i’d personally tuck the pant leg into the boots. i like this bag because it can be worn on the shoulder or crossbody, which is great for hands-free. I chose this waterproof bomber jacket instead of a trench for the orchard because a trench coat can look like too much fabric in photos, if you plan on taking family/content pictures or it can feel heavy since you’ll be walking with boots and a bag of fruit 🍂🍎🧺🫶🏼