Be trendy if you like. Here's why.

We hope you think Squaredy Cats are more than just trendy. We want to stick around.

We couldn't think of any trendy looks that would still remain semi-generic so that this cat would make sense as a representative for more than one specific trend. We just picked the "backward baseball cap" trend. Very basic.
The thing about trends is that they are looked at as style by some people, and viewed very negatively by others. Though, from the outside a trend may seem annoying, we all struggle to find out who we are and what we like. Giving in to a trend now and then is an easy way to see if you want to fit in or stand out - or a little of both.
Be a trend-setter or a trend-follower, or be wishy-washy about trends. If you like it, it shouldn't matter if it seems to others that you give in to outside influences. Isn't their judgment of you just another outside influence? Forget'em. Be trendy if you like.

not squared to charge it

The art for this one has always been the same, but the caption was originally "not squared of coupons."
The idea was that shoppers shouldn't be afraid to use coupons to save money, but the more we looked at it the more we realized this image doesn't really look like someone who is a super-saver. She's simply a shopper. She's fully equipped with her credit card and designer bag. Chances are she doesn't really car about coupons. She's not squared to charge it.