The present invention employs chimneys and chimneys structures to move or vent heat and moisture away from the foot and out of the microclimate of the shoe. The chimneys define pathways that utilize convection and other principles to cool and dry the foot. The chimneys and chimney structures can have many different configurations, and can be positioned anywhere desired in the upper. For example, chimneys can be positioned on the sidewalls of the upper, in the tongue, or both. Chimneys and chimney structures can also be used with form-fitting foot coverings such as socks or leggings, or used with other apparel. Specialized footbeds can also be employed with footwear chimneys to evacuate hot, moist air away from the underside of the foot and towards the chimneys.