This was a listener question.  She wanted to know how to have a difficult conversation about someones appearance when they were not or appeared not to know how to dress for a particular occassion or just work.  Here are my top tips; 
Establish what the issues are:
Smell?
Clothing style or fit?
Lack of knowledge or understanding about clothing norms?
Hair / make up / shortness or exposure?

Establish and write a company dress code policy.  
Make a time for a casual meet up and find out a bit about them – what are their values and are they in a position to fund new clothes or pay more attention to their appearance.  
Ask them if they have noticed what others wear to work around the office
Talk to the person on the day that they have dressed inappropriately, in a confidential setting & tell them that their attire may be perceived as inappropriate
Define casual Fridays so there is no confusion about what to wear
Talk to the person in person not over email
Always speak in private
Be clear on what the problem is and explain why
Be positive about other aspects of their job and reassure them that they are not going to lose their job
Act quickly as soon as the issue arises
Don’t get personal  - talk about work standards and the image your company is is trying to portray.
Help them with solutions
 
Best of luck and keep the feedback coming.  

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