In October 2025, I did the 38-mile Roundabout Trail in one day . When you're facing a 14-hour endurance hike, what you wear isn't just clothing — it can mean the difference between smooth sailing and show-stopping blisters. In case you don't want to read the full post, here's a quick summary: 🥾 Category Recommendation Why it Went the Distance (38 Miles) Shoes Merrell Women's All Out Blaze Aero Sport Lighter low-top design saved my knees from lifting heavy shoes 80,000 times. Socks Wrightsock single-layer quarter socks These prevented me from getting a hike-stopping blister. Pants (cool weather) Affordable leggings The perfect weight for long days in standard SF weather. Pants (warm weather) Moosehill quick-dry zip-off cargo pants Lightweight insurance against rain or unexpected heat. Base Layer REI and Smartwool are both great Keeps the core dry and allows for easy temperature changes. Arm Sleeves (cool weather) Fleece sleeves No need to stop and de-layer! Matc...