As much as I hate to say it, you need more shoes (or boots). If you are a walker, hiker, runner, cycler, etc., you need proper shoes, and specific shoes for the activity. Now is a great time to assess the quality and quantity of your footwear. I add quantity to that because it never fails, any shoe I buy, it fails at least one requirement, so I'll buy 2. I need something comfortable, waterproof, skid resistant and warm... oh, and in a size 5 1/2 wide. The rare time I find the "perfect" boot, I will go back and buy 1 or 2 more to have in case the first gets worn out or wet and because it's so hard for me to find something that fits.
Shoe stores are clearing out and moving in new stock. Take advantage of those sales. Many stores have frequent shopper discounts as well. Many of us are getting our tax refunds back too. Did you get a gift certificate at Christmas and not use it yet? If there's not a sale, have you thought about asking a manager to knock a few respectable dollars off? Even if it's only $10, you can use that to buy some new socks. Having the proper socks also will aid in the comfort of your activity.
The wrong footwear can lead to all sorts of injuries, including falls. Safety first. You want to have fun on your weekends and vacations. Hospitals are nice and all, we just don't need to include them in our destinations.
