A sad, sad story from my pathetic fashion life…

“May I help you?” asked the saleswoman.

“Yes. Yes, you can.” I said. “I ate too much recently and gained a pants size, maybe more, and none of my clothes fit. I got new jeans but I forgot about school clothes…” I had to get sympathy from her because my coworkers told me to shut up, that everyone’s always trying to lose weight and I was not getting fat.

She heard the panic in my voice and alarm bells in my wallet. I hate clothes shopping. New clothes are never comfortable. They’re always impractical and feel different. I need comfort. I’m active. I hate squeezing, pinching, wedge-giving new cuts of clothes.

You won’t catch me dead in teacher dresses and heels either, freezing my butt off walking around in pain.  Besides, I can never predict the temperature at school–it can go from ninety-five to zero in no time flat and it’ll stay that way indefinitely.

Getting school clothes right is a delicate balance involving performance techwear, comfort, and practical hiker-grade layering skill. Oh yeah–and they have to be stain resistant. Just spray me down with Scotchguard and send me through the door.

School was in two weeks, and the more I went running, the more weight I gained.

“Mom, you should buy some pants that are friends with your thighs,” said my nine-year old boy, trying to help.

There was no doubt about it, I needed to go shopping immediately so I could get to the tailor in time. I can’t always buy clothes off the rack–I’m taller than “petite” and shorter than “regular.” Every designer in the world mocks me, if not with price tags, then with fit.

Nice clothes aren’t designed for schools where kids vomit and dustballs attack slacks. Experienced teachers know this.

I’m finally old enough that I have experience. I understand the teacher who’s still wearing the 70’s dress pants or the 80’s pleated slacks. I used to judge. I’d think, “Get with the decade at least,” but now I high-five them. They’re my heroes. Everyone else is running around paying top-dollar for vintage and they’re already in style.

“Nice platform shoes, dude.” I saw those on a website for a few hundred dollars. And that vest–it’s a classic.

The real reason teachers wear clothes for centuries isn’t fashion, it’s that school ruins clothes.

No one wants to pay for John Varvatos and Prada when it’s only going to get destroyed the first week. That’s like wearing Versace to mow the lawn–someone might question your intelligence on that one. Even though no one questions anyone’s intelligence in education, I’m still too cheap to crack open my wallet for an entire new wardrobe. That’s downright frightening.

But that’s what I had to do, and the saleswoman was waiting.

“I thought shopping might be easier than buying a whalebone corset and hiring a handmaid to help me dress every day.”

“What do you like?” she asked.

“I like my clothes to fit and be comfortable.” Beyond that, everything else was fair game.

She found me a dressing room and brought me a hundred outfits. I felt sorry for her. She was holding an armful of “no’s.”

“No…these feel like church lady pants.”

“No, these give me a wedge…”

There had been one cut of pants I loved–the one I just grew out of. No amount of lettuce was going to resurrect them for this school year.

She nodded and brought me pants with the same label, one size up, but they were not the same. The bottom wasn’t straight–it was a peg leg designed for torture shoes. I might be buying a whole new wardrobe, but I’d never give in to fancy shoes.

“Can I wear boots with these?” I knew the answer in my heart.

“No,” she said. “You need heels or ballet shoes.”

We argued about the plausibility of hiking boots, which she rejected. I bought the pants anyway. I’ll figure it out later.

For years, I wore the same few outfits to school every day–three pairs of Dockers and four or five golf shirts stolen from the business casual playbook at my prior corporate job. I saved a lot of money but no one was very amused by my “school uniform.” These days wearing the same two or three outfits is highly respected as “minimalist” and “zero waste.” The cool kids avoid shopping by saying they’re saving the earth.

I think that’s pretty nifty.

These days I’m a little better at fashion–I buy the same things over and over when the 40% coupon comes out. I want to put the same clothes on reorder, but designers insist on choosing new cuts, colors and “seasonal styles.”  I hate that.

Thanks to modern technology, I can find styles untouched by time in other fashionista’s closets in designer repurposing shops like ThredUp and Poshmark. One girl’s wedge is another girl’s treasure. You can even sell your “I thought I’d like those but they gave me a wedge,” clothing you’ve been sitting on long enough to call them “vintage,” and get top dollar.

Now that my one-size bigger wardrobe is complete, all that extra weight’s flying off as if it knew I just hung the last, larger, pair of pants in my closet.

Dammit, I want to wear those clothes, but they’re a little too big now.

So, I bought and ate a Labor Day cake and everything still fits. Now that I discovered online thrifting, I can eat a second cake and know that I can get a one-size-up wardrobe with the touch of an app.

And so my shopping is done, with much less stress than normal.

The saleslady is going to heaven, and I got to have my cake and eat it too.

That’s a win-win.

Let the school year begin…


Yes, it’s time for a new book! I’m just finishing up the edits to “A Broke Teacher’s Guide to Success.” Stay tuned!  Check out the BrokeTeacher project at BrokeTeacher.com for tips and tricks for living like royalty on teacher pay & join the BrokeTeacher newsletter to be the first to know about the release. 

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