What outfit was the hardest for you to put on a doll?

The dollfie dream Anthy dress!! What a nightmare. I never figure out some of the pieces

 

Isao Nanjou 1st's fullset...so many chains, belts and buckles...

 

Honestly, any outfit that uses lace in place of eyelets for lacing. I have a Luts outfit like that, a Sartoria J outfit as well. I have to use a crochet hook for the Sartoria J outfit which really means asking my mother to do it because I have no idea how to use one. Some of my Volks outfits came with extra ribbons that I have no idea where they go.

 

I have an Iple outfit... a black pleather catsuit, essentially. It was made for SIDs, but is *just* stretchy enough to fit Kestrel, my EID girl. Getting it on her, though? Yeah. Not an easy process. It looks fab on her, though.

 

All my dolls dress casual for a reason I have 0 patience when it comes to dressing them.
I used to have 1/3 sized dolls wearing Lolita and layered dresses with frills etc and took me a lot of time to realise that I didn't wanted to buy clothes for them because I was avoiding getting them changed.

Still I have a little White Rabbit outfit for my YoSD that I adore and is safely storaged away because it gets me on my nerves to put them a frilly shirt.

 

I'm having nightmare flashbacks to DollHeart's Fer coats and about a thousand itty-bitty buttons.

 

I don't purchase readily made doll clothes for my dolls in general, but for my BJD I have never done so. So, I never had any particular outfit that was made to be a pain in the gut to place on the doll. However, I purchased my first mature tiny last year and dressing him in just about any clothes is a real struggle. I now understand why little girls rather not bother with fully posable Barbie and those are not strung together. Having tiny spread out fingers doesn't help; the hands look beautiful and detailed but it adds to the nightmare inducing aspect of dressing him, for me. I probably shouldn't keep (attempting to) making realistic, detailed clothes that are form fitting for him. I never had any issues dressing my 67cm male, and he made my arm numb from how heavy he is to hold for a just a few minutes. I'll probably never own another mature tiny BJD, for many other reasons, but dressing the one I currently have is an actual pain in the lowet back. DX

 

My dolls dress casually mostly, but just today I had to cut the strings in one of my boys because he was strung so tightly that I couldn't get his hands off to get his shirt on him. Then I had to restring him with looser string. So I'm going to say that was definitely towards the top of my "pain in the ass" list. Another was a Tree Design corset that had to be almost entirely unlaced to get it on the doll, then relaced. I ended up selling that one even though it was gorgeous on my girl because it just wasn't worth the hassle. Lace shirts, loose knit sweaters and ripped jeans are also kind of a pain when fingers and toes keep slipping through the holes and getting caught.

 

I have a few doll sized t-hirts that are doll convention merch, they are fully closed in the back and so require head removal. I rarely use them, but they are nice souveniers.
I make most of my own doll clothes, so I usually make them withing my tolerance for inconvenience. But I do have a few outfits that are a bit more involved simply because they consist of many parts, some with tiny buttons or ties. I don't use those very often.
And there is always the fingers catching on knitted and crochet cardigans and the like, but there are workarounds for those, so that's ok.

Over all, I rather enjoy redressing my dolls.