Tuesday Top 5: Style Lessons Learned in Colleen's Closet

My friend and coworker Colleen is awesome. She always has a smile on her face (even at 6 in the morning, when the most I can manage is an awkward grimace), she calls me Winnie, and she knows the lyrics to seemingly every song ever written.

Colleen is also severely fashion-phobic. When she found out about my book, she asked if I'd be interested in coming over to help her sort through her closet. "Sure!" I said. When she mentioned she would be inviting some friends over and making a cheese platter for the event, I said, "Can we do it right now?" (We settled for Thursday.)


When I got to Colleen's house I found out that after a recent life upheaval, her friends and acquaintances had given her bags and bags of clothes to help her build a new wardrobe, to help her build a new life. While this was a very generous gesture, she now had a closet full of beautiful pieces that didn't fit her, weren't her style, or that she simply felt no connection to.

We spent a few hours going through every item of clothing and deciding whether it would stay, be donated to a women's shelter, or sold at a consignment shop. I took mental notes throughout the night so I could blog about the experience (with Colleen's permission, of course), and here are a few lessons I learned:

1. It is better to have 10 things you love than 100 things you don't care about.

This is always a hard lesson for me to take to heart, as I am the kind of person who watches an episode of "Hoarders" and feels nothing but empathy and confusion--"Wait, what's so wrong with having 14 broken vacuum cleaners piled in your living room, on top of another pile of old magazines and medical waste? My living room looks a lot like that. I don't understand the issue here."

But seeing Colleen's clothing collection slowly shrink from massive to manageable, and watching her get more confident and less overwhelmed, was downright inspiring. You know that phrase "a full closet and nothing to wear?" A lot of times we have nothing to wear because we have an overflowing closet. Paring down your wardrobe--whether that means getting rid of a couple things that don't fit anymore or leasing a dumptruck to haul away two tons of old clothes--is always a good thing.

2. You get to define what you love.

Makeover TV show hosts are harsh and unrelenting in their quest to dispose of clothing that breaks fashion rules. In fact, they seem to most enjoy their jobs when their makeover subject is sobbing and pleading to keep a gnarly old college sweatshirt, and the host gets to ignore the earnest pleas, pry the beloved sweatshirt out of the subject's grip, throw it into a garbage can, and set it on fire.

There were a few times during Colleen's wardrobe makeover when she sheepishly pulled something out of the closet and began murmuring excuses, like, "I know this one probably breaks all the rules, but I really love it and it's so comfy."

In these instances I would say, "Colleen, do you really love it?" Sometimes she would think about it and say no, but whenever the answer to that question was yes, I'd say, "Then keep it! Duh."

So much of fashion is a visceral, emotional reaction. If you simply adore a piece of clothing, if wearing it makes you happy, then you shouldn't have to justify that with style rules and figure flattery equations.

3. You also get to define what you hate.

Colleen has a great figure, so a lot of clothes look good on her. There were multiple times during the evening when she would slip on a blazer or a dress and we would all gasp with amazement at how fabulous she looked. But if she looked in the mirror and obviously didn't feel the same way--her shoulders slouched or she tugged at the hem or she simply shrugged and said, "I don't think I would wear this--then it didn't matter what we thought.

Every woman of every shape and size can find a thousand things that look good on her--treasure the pieces that make you feel good, too. If you know that something isn't right for you, lose it. Throw it in a garbage can and set it on fire, if you want. Stepping out of your comfort zone is good. Feeling uncomfortable in your clothes is not.

4. Shoes are the anchor of your wardrobe.

By the end of the night we had come up with some rad outfit combinations. The problem remaining? The lack of a great, versatile shoe to pull everything together. I left Colleen with some fashion homework: find a pair of comfy, flat black shoes to wear with the jeans, trousers, and casual skirts in her wardrobe that are currently without a footwear partner.

5. While solo style introspection is important, don't underestimate the power of a brutally honest friend.

In this case that friend was Jill, who sat cross-legged toward the back of the room yelling "Death! Death!" whenever Colleen donned an unflattering shade of yellow.

When Colleen put on a particularly ruffly confection of a blouse, I mentioned that she sort of resembled a cake. Jill quickly took to bellowing, "Deaaaattthh caaaaake!" or chanting, "Yellow death cake! Yellow death cake!" Her criticisms might not have totally made sense, but somehow I always agreed with her.

p.s. Speaking of cake, one of my favorite blogs, The Big Piece of Cake, is giving away a signed copy of Closet Confidential! Please check it out!