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Boyish sissy outfits
#1
What do you think would be the most suitable outfits for a sissy-ish boy who isn't being feminized or an outright adult baby or little? 

You can specify different outfits for different circumstances like at home, nighttime, discrete out in public, punishment and so on if you want. I'm really not very creative with things like that so beyond a school uniform (which isn't even a thing in this country) I'm hitting a blank.
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#2
A Lord Fauntleroy suit maybe? Definitely in the realms of sissyish but strictly speaking a male outfit.
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#3
I had to look that up 


That would probably be one for in the home or formal occassions maybe Blush . But indeed very cute!
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#4
The Lord Fauntleroy suit is a something I would suggest but also how about a traditional Scottish Piper or Irish Step dance. Swiss or Greek guard.
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#5
Anything with a SKIRT - PEPLUM - frilly/lace detailing - with a hem line that with little or no effort shows panties or a diaper cover.

A pastel blouse with pearl button detailing and of course the button placket is reversed -or- a more impossible back button closing.
Billowing puffy sleeves - hem resting just at the waist (no tucking).

Shoes - why or course mary janes with taps and filly ankle detailing sox - with optional jingle bells.

And to top it off - perhaps a beret hat !  

Or on another note - a Fustanella outfit - - - image

   
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#6
Babylock is definitely on to something there with the descriptions and the image is something I had in mind. It’s also a fascinating history behind that outfit. Simmilarly with kilted outfits I mention. Their are images in the Irish version just like the Greek that are definitely closer to skirt than a kilt and I’m not referring to the girls outfits which are also lovely - yes slightly off topic, I know.
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#7
Thanks for the suggestions! I really like the fustanella outfit.
I hadn't really thought about regional, traditional dress yet, but that's certainly an idea.
The problem with a kilt is that they've never been a thing in the Netherlands, everybody would just assume you're dressed up as a Scotsman for Carnaval.

Inspired by this I did a little research into Dutch traditional dress, even though that's mostly associated with places in the (protestant) North.
And it's much as I expected: farmers and fishermen, so the outfits are rather functional and agrarian looking: long pants, woolen sweaters, coats. It looks more stern than cute and sweet. Same for the women actually.. they look intimidatingly stern!

I did find out that the traditional dress used to be extremely prescriptive though. With very specific outfits for specific occasions such as church, but also really extensive rules on what to wear during mourning, with a bunch of different severities and phases. Different outfits denoting your occupation and so on. That's kind of interesting.

Unfortunately, there has always been subtle but huge cultural divide in the Netherlands between the protestant North and the catholic South where I'm from. So these outfits look just as foreign to me as a Lord Fauntleroy or Fustanella suit.. I suspect my region simply didn't have much of a dresscode.. it was mostly very poor farmers that were probably happy to be wearing something, anything!
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#8
How about a sailor suit?
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#9
A fluffy jumper (sweater) or cardigan could work, particularly in a lighter colour. Pastels maybe? Think soft angora or mohair. Or a thick, Aryan style, with plenty of cables and even baubles. Baubles look so feminine.
And to really play on the mind, the cardigan could be a female one, meaning the buttons do up on the opposite side. That, in its subtle way, would suggest to the observer that something wasn't 'quite right'.
And the garment would have to be worn with shorts and long socks. Shoes lace-ups, highly polished. Haircut very short.
Worn with shorts and long socks (to the knees). Shoes highly polished, lace-up only.
Underwear panties, with a very feminine spencer under the jumper or cardigan. That way the boy wouldn't dare remove his jumper or cardigan.
Know thy self, sissy.  Don't whine, don't pine, learn to expand your mind.   
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#10
Short-alls, or dungarees depending on your location. Very juvenile and after a certain age relegated to mostly girlswear.
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