TOUGH one. But if her dowdiness is so noticeable to you, it is probably verging on the inappropriate when it comes to upholding your company’s sharp and professional image. If she’s dressed in a mismatching, shapeless suit made of cheap material, those visiting the office may subconsciously absorb the idea that yours is a tired, careless organisation that doesn’t have enough self-regard to hire – or inspire – snappy staff. Appearance and carriage transmit all kinds of signals that people will not even be aware of until it comes time to sign a deal with you.
So it sounds like she does need a wake-up call. I’d strongly advise you not to criticise her outright. It could really undermine her, as well as get you in trouble if she complains.
I recommend this approach, assuming you have a decent relationship with her. Say you really need to go out and pick up something sharp for your wardrobe, as you’re tired of your current selection. Ask if she’d come with and offer advice and keep you company. Once in the shop, start pointing things out that would suit her well. “Oh, this would look amazing on you,” you can coo. See how she responds – she might start trying everything on that you pull out for her. Chances are though, she’ll cower and say “Oh, I couldn’t possibly.” But she might just get the hint. If she doesn’t, it’s fair enough for you to take her for coffee and bring it up gently but directly. Say you’re concerned about the image she is projecting, and while what she wears is her personal choice, if she wants to do her best at your particular workplace, you’d really like her to sharpen up.
The key is to be constructive. Offer to introduce her to an image consultant if you think the company would pay for it. Or offer to give some advice and tips. Most of all, don’t apologise for asking – as long as your reasons for doing so are professional, you are doing the right thing and she needs to respect that.