So one little money saving shopping trip I have been taking advantage of is shopping for Clearance items at the end of season, and save big bucks. Unless you know for a fact that you won't be able to fit into something (still a growing child, child bearing, or losing weight) go ahead and buy something that you know you will most likely be able to use the following season, but with the discount of the clearance sale. Last year, I found some great boots that I really loved, and the best part was the it was just in time for Spring/Summer and thus I wouldn't need to be wearing them for a few months, but since the store was trying to get them off the shelves, they were a steal practically. Same with some sandals, that were on clearance. Shoes that normally would be a lot more, I got for less, way less.
Unless the item is perishable, seriously, buy clothing at the end of the season, and then save it. Your wallet will thank you. I almost never buy clothing when it first comes out, unless there is a very special promotion going on in order to get people to buy in the first place. It may feel a little weird to buy something when the next season is coming up, but hey, if the shoe fits (until next season) then buy it and have some extra dolla to go out on the town!
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