As we’ve noted above, Chicago style is pretty casual, so you can expect to see a whole lot of jeans, tees, sweatshirts, and sneakers at a game. That said, throwing on a Cubs cap will certainly help you blend in (and drum up team pride). Depending on the season, it’s also smart to pack a sweater, wind breaker, or light coat, as Wrigley Field is famously windy thanks to gusts off nearby Lake Michigan.