DEAR HARRIETTE: My best friend has no idea how to dress. Whenever we go out, she wears something ridiculous or inappropriate and embarrasses me. Sometimes the outfits will be out of style, or they’ll make no sense whatsoever for the occasion or weather. It's really getting out of hand. I don't want us to stop doing things together, but I feel like I'm not a real friend if I don't tell her how she looks. I also don’t want to come across as a hater because I know how it would sound. What do I tell her? -- Truth Hurts
DEAR TRUTH HURTS: You call this person your best friend; now it’s time to show her what that means. Instead of privately fuming about her wardrobe choices, tell her that you are concerned that she often seems to miss it when it comes to dressing for the occasion. Tell her that a lot of these activities have unwritten dress codes -- not that she has to be a cookie cutter of others, but more that there are parameters that she may want to consider before getting dressed. Ask her if she is willing to talk about this with you. If so, gently give her some examples where you believe she missed in a big way -- and why. Especially when you thought how she dressed was inappropriate, explain what went awry until you are sure she understands it.
Also, know that your friend may just have a quirky personal style and doesn’t want to conform to whatever standards the moment calls for. If that ends up being her stance, you will need to figure out how to accept her for who she is, weird wardrobe and all, and stop being embarrassed. Let her be her.