I couponed for a while a few years ago. During that time, I organized the inserts by type (Red Plum, Smart Source, P&G) and by the date the insert came out. I followed a couple of couponing blogs that would match the coupons available with the sales that were going on that week at several different stores. That shortcut made it easy to pull the inserts and clip the coupons that I needed before each weekly shopping trip. I stuck my coupons in a single envelope and took it and my shopping list to the store. It wasn't hard to do, but it didn't make for a quick trip either and I had to go to multiple stores. I saved a ton of money, but I also bought tons of stuff I didn't need.
Now, I load digital coupons onto my store card. There's no need to clip them and I don't have to worry about forgetting them at home. I don't save as much money with this method, but I don't spend as much money either. The only thing that's easier is shopping online and using coupon codes.