How to Save the Unfashionable Friend

By Kelly Hockenberry, Columnist,

We all have one….the girlfriend who you are dying to make-over!  Bring her to the light, so to speak. But, HOW? How do you do that without hurting her feelings? If you are fortunate enough to know me personally (ha!), you know that I have very little problem expressing myself. And, I have been known, on occasion, to be somewhat obnoxious about it. Gasp!

However, this is my attempt at being NICE, being helpful but somewhat sneaky and underhanded at the same time.

Let’s set the scene, shall we?

Girlfriend #1 is “Molly Martyr”. You know her, the one who proclaims to “not have enough time to worry about her appearance.” Hence, the two inch roots, jeans from 1987, her husband’s sweatshirt and the dreaded white sneaker.  How can you help?  I find that with women like this, you need to approach them like you would a small, timid animal. You don’t want to scare them with couture or bombard them with too trendy items.

I suggest a “Mom’s Day Out” where you, just perhaps, make a pit stop for some shopping on your way to lunch and a movie.  While you are IN the store, casually offer to pick out an outfit that she should try on “just to see how it looks.” When she comes out of the dressing room looking like the MILLION dollar version of herself, go CRAZY with the compliments!

Be careful to use your “indoor voice” though….that’s what she is used to. Remember, this particular girlfriend will struggle with actually spending her money on something that doesn’t directly involve her children. Assure her that her daughter will be able to borrow her fabulous jeans in six to ten years when she’s old enough.

Girlfriend #2 we’ll call “Franny Floozy.” She has enough cleavage to make Dolly Parton jealous and doesn’t mind showing it to the world. And may I add that, I am in NO way bitter about this. My Hillary Duff Collection Bras are available at WalMart and come in a variety of colors! But, I digress. Franny’s skirts are too short, her pants too tight. She actually buys clothing to reveal the large butterfly tattoo stamped on her lower back. She has a tendency to over-accessorize: a ring on every finger (including the thumb which is a Kelly Hockenberry proclaimed NO NO), dangerously spiked heels and the dreaded ankle bracelet. Her make-up is harsh, her eyebrows penciled in an angry line and her hair is probably a shade not found in nature.

How to help? Hmmmm, this one is tough because chances are she can kick your butt. Tread softly. But, she’s different from Molly Martyr. She WANTS people to look at her! I suggest a JCrew gift card for her birthday (which you will have to forcibly ensure is used) or maybe a subscription to Vogue or Lucky magazine. Take the time to earmark outfits that you think she should try.

Suggest going to the make-up counter at the mall and ask for a mini make-over. Request that the two of you get a “natural daytime look.” Then, just like with Molly, kill her with kindness! Everybody loves feeling pretty!

Girlfriend #3 is “Cathy Crunchie”. She is usually serenely decked out in her broomstick skirt, a mismatched t-shirt (sans undergarments) and a pair of Birkenstocks or Crocs (which are equally as hideous). She may still be wearing the earring in her nose or eyebrow that she got in college. Ouch.

Cathy’s hair is washed a few times a week and is reminiscent of Crystal Gail.

How to help?  I think that this may call for some “tough love”.  Take her to Starbucks, get her a grande chai latte and tell her that her days of following the Grateful Dead have been over for YEARS. Tell her that you’ve booked a hair appointment and accidentally (on purpose) spill the remainder of your coffee on her multi-colored hemp woven cross-body satchel.

Remind her that even Drew Barrymore gets it right every once in a while. You can be left of center and still look cute. There are many organic based clothing lines and vegan shoes to satisfy her need to be “alternative” and “eco-friendly” without appearing homeless or like an extra from The Partridge Family.

Have I helped? I don’t know. The unfashionable friend is a tricky one. But, fellow fashionistas, it is our DUTY to beautify our surroundings.  Until next week….

DISCLAIMER: The names of my “girlfriends” have been changed to protect the innocent. You know who you are.

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  1. VR says:

    Hey Kelly – this column is brilliant! So sassy, and so well put.
    I love it. (It also helps me to look at myself from the outside, as it were!)

  2. Emma says:

    In the spirit of March Madness, I will offer a basketball analogy. If the 10 “Must Haves” of your first list were free throws, I would be 1 for 10. I don’t have the perfect jeans (and anyone who has time to try on 100 pairs needs to get a job or a life), my black blazer is not “tailored,” the only watch I own is a sports watch, my charcoal gray wool coat hits mid-shin, and I wouldn’t wear anything animal print (even with a gun held to my head).
    If I had to align myself with one of your current characters, I would choose Molly Martyr. I don’t dye my hair, have jeans from 1987, or wear my husband’s sweatshirt. However, I don’t enjoy shopping or spending money on myself. I might go out once in the winter and once in the spring to freshen up my wardrobe, but I tend to buy classic styles that I can wear for more than a season or two. This contributes to a significantly lower “price per wear” as you mentioned. If you were to meet me you would probably want to make me over with the latest trends, but some people are not looking to be saved. If you want to beautify your surroundings, go plant some flowers. Game over!

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