From Hades Lord of the Dead: For some cases, it is necessary for Holmes to cross dress. Write a piece that explores his feelings connected to this. Go into as much or little detail as you wish.
I don't think this is quite what you wanted, but hopefully you still like it!
It was said that clothes maketh the man, but Holmes had long since found that the saying applied to more than just men. In his years of practice with the art of disguise, he well knew the value of a good costume and all it could conceal. The Woman was a perfect example of such. When she had dressed as a young man, he and Watson had not recognised her, passing her by with nary a thought. Even knowing she was an actress, and a very clever one at that, a simple switch of gender had hidden her completely from their sight.
Of course, even within the clothing options of his own gender such variety could apply. It had always been a particularly point of fascination to Holmes that by changing one's manner of dress one could so drastically impact their effect on the impressions of others. In fact, he had even considered writing a treatise on the subject. A sailor was viewed in quite a different way to a butcher, and both were seen very differently in comparison to the gentleman. Many of his cases would not have ended as successfully as they did if he had not used his skill with disguises to reach across lines of class, gender, and identity to become the person that was needed for the situation.
Often even when there was no such case to cause it, he would still choose to go out in disguise and spend some time in the persona of someone else. When Watson asked, Holmes told him that it was good practice, and it was, but that was not the entirety of his reasons. Sometimes, it was freeing to be somebody else, and view the world from a different perspective. After events with the Woman, ladies' clothes had entered his regular wardrobe of disguises, and one most useful fact had been discovered: ladies' sleeves were the ideal size to hide all manner of things, up to and including his pipe.