I had a similair experience with my son at the same age. He would sneak to put my shoes on and even went as far as putting my underwear on over his clothes. (sometimes at the same time!) It was always when I was distracted with school work or on my cell phone. It happened a couple of times, when we finally got to the bottom of things, he said that it was because he wanted to work in the office like the other girls do with me. We put him in hockey and set aside that time every week for just him and the guys... and now he's ALL BOY! lol... I wouldn't worry too much, maybe he's just looking for some attention. I also agree with the prior posting, you need a new speech pathologist... or they need to try a new approach with him. I think the events are unrelated.
spelling error: dysfluency should be spelled disfluency.
I agree that your son's dysfluency of speech is not likely related to the behaviors that you have described. If you do believe that his dysfluency is worsening you should have a discussion with the speech/language pathologist treating him.
I agree also that the behaviors may just be a case of emulating those that he has the most exposure too. My five year old, has put on my high heels. He also likes to try on his sister's pink knit cap and scarf. When I fixed her hair yesterday with a clip, he stated " I want beautiful hair, too". He tried to remove the clip which I promptly stopped him. He also likes to play with Care Bears, baby dolls and My Favorite Pony. Other favorite activites include, bike riding, climbing, sliding, playing in the sprinklers. He clearly expresses a preference to be around other boys.
I agree with the above posters that this behavior is cause for concern. Perhaps in additon to the above suggestions, it could be arranged so that he could spend alone time and/or a special outing or activity with dad or another adult male whom he has a close relationship.
Best wishes...
typo: I don't feel that this behavior is cause for concern.
I rather doubt your son's recent behavioral changes have much (if anything) to do with his speech difficulties. I would be more inclined to believe it is a simple, transient case of "emmulating a loved other": you and/or your daughter, for example. If, for most of his day, he is exposed to his mother and sister, he may pick up some mannerisms and model them. At 2.5, "wanting to wear mom's (or other adults) shoes" is not at all uncommon, nor is it a cause for concern. You may want to consider entering him in a play group or pre-school type setting where he will be exposed to other boys his age so he will have other behaviors to model, as well.
Get a new speech pathologist if possible to work on his speech.
I would not concentrate on his behaviors - that could be a phase right now, however, if you don't want him wearing your shoes, tell him these are mommy's things and you don't want him to wear them.
Is he in school right now, or has he not started kindergarten yet? Sounds to me like a phase, and maybe he could use some more social interactions with kids his age. Best wishes!