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Without a direct side-by-side comparison, I think most people wouldn't realize these are two different hats. However, having your photos for a direct comparison, I'd go with the second hat--4-1/4" at the pinch with the 2-5/8" brim width. It's a marginal difference and you wear both hats well, but I think the dimensions of the second hat suit you more....OR / Wanderer conversion...4 1/2 inches tall at the pinch with a 2 7/8 brim...OR with Center Dent...4 1/4 at the pinch, but 4 1/2 at the highest point of the crown, with a 2 5/8 brim width...