I have a friend who dresses totally inappropriately. She wears clothes that look awful on her all the time–dresses that are too short and are unflattering for her figure (she’s not fat, but she’s not thin, either), belly shirts, really tight things that show her pooch, or skinny jeans that just aren’t a good look. It’s like she dresses herself in whatever is trendy without even thinking of whether it will look good on her body. 

How can I tell her that she’s making herself look bad? I think if she dressed better she could look really cute, but short of telling her something isn’t working when we’re out shopping I don’t know how to bring it up. 

-Just Trying to Help


Let me ask you this: WHO are you trying to help, your friend, or yourself?

I ask, because it sounds to me like this isn’t really about your friend’s welfare; it’s about you feeling superior by negatively judging other people based solely on appearances. You don’t mention whether your friend is happy, or funny, or has a great job, or is the most loyal person you can hope to meet: you’re harping exclusively on how she looks, possibly the least-important aspect of who she is.

Of course you might very well be right. Your friend might look better if she wore stripes that went in a different direction, stuck to peplums even if they’re no longer the newest thing, and bought a better-fitting bra (actually, all us ladies should buy better-fitting bras). And you’re not alone. I definitely make snap judgments on people’s appearances. I think we all do–that’s why it is legitimately important that you present yourself well. Throw on whatever is on your floor, regardless of size or smell, and you’ll provoke a certain reaction in people. Only ever wear polo shirts and pearls, and you’ll get another one, totally different, but equally specific.

So here’s another question: do you think your friend’s chosen style is holding her BACK in any way? Is it harming her professionally (because what you wear to work or an interview will affect whether you get, or keep, the job)? Is it hurting her chances at finding someone (only an important factor if she’s LOOKING for someone)? Is her look ever indecent, or just something you think could be way more shmangin’ with a little extra effort?

If you really care about your friend, try turning off the judgment that’s about whether a trend looks “best” on her, and especially about her weight (not necessary, never helpful). But if you think her look is holding her back in an important way, try to tell her that, gently.

It’s not about whether or not you like her in a belly shirt. It’s about whether you like her enough to know the difference between your own hangups and a legitimate problem for someone else.