Question from Sherema in Orange Park, Fla.: "How do I tell my best girlfriend that the ton of makeup and skin tight clothes designed for teenage girls makes her a laughing stock at the office and not hurt her feelings? She is a very attractive 49-year-old lady, but her appearance makes it hard for our co-workers to take her seriously."
Lissa's Answer: You don't tell her that. If you sincerely want to help your friend bring out the best in herself and succeed at the office then show her your support. When your co-workers laugh at your friend, point out just how great she is at her job, and offer some specific examples of ways that she has contributed. Your friend deserves respect for her efforts, and should not be judged by her appearance, which she may very well like just the way it is.
If you think your friend is open to some changes in her wardrobe and make-up, take her shopping with you one weekend. Steer her towards outfits that would both flatter her and be office appropriate. Say things like: "That dress would look great on you! With your legs, wow! What do you think? I'd love to see it on you!" And then pick out some pieces for yourself to try on, too, so that you're going through this process together. You might comment on a particular combination that she models: "I like this for the office, it's so professional, and yet has a lot of personality. It suits you!" Your encouragement may give her the confidence to embrace a new look.
While you're at the department store, suggest the two of you get a make-up lesson at your favorite cosmetic counter. You could say: "I saw a great stylist talk about the new seasonal colors on "Good Morning America, let's see if we can get one of these experts to try them out on us!" Do this together, and you'll probably get some great tips that you can use, too.
You two might also have fun recreating some of the looks in a magazine with the clothes that are already in your closets. Or organize a clothes-swap party with other friends where you all bring items to trade, including bags and accessories. You can both practice make-up techniques with the cosmetics that are already in your drawers. Keeping current with fashion and trends doesn't have to cost a lot of money.
Keep in mind that ultimately, how your friend presents herself is up to her. It's not up to you, or anyone else. She might choose to stick with her current style, in which case, you and her other true friends will continue to love and appreciate her for who she is, and not judge her for what she wears.