Sissy Dress

This is a beautiful and intense way to cross dress. In fact it's far more than just cross dressing because you're not just dressing like a woman. You're dressing up to look like a little doll. This makes it one of the most extreme way to change your appearance. There is nothing quite like the transformation of an adult man into a pretty little doll with all the frills and decorations.

You probably won't find this outfit in regular clothes shops but there are specialized online stores for cross dressers and these often have a whole department dedicated to this outfit. You can order these dresses plainly wrapped and it's much more likely that these online shops have the right dress size for you. Some shops also take custom orders for their outfits so you can get exactly the dress you're dreaming of.

This outfit is from

About this Outfit

Most commonly, the sissy dress is decorated all over with ruffles and lace. This decoration is nearly always massively exaggerated as it is with dolls. Often you have ribbons and bows all over or at least one large bow at the bust or at the back.

All colours are possible of course but there is an overwhelming preference for light pink and pastel colours which are typically complemented with white ruffles and petticoat. These colours give an overall innocence in appearance (that’s why they’re also my preferred choice for guys who cross dress).

Satin dresses are the most popular and the ones you’ll find most often in stores but there are many other possibilities. I’ve even seen PVC versions! To me that’s a major clash of characters but some people obviously like it.

Another popular feature is the puff sleeve which is again highly exaggerated. I would think that most of these dresses have puff sleeves of varying size and length. It’s a kind of ‘must have’ for the doll outfit.

As you can see, it’s hardly cross dressing anymore because women basically never wear anything like this. Hell you won’t get me into one of those outfits even if it was for a costume party.


  1. Petticoat: A sissy outfit is unthinkable without a petticoat. Not just a little underskirt but a very full petticoat that makes the skirt stick out almost like a tutu. This effect is enhanced further with ruffles or fluff at the hem. If you’re shopping for a matching petticoat, you’ve got to make sure the sizes are compatible or they won’t work together at all. Any common materials are ok but many guys particularly like taffeta because it rustles so loudly. Others prefer a softer material like chiffon. You can buy these in dancewear stores or specialized shops. See my article on petticoats for more.
  2. Tights: Another must have for the outfit. The tights are nearly always white and many prefer suspender tights. Both of these, but especially the suspenders really need smooth hair free legs. I can’t emphasize that point enough. The effect is great when done properly. Buy them in any retail store.
  3. Shoes: High heels are not very common and don’t quite match the doll like character of the sissy outfit in my opinion. Better are those ballerina style shoes that we’ve been seeing around a lot lately. They aren’t real ballet shoes but have that little bow on top and practically no heel. Shoes are harder to find because of the limited sizes available. Your best option is a specialized cross dressing store.
  4. Hair accessories: If you have long hair, then a big pretty bow is great, or best of all, bunches with bows or pig tails. Basically everything that looks like a little girl. Otherwise a wig is one alternative and many like to take it even further by wearing a bonnet (so cute).
  5. Pettipants: Not so essential because you can’t see them under all the layers of ruffles and petticoats but they do kind of make the outfit complete. Pettipants are made to go under petticoats and have their own ruffles on them (yes, even more ruffles can you believe it). Most shops that sell a variety of petticoats will include some pettipants as well. I wrote an article for more on pettipants. Alternatively go for the wider range of sissy panties.

A variant of this outfit is the sissy maid. As this is a role more than just a costume, I decided to write a separate article on the sissy maid.

For some more intensive fun with sissy clothes and role play, check out Sissification, Petticoat Punishment and forced feminization.


Other crossdressing outfits:

Male Corset

Adorable Crossdressing Outfits

Favorite Crossdressing Outfits

Men in Petticoats

Men in Tutus

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