Welcome to the Lounge, sonorlite! I hesitate to recommend hats to people. I know what I like. Thin ribbons, wider brims, and crown bashes that have nice lines to them. Doesn't narrow it down much. I tend to like light greys and earth tones, too.
I think you could wear almost any style with that jacket. Gray or brown tweed caps, herringbone patterns too.
Brown fedoras or one with a contrasting ribbon.
I'm seeing a larger brim hat that you could wear with a serious tilt. Just my first impressions though, I don't think I've ever seen a leather jacket/hat combo I didn't like.
Welcome sonorlite, I agree most anything would look good with that. I think a tawny fawn akubra or other brown would look good maybe not the same color as the jacket.
Deanglen that avatar looks like a million bucks! I may not have been paying attention but i think most of your avs have been darker shirts and hats.
With the fitted waist and medium collar and lapels, I would recommend a "medium" brim, something in the 2" to 2 3/8" range. While a rich brown might be the first choice, you could also look at a lighter tan, or even taupe (or brownish grey) with a black ribbon.
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