Two Day Magazine

Dear Natalie,

I love my girlfriend, but she is a terrible dresser. Every time we go out, she is either in sweatpants or clothes from the 90s and she looks ridiculous. She has a great body, but never shows it off and she just doesn’t dress like the professional business owner that she is. We are supposed to go to a big client dinner for my work in the next week or so and I am worried as to what she will wear to the event. Is there anyway to tell her that she looks bad and to get her new clothes without hurting her feelings? At this point, I would be willing to shell out a lot of money to buy her a new wardrobe.

--Wardrobe Malfunction

Dear Wardrobe Malfunction,

Yikes, I can see your dilemma. On the one hand, you don’t want to hurt her feelings or cause her to feel self-conscious about herself, but on the other hand, an important business dinner calls for playing the part of looking confident and put-together. If she shows up in a dated dress or “undone” it could reflect poorly on you. I know that’s a harsh thing to say, but the business world isn’t exactly warm, fuzzy and understanding. Appropriate attire required.

But, easier said than done. She may be dressing a certain way because of how she feels on the inside. Maybe she doesn’t feel great about herself or has a negative body image and it is being reflected in the way she dresses. So, be careful with what you say. The last thing you want to do is offend her. Or, who knows? She may think she is a great dresser and feel incredibly insulted by the idea that you don’t like her wardrobe. So, you may need to be a little sneaky.

*Normally, I don’t endorse sneakiness in relationships, but there are exceptions to every rule!*

You could go about this in two ways:

• Call up her best girlfriend or most stylish friend and ask her if he or she would do you a favor. Ask them to take your girlfriend out shopping and help her pick out some new clothes. Her friend may be a better avenue, as your girlfriend may feel more comfortable talking about her body image around her friend than around you.

• Offer to take your lady love on a shopping spree. Explain to her that you realize how hard she works and how little time she gets for herself and you just want to do something nice for her by surprising her with a new wardrobe. If she balks at this or says she doesn’t want new clothes, let her know that it’ll hurt your feelings if you can’t indulge her a little bit. (Yes, I’m breaking all kinds of rules! Guilt her into it!)

I know honesty is usually the best policy, but I worry that if you are honest with her about her closet, she may really get angry with you so speak softly and carry a big wallet.

Good luck and thanks for the question!

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