latestOutfits & Style

Gorgeous Crossdresser Penelope Shares Her Favorite Outfits to Wear

Crossdresser Penelope shares her favorite outfitGorgeous Crossdresser Penelope “Penny” Rose from San Francisco, California shares her 5 favorite Outfits / Style to wear.

Some words by Penelope:

“Hi, I’m Penelope (but you can call me Penny 😉) and I’m here to chat about my five favorite outfits. I find it incredibly hard to only pick five, there’s just too many looks and styles that I love to present myself in. There’s also some outfits that I really love that are a little more out there and that you can find on my various socials. With all that said, let’s have a look at the ones I have chosen..”


Outfit no.1

Crossdresser Penny in little black dress
“Let’s kick things off simply with this adorable black dress. Given its shortness I’d count it as an LBD but the sheer size of the skirt makes it more of a statement than a regular, more figure-hugging LBD.

The skirt is the main appeal of this outfit for me though; it’s very flattering because it hides any extra pounds you may carry on your waist under its abundant poof, it is short enough to show off your slim legs perfectly which creates a great contrast and its shape is just inherently femme while maintaining a level of girly playfulness. Pairing the dress with shiny black nylons and black pumps completes an elegant showstopper of a look.”


Outfit no.2

crossdresser in blue pencil dress
“I love how cute this outfit makes me feel. The pencil dress hugs me in all the right places (without being too tight) to show off my curves and the belt further accentuates my waist, making me feel all the more femme. But apart from the flattering shape I also like the striking blue/red color contrast between the dress and the belt/heel combo. I like how this is a bit of retro look without feeling old-fashioned.”


Outfit no.3

crossdresser in jean mini skirt and pantyhose
“This outfit feels cozy, casual and a little playfully sexy which makes it one of my favorites. The long-sleeve bodysuit gives me serious fall vibes (where’s my pumpkin spice latte???) with the denim miniskirt adding a fun girl-next-door vibe while showing off my nylon-encased legs nicely. This is something I’d wanna wear when I’m having a fun day out with my gals. Looking at this pic makes me so utterly happy, just look at my smile!”


Outfit no. 4

Crossdresser in vintage dress
“When I wanna indulge in my more housewifey side I love to don a vintage A-line dress (of which I have way too many 😂) and combine that with at least one petticoat to give it the retro poof look I’m after. This outfit in particular I combined with a little bolero style blazer for some layering and to create a decent contrast with the salmon color of the dress.”

And of course, you need to wear heels and nylons to really complete the look. It may be hidden from view but I’m wearing a garter belt to hold up my nylons which doesn’t really add anything to the overall look (unless you wanna be a little naughty and give someone a peek 😉) but the feeling of it is yet another reminder of how wonderfully feminine you get to feel in this ensemble.”


Outfit no. 5

Crossdresser in latex skirt
“This is an outfit that makes me feel absolutely fierce and dominant. Black is always a good color to work with, and combined with the appropriate materials it can create such a dominant and exciting look. In my case this means a latex skirt together with a wide belt on top of a sheer, bedazzled bodysuit that cheekily reveals the black bra I’m wearing underneath.



The outfit is completed by my shiny stiletto platform boots, oily-looking black nylons and a blingy wide choker. Wearing this makes me feel like such a boss, that’s why it’s one of my favorite looks.”

Follow Penelope on Instagram: https://www.instagram.com/penelope_penny_rose/

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