Jack is a snappy dresser. With his strikingly handsome face and lean, athletic frame, he would look very natural in a fashion spread shot on location in a southern European resort town. Instead, we shot his pictures in the Princeton High School stadium with a junior league football game on the field. His mom had planned his session months in advance, getting clearance from the administration to use the field after most sports seasons had wrapped, and the field was scheduled to be free. Except it turned out that it wasn’t. We thought maybe if we waited it out and took pictures at the high school, maybe the event would be over soon, but as sunset approached, it became clear that wasn’t happening in time. So at the last minute, we decided to crash the field and claim a little unused corner of the track with Jack still dressed elegantly enough for the Derby. And it was all fine, because when someone looks this good in a pinstriped seersucker blazer, it really doesn’t matter where you shoot his picture.
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