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you will not want the overboots. that is a specific condition item, like butt ass cold and requires crampons. I doubt that you will be or want to be in crampons for the whole day. I doubt your guide will allow you to use them. I had super gaiters and snow will sneak in around the rubber rand and you r boots will get wet anyways. I have guided in cascades for 8 years and very familiar with slogging up volcanoes around here. You will be glad to bring double plastic boots over leather. Leather boots are fine mid july and on. You can get by with leather boots (history has shown that old timers climbed plenty of bad ass shit with loafers) but you will be much happier with something that you can remove the liner and dry out daily.

Trip: Mount Hood - Pearly Gates, South Side Trip Date: 05/11/2019 Trip Report: Getting there: Left Seattle area around 7:30 PM Friday 5/10, we got to parking lot in Timberline at 12 AM. Several parties were departing at that time towards the summit, my partner and I decided to sleep a couple hours before. We slept until 2:30 AM and set out towards the summit at 3:00 AM. Conditions: Snow starts from parking lot, no need for snowshoes if climbing at night. We put on crampons at 7200 elevation because it was getting icy. Upon reaching the hogg's back we chose to follow the crowds and went via the Pearly Gates, it's very icy there now and extremely crowded. Crampons and ice axe and helmet is all you need. some people had ice tools, but it's unnecessary. I counted at least 200 people climbing through out the day on the mountain. Summit: We got to the summit at 8 am. Gorgeous views as it was a very clear day. Return: We attempted to go down via Old Chute to avoid the bottleneck in the pearly gates. Some people were climbing via old chute, but I decided to explore a different route alternate path right next to pearly gates, this proved to be an excellent choice as it avoided bottleneck and felt safer than the old chute. Stats: 5 hours from parking lot to summit ( we were going very slow). 2h40m from peak to car. Last 2 miles felt like forever as you see cars very near yet very far. 5100 feet gain. 8-9 miles rt, can't really say as gps was acting up. https://www.instagram.com/iron_knee/ Gear Notes: Ice Axe, Crampons, Helmet Approach Notes: Paved road all the way. Snow stats from parking lot.