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If you look at my avatar of Howard Hughes you'll see a casual look that can be duplicated and is not screaming "antique geek!" He's got slacks on probably gray but tan chinos would be fine. He wears a dress-type shirt with no tie but with a tie he would look good too. The jacket is a waist hugging commercial leather model. You could substitute several non-leather short jackets/windbreakers that timelessly have looked about the same for 75 years. The hat in gray puts it all together but with tan pants a brown or tan hat would work.
Technically nothing except the fedora dates the photo. Without the hat if you dressed that way there wouldn't even be an extra look on anyone's part. Add the fedora when you feel a little bolder.
Technically nothing except the fedora dates the photo. Without the hat if you dressed that way there wouldn't even be an extra look on anyone's part. Add the fedora when you feel a little bolder.