I would imagine it does. I had a small whistle and it fit over my shoulder. I have a skinny upper body. I would imagine it might be a tight squeeze over a coat. The leather on the whistle is absolutely incredible. I would go for it. There's been quite a few on eBay from hgbags and she's an awesome seller. I bought my twiggy from her and it's gorgeous.
I started a thread about whistle bags afew days ago. I didn't see any pictures of people wearing the large whistle (that's the one I'm interested in also). It looks so cute and the leather looks great. I'm just trying to decide what to do?????!!!!!