Can You Give Unsolicited Fashion Advice to Interns?

Ever had the urge to indulge your inner Anna Wintour and act as the fashion police?  Reader M has a question along these lines…

Can we do a story on the extent to which permanent hires (i.e. me) can give unsolicited fashion advice to interns?  I have worked in private practice for a number of years and am now at a government agency.  Many of our female interns are taking the casual dress code here to the next level – “jeans Friday” does not mean your favorite yard work jeans, a sleeveless plaid tank, and Old Navy flipflops (I’m wearing dark wash trouser jeans, a Calvin Klein polo with bloused sleeves, and Cole Haan suede/patent skimmers).  Many of our interns, let’s face it, would rather be in private practice but are spending their summer with us due to the economy.   It’s more painful because the male interns are appropriately dressed (although I know it’s easier to pick out golf attire than a female jeans Friday outfit).   Can I / should I say anything in the way of career advice?

How do you tell someone their outfit isn’t working — or worse, that their entire style needs to be rethought?  It’s a difficult question — and i think we’ve all been on both sides of the issue.  This blog partly grew from my frustration over this — both a) realizing belatedly that I’d been wearing completely inappropriate things, and b) not feeling able to say anything when I saw other women making fashion gaffes and wearing the “are you kidding me?” kind of outfits I saw at various points in my career.  With summer, the flood of interns from colleges, law schools, and grad schools makes the problem only more magnified.  When should you tell someone that their outfit is totally inappropriate? [Read more…]