What's your favorite sissy outfit? (2024)

We all have fun sissy outfits we like to wear, but I’d like to know what your favorite is. To answer my own question, my favorite sissy outfit is a frilly pink dress with a pair of white thigh-high socks and a diaper underneath. I’ve also been wanting to try makeup, but I haven’t done that yet. What about you, though?

Had a few days away last week wearing my favourite sissy dresses. I like them short to show off the frilly pants. So its starts with a good nappy and plastic pants. Then tights either white or pink. The frilly pants go on next.
I have some very full petticoats, and then the short dress to show off everything underneath. Frilled ankle socks and suitable shoes are then added.
I have a couple of wigs, the past the shoulder blond one being my favourite. My friend does my makeup which I enjoy very much. I add pink bows to my wig, often a simple necklace and I even have an appropriate watch with a pink strap.( See Below) Its the little details that make it fun.

Quite similar to yours! White thigh high stockings with pink bow on top with my matching pink goodnite diapee

well my femboy outfit is just thigh highs, arm warmers, a skirt that hides my diaper and a cozy top

Never really gone baby sissy, but love the rock chick look, so boots , black tights, denim mini-skirt, jacket & wig - gone out for a few late night strolls like that with my nappy not too well hidden under my mini-skirt and tights.

2 of my favourites are my wittle pleated school skirt with knee socks or my tykes skirtall with just a onsie on below... ohh and of course my crinkly nappy hehe

I like costumes -- my favorite outfit is an Alice in Wonderland dress, with white tights and a diaper underneath of course.

Definitely this outfit...

Oh and this...

Basically anything with a Peter Pan collar!

I have an Alice in Wonderland dress (which I love)...
It's SO difficult to choose just one outfit!

OOOOOOOOHHHHHH—-OOOOOOHHHHH! THAT’S A CUTE OUTFIT! ALMOST MAKES ME WANNA GO DO SOME SHOPPIN’! I REALLY, REALLY LOVE THOSE SOCKS WITH IT!

My favorite sissy outfit that I wish I had would be either a cheerleading outfit or a school girl outfit.

Who doesn't love a alice in wonderland dress

I have some satin panties with sissy all over them and a matching dress? I like wearing those and love wearing the underwear my wife wore the previous day,

As I have posted many times, my favourite fem/sissy outfit state of mind along with my public school girl uniform is my 9 month pregnant state… pics attached.
I am wearing a very realistic silicone 9 month 3.5 kg belly, maternity panties, maternity bra, maternity long sleeve black top and maternity black opaque tights that go way over my belly.
Underneath my clothes, I am strapped into a maternity belly belt that goes under my puss*, between my big fat pregnant legs and over my shoulders and holds me in.
Then as you can see I am wearing a denim maternity dungaree.
I love wearing this outfit so much and sitting in it for hours because it reminds me of what a women goes through.
My wife and family are away for 3 days and so I have made myself 9 months pregnant from the time of writing this for the next 50 hours x
Preggo Steph