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Teachers have it tougher than most when it comes to getting dressed for work, so we picked the brains of some stylish schoolteachers for their tips. Click through for nine common quandaries of classroom style—plus outfit ideas to help make back-to-school season a breeze.
Staying true to your style—within the bounds of a dress code

"My new school is very particular about what we can and cannot wear. They tell us that when we get dressed for work, we should wear what we would wear if we were a businessperson or a lawyer—if it wouldn't fly at a law firm, don't wear it. The thought process behind that is that we should be modeling for our students what a professional looks like. Also, we want them to know that they are worth making an effort to look nice for. I love this mindset, especially because I work with students who typically do not have this kind of model at home.

For the record, though, I don't think I will ever look like a lawyer. I scream 'teacher.' I wear lots of bright colors, but I do look professional!" - Lauren, a fifth grade teacher in Missouri

Keeping covered up—and still dressed up
"Tank tops under everything" is a common refrain across the board, especially when wearing button-ups or anything that might read as even a smidge too low in front of parents. Bike shorts or compression shorts also offer extra coverage under dresses ("middle school boys!"), and footie socks keep flats fresh even after a long day of standing.
Choosing the right shoes

"It’s hard to find shoes that are stylish for a 20-something, but have 'arch support' and all the other requirements our parents/grandparents discuss very openly about their footwear. As comfortable as Aerosoles may be, I refuse to wear shoes that are 'old lady.' I’d rather suffer.

I’m a big fan of the Minnetonka moccasins, Bass loafers and my Madewell ankle boots." - Erin, a sixth grade teacher in New Jersey

Knowing what's age-appropriate

"I try to dress as 'adult' as possible, especially since my students are almost my age. It was less of a hassle as a TA, but now that I have my own class I dress way differently. No short skirts or shorts, nothing that shows my shoulders, usually no jeans unless they're really dark denim and nothing sheer ever. I always wear 'adult' shoes—my favorites are the ones that make clacking noises—and try to hide my tattoos and piercings, forgo sparkles and lipstick and wear a layering piece so I look amorphous.

I also tend to dress more conservatively in general—running into students at the grocery store when I'm in an American Apparel bodysuit or something is embarrassing as hell." - Helene, an assistant instructor at a college in Texas

Finding the balance between comfortable and professional
"I work with kids at a before/after school program ranging from K-5 grade. Since half my job is leading group games, I tend to wear jeans and a nice shirt. I also wear flat shoes (in case I have to chase after a runaway kid, lead a game of tag, etc.). I always struggle with low-cut tops though. How low is too low? I hate wearing tank tops underneath, but sometimes I feel like I have to. I see parents on a daily basis, so I feel it's important that I look nice, but also like I am approachable and flexible." - Miriam, a school site director in New Hampshire
Finding a grown-up tote big enough to stash papers
Hauling around student essays on Moby Dick (not to mention the tome itself) presents a certain set of challenges. Canvas totes are practical, but having one bag that's nice enough for parent-teacher interviews—or Friday happy hour—is always a good bet.
Finding height-appropriate outfits

"Last year was my first year teaching sixth grade after coming from second grade. I found that I have been much more conscious about how I dress with this age. I am much more aware of skirt and dress lengths, and since I am tall and have long legs, this makes shopping for work difficult.

I think that I own every single striped Ralph Lauren dress from Lord and Taylor. I find them easy to throw on with tights and boots, flats or heels. Pencil skirts with blouses are also my go-to. J.Crew and Ann Taylor Loft have great ones—they also do discounts for teachers!

All of my colleagues live in heels but since I am so tall, I don't wear them as often. If you walk into any of our classrooms, though, we all have a pair of heels hidden under our desks so we can switch out of flats just in case the superintendent comes in (it happens quite often!)." - Logan, a sixth grade teacher in Massachusetts

Dealing with disrespectful students

Ok, this one is (somewhat) in jest, but apparently it's effective!

"One semester, my students were extra rowdy, so I specifically tried to dress like Meryl Streep in the movie Doubt. It worked! They feared me!" - Helene, an assistant instructor at a college in Texas