Category Archives: Men Wearing Womens Clothes

Men wearing womens clothes (dresses, panties, underwear, skirts) such as male celebrity cross-dressers or male models in designer gowns.

Men Wearing Panties and Bras

Men Wearing Panties. What do you think of the photo below? Do you think it’s cool? Or are you creeped-out by the idea of men wearing panties and bras? We here at Famewatcher are live-and-let-live kind of gals so we are cool with guys wearing women’s underwear. If they can rock it, more power to them.

Anyhoo, we found out that the pic is actually an advertising campaign for women’s pads and napkins by a British company called Dr. Whites.

men wearing panties - dr whites man in womans underwear

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Daniel Tosh Shirtless, Underwear, Crossdressing Photos – Is He Gay?

Daniel Tosh Shirtless, Underwear, Crossdressing Photos. Let’s add another dude to our list of men who wear women’s clothes. Famewatchers, say hi to Daniel Tosh stand-up comedian, writer, executive producer and, most importantly, host of the hit TV show Tosh.0 on Comedy Central. Here’s Daniel Tosh rocking a blue dress as the controversial Miss South Carolina Teen USA Caitlin Upton. [Want more celebrity cross-dressers? Go check out Matt Lauer’s Bikini and Dresses.]

daniel tosh is gay crossdresser

Remember Miss South Carolina? Well, we hope this video will remind you of her: Continue reading Daniel Tosh Shirtless, Underwear, Crossdressing Photos – Is He Gay?

Matt Lauer Wearing Women’s Bikini and Dresses: Celebrity Male Crossdresser

Male Celebrity Cross-dresser: Matt Lauer Wearing Women’s Clothes. What do Jimmy Fallon and Matt Lauer have in common? They are both television personalities, they work for the same network (NBC) and, most importantly, they have a thing for wearing women’s clothes. You can Fallon as a cross-dressing enthusiast in an earlier post: Jimmy Fallon Shirtless and Underwear Photos. As for Matt, well, here he is as Pamela Anderson on Baywatch.

matt lauer crossdressing in womens bikini - pamela anderson

The Today Show host as Jennifer Lopez with Al Roker as her/his Puff Daddy aka P. Diddy aka Sean Coombs.

Continue reading Matt Lauer Wearing Women’s Bikini and Dresses: Celebrity Male Crossdresser

Dermot O’Leary Gay? He’s a Straight Cross Dressing Drag Queen

Dermot O’Leary Gay? He’s a Straight Cross Dressing Drag Queen. Is Dermot O’Leary gay? Heh! Of course not. Despite his love for sailor hats, the X Factor presenter is not gay and is very much married to a girl — see Dermot O’Leary-Dee Kopang Wedding. That’s enough proof to tell us Famewatchers that he is as straight as an arrow. What he is though is a man who loves him his woman’s clothes. So we’re guessing it is more than okay if you are going to say that he is a cross-dresser.

dermot o leary gay sailor hat

Let us check out his cross-dressing ways, shall we? Here’s our imaginary Irish boyfriend as Violet Crawley, the Dowager Countess of Grantham (played by Dame Maggie Smith).

Continue reading Dermot O’Leary Gay? He’s a Straight Cross Dressing Drag Queen

Henry Burris Bra Realness: Football Quarterback Wears a Woman’s Bra

Henry Burris Bra Realness: Football Quarterback Wears a Bra. Let’s add Canadian Football League quarterback Henry Burris to our list of men who wear women’s underwear. Why is he wearing a bra? And is that woman his wife?

henry burris bra realness

No the woman isn’t his wife. Let’s have him explain what’s happening in the pics. Via the Montreal Gazzette: “It’s not a big deal. Basically, it was a birthday get-together with friends. The question I have to ask is, where are the rest of the pictures? The girl in the picture, I know her and her boyfriend very well, and my wife’s aware of everything, and I really don’t think I should be explaining a birthday party with friends.”

Continue reading Henry Burris Bra Realness: Football Quarterback Wears a Woman’s Bra