I am either the best person in the world to shop with or the greatest nightmare because I believe in brutal honesty when shopping with a friend. I once told my mother-in-law to put back the coat she was pining after because it made her rear look ginormous. Yes, my mother-in-law. The words were no sooner off the tip of my tongue than I was looking for a safe place to hide. It shouldn’t have been a surprise that she appreciated my honesty. She would have blown too much money on something that didn’t make her look fabulous, and I have too much respect for her to have let that happen.

 

This is a tricky rule, because I’m not saying you should just walk up to a friend and say, “Hey, that outfit makes you look really frumpy.” That would be unkind and judgmental. However, if she asks for your honest opinion, feel free to offer a little hip help.

 

My friend Erica learned the hard way that I am honest when asked to be. She had this jumper, yes a jumper, which she loved to wear because it was unrestrictive and airy. After bearing four children, she’s entitled to dress comfortably, but a jumper? Often she would joke around with me about her jumper, and I would say, “Erica, no jumpers. You can do better.” So one day while I was at her house, she offered to show me the jumper. Oh that jumper needed to go by way of the highway and fast. It made her look like she was about to bear a fifth child. Did I mention that she is an avid runner with a killer body? You would never have guessed it was hiding under those mounds of fabric.

 

A couple of weeks later Erica called me and said she had thrown away the jumper. “What made you finally part with it?” I asked. It took nothing more than seeing another fashionably wayward woman in a similar jumper. “Frumpy and dumpy,” is what Erica said. I couldn’t have said it better myself. Knowing that Erica was interested in updating her wardrobe but unclear of what looked good on her, I offered to go shopping with her.

 

Yes, I was brutally honest. Yes, I stretched her to try on new things that would not normally have caught her eye. She didn’t spend a lot of money, she didn’t buy things that were not kid-friendly, and she feels great about herself because she knows that everything she bought that day looks great on her.

 

Don’t offer unsolicited advice (unless you have that kind of friendship), but if a friend asks, take the chance to be honest and inspire her to try new things that might help her feel more hip. After all, being hip is as much about attitude as it is about the right t-shirt, right? Most importantly, remember a hip mom doesn’t judge. She inspires. Take the time to put together your own hip outfit and you might inspire a friend or a stranger to get out of their own slump and work toward being more hip, too!