To me this seems to be from the same TATLER 1987 session.
According to www.contactophoto.com who have all the Herb Ritts Outtakes this shoot took place on 31st May 1987 but to me the hair and makeup look the same has the Rolling Stone photoshoot that took place in June 1987 in japan i dont think its from the True Blue photoshoot at all because her hair was a little longer in that shoot just that i'd share what little info i have ;)
Thanks for the comments. I checked the link you provided. Lots of the date information there is not accurate. I was just telling someone that if this photo is from 1987 I believed it was the session in Tokyo with Madonna in bed with the Minnie Mouse ears. Glad someone else thinks so too. Her hair looks exactly the same in both photos. Having compared HQ versions of both the Tatler 87 outtake and this one in question there are such dramatic differences in my opinion. Her hair color, styling, and makeup are completely different. Personally I think limefoto listed it incorrectly. It's happened before and even in print in Herb's last book they messed up on dates/places.
WOW! I never saw contactophoto link before, and even if the makeup and the photo lighting are completely different in the two photographs (the one posted and the TATLER cover), I though the hair color and size was slightly similar, but I forget about the ROLLING STONE 1987 session, and now I agree completely what onthecoverofamagazine said being from this Tokyo session.
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