Dressed for Success?

Well school has officially kicked off, and once again I am confronted with a question that I have been repressing for the past three months. It haunts me once again every night as I drift off to sleep; it roars its ugly head every morning in the darkness of the early hours as I stare bleary-eyed into my closet. Upon this question my professional success rests: What should I wear today?

I am 24 years old, and my co-workers are predominately middle-aged women (30-40 years old, all with children). I had originally assumed that I could stay ahead of the fashion curve among this particular peer group merely by virtue of wearing pants and skirts that are not elastic-waist. While that might be true in other elementary school settings, it doesn’t work at my school. These women have set the bar high; therefore my daily work attire conundrum is multifaceted:

Trendy vs. Professional: I am trying to compete as an equal among women who tend to view me as a daughter. Therefore, I try to dress in a way that is classy and mature yet which does not look like I’m trying on my mother’s clothes (BTW, this is really not a great comparison, as my mom is a pretty hip dresser. But you know what I mean). I find it quite difficult to walk the line between looking like I got lost on my way to class at Baylor and slinking around school feeling frumpy because I’m wearing a jacket with shoulder pads.

“Skanky Ho” vs. “Grandma’s Vest”: I thought that department stores would be the best place to look for clothing items that might be flattering yet timeless. It was really not even worth the trip. I first went to the “Petite” section, hoping to find adult clothes that would fit. This doesn’t work because you have to have all the right proportions, and my arms and legs are too long. So then I tried the “Ladies” section, where I was immediately repelled by the price of the items for sale as well as the abundance of clothing featuring sequins and appliques. So, hoping I would not see anyone I knew, I sneaked back to the “Juniors” section. After navigating past the string bikinis and “Mrs. Federline” baby tees, I found the dressy clothes. I even got as far as trying some of them on. But everything was see-through and/or cropped and/or low cut and/or bell-bottomed and/or decorated with cherries. Thanks, but no thanks, Dillards!

Affordability vs. Respectability: The clothes that I admire on my chic co-workers come from Ann Taylor, Talbots, and Chicos. Have you ever walked around in those stores? I can’t even get service. You can easily drop eighty bucks on a shirt. When it’s on clearance. My friend Katie has a knack for finding fabulous things at AT Loft for less than twenty dollars; I have never had that kind of luck. Rather, I find myself returning clothing items to the GAP outlet because I couldn’t sleep the night after I spent eighteen dollars on one shirt. How can I compete?

Seasonally Appropriate vs. Non-Frostbitten: I don’t like looking like the resident grizzly bear in my long sleeved, dark clothing among the flirty skirts and sandals of my more summery-dressed colleagues, but it’s frigid inside our building. I wore a long sleeved t-shirt today and my teeth were still chattering before class began. To keep my feet warm requires closed-toed shoes. Closed-toed shoes require long pants. My long pants are brown and dark gray. What to do?

Professional-tastic vs. Realistic: Yesterday I wanted to convey a “get down to business” attitude to my summer-brain-drained students, so I wore a button-down shirt with a straight wool skirt (from Ann Taylor–thanks, Mom!) and some really cute brown low-heeled pumps. I commanded respect all the way down the hallway and to the front of my classroom, where I immediately lost face by having to remove said pumps from my feet. By the end of the day, I was literally hobbling. Last Friday, I wore a pair of nice linen pants to school, and by recess they were spattered by student vomit.

Meanwhile, my husband tries to empathize with me by sharing his own wardrobe dilemma: which color mesh polo should he wear with his khakis today?

Life is not fair.

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9 responses to “Dressed for Success?

  1. what a sad life you live, dear lindsey. just think of how hard you have it…i mean, just think, at least you don’t have to go around starving like those lucky africans.

  2. ouch to the above!

    really, the post is right on. I’m in my 50’s and considered the best dresser on my campus simply because I change earrings every day. sheesh!

    After it’s all boiled down, forget the peer pressure and dress for comfortable professionalism. No more heels, but cute flats or mules. No dry-clean fabrics (re student vomit) but washable ones. Keep a classic sweater in the closet for those frigid room days (black or white) which will go with everything.

    Real Simple had a sample wardrobe this month: khaki pants, black pants, brown pants; white button shirt; white tees (long and short sleeved); black tees (long and short sleeved); a classic jacket, classic flats, black skirt. And, of course, the perfect “little black dress.”

    That would work in a professional office, but teachers wear those cute seasonal/holiday things! Well get earrings for every holiday (Penney’s is good for that) and forget the sequined Halloween vests and furry Christmas jackets. Been there, done that … hate the pictures! 🙂

    Good luck with choosing your clothes today!

  3. @Laura: Ah, the love of a sister.

    @Caroyln: I have all those Real Simple “staples.” I can never figure out how to look as cute as they do in the magazine, though.

    My dressing dilemma? Bank shirt vs. suit. Lately, the bank shirt has won since it is too hot to wear a suit. Sometimes it’s nice to not have to think about what to wear. Other times, I’d just like to wear my OWN clothes for a change instead of being a walking logo.

  4. Don’t listen to a word that Laurashmaura says. She sounds liek she has such perspective…yet she complained to me just the other day about the fact that she was so bored she had to watch TLC (ahem, that’s CABLE) all day in her new apartment. WHATEVER!

  5. You guys crack me up…

    I have found that some Targets, not all, have a great professional section. It’s trendy, but still professional, and easy on the wallet. I rarely find a must-have piece priced above $22.

  6. So true! Especially when half my clothes are in a storage unit and I can never remember what is in there! And I struggle between trying to look nice to command respect, but not wanting to look trendy or “rich” so my kids think I am a snob. what to do.. more commenting when I have internet at home.

  7. Well… I come into this conversation tentatively, knowing that I don’t have nearly the struggles most of you have, simply because of my work situation.

    In reality, I do have to choose from the closet twice a week–once for church, and once for my day in Waco. (I know, it’s so hard.)

    Because I’m a slacker all the rest of the week, I try to pay pennance by wearing really painful shoes to Waco. I dress in my cutest business attire, grab a pair of heels and some band-aids, and I’m good to go!

    By the end of the day, I can’t wait to kick off my shoes, take off the fab jewelry that has become quite annoying by the end of the day, and don my familiar uniform of shorts and a t-shirt. I fight foot cramps the next day from the heels, my face feels gross from the makeup, and my hair needs an extra washing to get rid of the hairspray, but I don’t mind.

    After all, I realize I’ve got the best of both worlds. I get to dress really cute and go all out a couple times a week, and the rest of the week, wear what I want…or nothing at all!! Hahahaha! 🙂

  8. I’m not laughing.

  9. You’re right. I was a little exultant in my previous comment. As pennance, I’ll do two Hail Marys and fix my hair today, with extra hair spray.

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