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Photos of my Kelly 40 Lakis as requested. I added a strap with a Kelly pocket- I decided when I got this bag (pre-loved 2005 model) that I was going to use it daily and not worry about scratches and wear and just enjoy the bag. The box leather is aging well and the marks have given it a lived-in look that I actual like and the fabric looks as good today as the day I got the bag. I baby some of my other pieces but this one goes back & forth with me to work everyday and it looks great- I have a 14.5” Samsung laptop which fits in - barely. That was a major driver when I replaced my old laptop earlier this year - whatever I bought had to fit into the Kelly 40
 
I was looking at one of their equestrian jackets and for once, it looks normal on me, but the back can billow a bit if I pull on it. They said it was normal for an equestrian jacket since it's meant to let the wind blow through. Has anyone encountered this with their RTW and am I just being sold a jacket that really isn't the right fit for me? Thanks for the advice gents (and ladies)
IMO it doesn’t sound like it fits (But I am not an equestrian). It sounds like you are buying it for fashion, so I agree with @justdennis84 that you need to love the fit. DH found H bomber jackets (not equestrian) really odd and billowy and short waisted, and he is average height and build.
 
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