan Stevens "Matthew Crawley" Downton Abbey

Gosling is ugly

Jon Bon Jovi looks super femme here, pretty even.

Gossling is fug.

The gif at R263 is very feminine.

Michael Vartan

John Travolta

Rudy Giuliani

Matt Lauer

Lauer is so unbelievably gross. Ick!!!

Lauer is gross in MANY ways!

Ryan Seacrest

Charlie Hunnam

Freddie Highmore

Jeff Ward. First saw him on SyFy, Channel Zero:The No-End house which was pretty good; he's also on Agents of Shield. Very pretty eyes and face.

P. Allen Smith -- the gardener

Eddie Redmayne

James McAvoy

Simon Baker

Mangelina

Dylan Sprayberry

Gavin Newsom

Bobby Flay

Chris Evans

[R 283] I don't recognize the beauty. Who is she?

R285 Hugh Laurie

Peter Scolari

Pat Robertson

.......Judge Judy

When crossdressed, 21y.o. Corey Haim (RIP) looked cute as a button in a sturdy Lilith-Fair lesbian way.

Jim Carrey

James Franco

[post redacted because linking to dailymail.co.uk clearly indicates that the poster is either a troll or an idiot (probably both, honestly.) Our advice is that you just ignore this poster but whatever you do, don't click on any link to this putrid rag.]

Shah Rukh Khan

Peter Gallagher

Just tried the Face App on Peter Gallagher -- he looks just like Jackie O.

(Anyone know how to post a photo?)

Peter Scolari

Keith Urban

Charles Busch

Steve Buscemi

Stephen Dorff

James Franco

David Tennant

Some of these decidedly do not "look good as a woman".

David Tennant plays the Doctor's "gorgeous time traveling assistant.

Max Theriot

Max is beautiful. Excellent choice.

Chelsea Manning

Ken Burns

Michael Woods, BBC Presenter/Host

Neil Patrick Harris

Patrick Dempsey

There used to be rumors on DL that Patrick Dempsey was a cross dresser and that he looked very attractive when so dressed.

^ that was Brad Pitt

Jeff Glor

R315, Brad Pitt dressed in drag for an edition of Rolling Stone. The rumors I read here were about Patrick Dempsey and Adam Scott, a pro golfer.

Rumoer about German tennis pro Tommy Haas being a crossdresser, too.

R315 if memory serves I think that rumor/blind was in fact about James Marsden.

Tom Hanks

Taylor Lautner

Taylor Kitsch

Taylor Swift

Taylor Maydh

Alexander Skarsgard perhaps?

Pretty actor Jordan Brower would make an interesting shy geeky lesbian.

I always thought Jon Bon Jovi looked quite feminine.

Trevor Donovan

Trevor had too much of a square masculine face.

Jeff Glor

Josh Duhamel

James Murray British Actor

Brad Pitt

Jim Morrison of The Doors

Bob Barker when young

No one! Just another attempt by the transgenda Mafia to demasculinize men. No one who was born a man really looks great as a woman. It's the reason why drag queens are used for entertainment... because we're in on the joke. IT'S NOT MEANT TO BE TAKEN SERIOUSLY! Even RuPaul loves living as a man once his drag comes off!

Alexander Skarsgaard

John Leguizamo

The Ground Hog

Owen Campbell

Emanuel Moire, French singer/actor

Ralph Reed

Ryan McPartlin

Phillip McCracken

Hugh Dancy

Travis Fimmel

Matt Barr

Jeremy Brett

Model Jordan Barrett

Good one, R346.

Jason Morgan -- model.

Lulo

John Ritter always looked good in drag

R349 Straight guys consider Lulo to be a trap.

David Hogg

Adam Brody

Ann Coulter

Bobby Flay

Travois Reinking

Dr. Ronny Jackson

a woman

A young Robert Sean Leonard

Jules Horn, male model.

Aidan Turner -- Poldark

Ralph Reed