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Again the correct answer is yes and yes. I'm not a hat person either but wore one daily on CF last year and again daily on CP this year. Necessary items of equipment.
Look at Title Nine they have shorts that you could wear underneath skirts but also have some quick dry skorts. I prefer them over Athleta due to fit and how long the clothing lasts.
Try on and take a look at the Dueter 34L. REI sales clerk suggested it along with the Gregory. The Dueter fits like a dream with great airflow. There are small pockets on the belt as well. You might be surprised at how well you like it
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