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That One Item Everybody Tells You Looks Good On You, But You Don’t Believe It [PHOTOS]

Barry's Hat
Barry’s uncomfortable hat

Everybody has one or two clothing items that everybody says you look good wearing, but you don’t think so. We all perceive our looks different than others do, so just go with it?

Why do we have such a hard time believing others when they tell us we look good in something, and we think we look hideous?  You really want to be able to wear that pair of pants, or shirt, or whatever…but there’s just something about how it wears on you that you don’t like, but you bought it anyways.


I’m my own worst critic, like most of us are. My wife won’t shop for me because I’m as particular as it gets. Especially pants, forget it. They’ll get returned to the store. I love wearing ball caps, but most of them don’t fit right and look bad on me. Out of 100 hats I could try on, I may find 1 that I like and end up not wearing it because *something* isn’t quite right about it. My head is small and shaped odd, so every cap is way too tall on my head.

The cap above is what I’m wearing today, and I love how it looks on the shelf, but don’t believe it looks right on my head. Everybody I’ve asked said it looks good and I should wear it more often.

Barry's hat again
Barry’s hat again. Argh

I think I’ll force myself to wear it more often and try not to be so picky. It’s your turn to do the same. Sometime this week, put on something that’s in your closet that you’ve refused to wear (that people say looks good on you), and wear it. Then send the photo to me and we can overcome this together. I’ll gladly tell you if I think you were right.

We’ve made it very easy to send the photo, just download our 98.1 app and snap the pic and send it to me! Here’s the link to download it if you haven’t already!

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