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Back to the Classroom – Work Outfits for Teachers

September 13, 2021

Hello! And welcome to Dressed for My Day. Recently when some of my readers shared their current or previous professions, we discovered that many are or were educators. And since I’ve received several requests for “teacher outfits,” I thought I’d provide some back to the classroom style inspiration today. These work outfits are perfect for teachers because they’re comfortable, functional and professional. But I’ll be wearing these styles this fall, too.

Back to the Classroom Work Outfits for TEACHERS and others

Now I’m not a teacher and I don’t play one of television either. But my mom was a classroom teacher for 30+ years. She always looked polished and professional, but she also generally opted for comfort and functionality, too. Of course the level of functionality you need from your work “uniform” depends largely on what and who you teach. So if you are in fact an educator, take from this post what works for you. And if you’re not an educator, I think you, like me, will enjoy the simplicity of these streamlined but polished outfits for fall.

I’ve created all of these outfits with just two pairs of pants and a simple dress. The pants are both pull-on knit pants with elasticized waist bands. They both have a slim fit with a slenderizing silhouette and a lot of built-in comfort. The first pair is from Everlane. The Dream Pants come in five colors (some of them are on back order) and sizes XXS to XL. I’m wearing a medium in the black.

Back to the Classroom black pants
The Dream Pants from Everlane run true to size.

I took the photos with my iPhone, so the quality of the photo does not do the pants justice. They are a nice, thick 58% Cotton, 38% Modal, 4% Elastane and you can wash them in the machine and then lay them flat to dry. I love these pants and I’m having to resist buying them in more colors. Let’s check out the outfits I created with them.

Back to the Classroom black stripe tee
black and white stripe snap cuff tee // Dream Pants // Sarah Flint Sachetto ballet flats // split hoop earrings // similar long pendant necklace

For this first outfit I simply topped the Dream Pants with a striped black and white stripe snap cuff tee. This is a soft, stretchy casual shirt, but it combines with these knit pants to create a polished outfit that is also easy to move in and uncomplicated. Use code SEPTEMBER at Evereve to receive 15% off this black and white stripe snap cuff tee and the rest of your order.

I’m wearing my Sarah Flint Sachetto ballet flats purposefully because they also are comfortable, chic and functional. Yes, they’re pricey. Use code SARAHFLINT-BAKAYH for $50 off your first purchase. But if you’d like to check out some more economical black flats, see the shopping widget below.

For the next outfit I simply topped the black Dream Pants with a classic white shirt. Did I mention that these Dream Pants have pockets???

Back to the Classroom white shirt
fitted stretch shirt // Dream Pants // Paul Green black patent loafers (similar) // split hoop earrings

This fitted stretch shirt is from Chico’s and it is made of 63% cotton, 33% polyester, 5% spandex. So it has a lot of stretch and feels really great on. I’m wearing a size 1, which is equivalent to a misses size 8. For this look I wore my Paul Green black patent loafers, also extremely comfortable but chic. Mine are basically sold out, but these are very similar and available in more sizes. Again, I’ll have more economical options in the shopping widget below, but I can highly recommend these modern loafers from Everlane. I have them in the camel and they’re great.

Back to the Classroom white shirt and vest
fitted stretch shirt // Dream Pants // Paul Green black patent loafers (similar) // split hoop earrings // button sweater shell

Then I added this soft beige button sweater shell from Ann Taylor. It’s marked down and they’re offering an additional 50% off in the checkout. This is a great little vest you can wear so many ways.

Next I created a slightly more sophisticated but equally comfortable look by topping the Dream Pants with a paisley mockneck sleeveless top and my camel peak lapel boyfriend blazer.

Back to the Classroom Paisley and Camel (1)
Dream Pants // Paisley Mockneck Shell // Sarah Flint Sachetto ballet flats // split hoop earrings // peak lapel boyfriend blazer

Again the paisley mockneck sleeveless top is silky comfortable. It has a zipper in the back and runs true to size. You could also wear this sleeveless top with other toppers, such as a black blazer, red coat, denim jacket or camel cardigan. If these are your colors, it’s quite versatile.

Back to the Classroom Paisley and Camel
Dream Pants // Paisley Mockneck Shell // Sarah Flint Sachetto ballet flats // split hoop earrings // peak lapel boyfriend blazer

A lot of readers picked up this peak lapel boyfriend blazer when it was 40% off recently. You can bet I’ll be styling it a lot this year.

Next I created outfits with these plaid ponte knit pull-on pants from Loft. They’re under $50 today with code LOFTIMIST. They are equally comfortable and oh so chic. I love, love, love these slim fitting but oh so forgiving pants. And yes! They have front pockets!

Back to the Classroom Grey V-Neck
plaid ponte knit pull-on pants // ribbed split neck top // Sarah Flint Sachetto ballet flats // split hoop earrings // Gorjana Venice necklace

I topped the plaid ponte knit pull-on pants with a ribbed split neck top I purchased in the Nordstrom Anniversary Sale. But the good news is that it’s still available in this grey, ivory and black in limited sizes. And it’s once again 40% off. This fairly lightweight long sleeve split neck top is functional but also a little more elevated than a plain tee. And it shows off my Gorjana Venice necklace beautifully.

But a simple v-neck t-shirt is exactly what I used in the next outfit with these plaid ponte knit pull-on pants. However, I will say that this Madewell v-neck t-shirt is a little thin for my taste, at least in a professional setting. So I would probably opt for L.L.Bean’s v-neck tee instead. I’ve ordered one in a medium.

Back to the Classroom tee and blazer
plaid ponte knit pull-on pants // luxe knit two-button blazer // v-neck t-shirt (another option) // Sarah Flint Sachetto ballet flats // split hoop earrings // Gorjana Venice necklace

But the idea is simply to top the plaid ponte knit pull-on pants with a simple white tee and a blazer. I’m wearing my luxe knit two-button blazer from Talbots, but I’m going to include the Everlane easy blazer in the shopping widget below because it’s a lower price point.

Next I topped the plaid ponte knit pull-on pants with a deep mahogany flecked sweater, also from Loft. I’m wearing a size medium in this very comfortable light to medium weight sweater.

Back to the Classroom Sweater for Fall
plaid ponte knit pull-on pants // flecked sweater // Sarah Flint Sachetto ballet flats // split hoop earrings // Gorjana Venice necklace // necklace no longer available

The outfit above would certainly be a little warm right now (unless your school is quite chilly!). But it’s a great option for later in the fall.

For my final outfit with the plaid ponte knit pull-on pants I envisioned taking the classroom outside for a beautiful day with this fun “Let’s go outside” graphic tee from Madewell. This graphic tee will sell out FAST! It’s just like the “Good Days” tee I wore this summer that so many readers admired. I’m wearing my true to size medium.

Back to the Classroom Let's Go Outside
plaid ponte knit pull-on pants // graphic tee // tailored jean jacket // Converse sneakers // split hoop earrings // Gorjana Venice necklace

I topped the graphic tee with my Talbots tailored jean jacket which has recently been restocked in a full range of sizes. It won’t appear in the shopping widget below, but you can check it out here. Unfortunately it’s not marked down right now, but it will sell fast when it is.

I completed this casual day work outfit with my Converse sneakers. I sized down .5 in these.

Back to the Classroom blue dress
Everlane Parklet Shirtdress // Ally Kitten Heels in caramel leather (use code KAYHEELS for $40 off your first pair of heels at Ally) // split hoop earrings // Gorjana Venice necklace

And finally, I wanted to share my new Everlane Parklet Shirtdress as an early fall option that you can pull out again in the spring. It’s still 15% off and available in most sizes. I’m wearing an 8.

I actually wore this outfit to church yesterday and opted for my Ally Kitten Heels in caramel leather (use code KAYHEELS for $40 off your first pair of heels at Ally). But this casual but beautifully made dress also looks nice with flats or even sneakers.

Which of these work outfits is your favorite?

Shop the Post:

You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

Thanks so much for stopping in today. And whether you’re a classroom teacher or not, I hope you got a little early fall style inspiration from my work outfits. Have a lovely day!

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Blessed for My Day

A gracious word can be such a gift to someone today. Think of the times when someone has some said that lifted your spirits, affirmed you, pushed you forward a little or calmed you down. Our words are powerful. They often have more impact in people’s lives than we first imagine.

Of course that’s why it is very important that we be careful with our words. They have equal if not more impact when they wound, discourage, squelch or hinder. In fact, for every disheartening thing we hear we often need half a dozen more gracious words spoken over us to get us back on our feet again. Why not make it your mission to give everyone you see some gracious words today?

A word fitly spoken
    is like apples of gold in a setting of silver. ~ Proverbs 25:11

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xoxo, Kay
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25 thoughts on “Back to the Classroom – Work Outfits for Teachers

  1. Do the Dream pants get all saggy in the knees? ? We call it elephant knees; where knees still look like you are sitting when you stand up!

    1. I know exactly what you mean! ?No, I’ve worn them and sat and walked in them for several hours and they did not. Now that’s with pretty normal wear. I guess if you were getting up and down from your knees a lot they might… but I really think the fabric is formulated not to do that. If you check the reviews you’ll see that they got a 4.46 rating out of 5 with over 240 reviews. Of course there are a few negative reviews. I read over those and think most of them could have been solved by sizing down. I’m wearing a medium so that’s my usual size. But the medium is supposed to fit sizes 6-8 so that would in fact almost be sizing down for me since I usually wear an 8.

  2. Good morning Kay! Your post struck a thread with me after 30 years in the classroom and finishing up working with new teachers. All your outfits are lovely and so appropriate. As a new teacher mentor, I sometimes struggled to have a conversation about clothing choices. While this could be generational, no one needs to reveal deep cleavage in the classroom – no matter the age of the students; unfortunately, this happened often. I’m hopeful that there are clothing and idea blogs out there for new teachers now that address this. Your BFMY was the topic of the sermon at church yesterday. So important! Your blogs have pulled me through a couple tough months! I’m here every morning reading you with my coffee! Keep ’em coming and have a great day!

  3. Kay,
    I’m wanting a pair of black slacks. I’m 5’8, but have a tummy. Do you think the dream pant would be a good choice? Thank-you ,Laurie

    1. I think so. They’re not especially dressy, but they can be dressed up – if that makes sense. So if you have a more casual lifestyle and just need some black pants you can occasionally dress up these would be great. You can wear your shirt out instead of tucked.

  4. Love your outfits. Taught 3rd grade for over 35 years. Teachers now are so much more casual than when I started out. I would say no blazers. Last year with COVID my friends said with lots of cleaning and outside mask breaks their dress was even more casual. I like you casual outfits that still look professional.

  5. Kay, I am currently taking an online training class for substitute teachers, so today’s post was particularly helpful. Thank you as always and happy belated birthday to your mom. I know that she influenced both you and your students well.

  6. I don’t see many vests on blogs but I like them. I’ve worn Catalina vests a lot. I haven’t bought any in a long time but I really like the color of this vest. Ponte pull on pants are great when you know you need something comfortable and I have them in basic colors. I don’t tuck them in but usually like a tee shirt, I wear a third layer when I wear them because of a bubble tummy.

  7. Thanks for the great looks that many of us can duplicate by shopping our closets! Love the plaid ponte slacks. I agree with comments that teacher attire has become very casual. I like that your looks are professional and don’t leave one guessing who the teacher is! A ‘young’ fellow teacher did a survey during his Masters classes about five years ago regarding how students equated a teacher’s dress to his/her effect and their respect. Results made him change from athletic wear to a dress shirt and tie…:)

    1. Oh my, yes! Enclothed cognition tells us that our attire plays a huge role both in how others perceive us as well as how we behave because of what we’re wearing. I’m all for dressing a little more casually than in the past, but I believe it’s important to elevate those looks by choosing the right fabrics, using the appropriate style hacks and accessorizing accordingly.

  8. Hi Kay,
    I just got the Loft pants and thanks for showing so many ways to wear it. I am really excited to try them all this fall ! Also probably a black cardigan option could also be added to that. 🙂

  9. My mother was also a teacher and then a principal at King Springs, Austell, Teasley, and a couple of other elementary schools in Cobb County whose names I can’t remember right now. She would have loved these classy looks!

  10. Kay, it is hard to say which outfit I like the best. Each is appropriate and classy and exactly the way I liked to dress for school. My favorite feature about all of the outfits is that they are stylish and each element mixes so well with the others. To quote you, “they play nicely together.” I like that this wardrobe is economical too.
    I agree with the reader who mentioned that many of the young ones in the teaching profession need to learn how to dress for the classroom. Personal style is individual and it can be a difficult subject to approach.
    Thank you for a great post. Proverbs 25:11 is a favorite of mine. Thanks for sharing it in the devotion.

  11. Kay, Those are great outfits, not only for teachers, but for the rest of us. I just ordered the Madewell graphic tee and became an insider to save on the shipping. I envision me wearing it a lot! I hope that you are having a great day.

      1. Thanks for the great teacher looks. I used to teach at a school where all the teachers dressed very well: in dresses, dress shirts with ties, etc. Then I moved to a small rural school district where the dress was very casual, and it didn’t always feel very professional. I have tried to find a middle ground, so I am professional, but also casual. Your outfits fit my middle ground well, so they are a great inspiration. Thanks for a great post.

  12. I like all of your outfits. I really like the look with the vest. As a teacher with no air conditioning, I am actually looking forward to cool weather so I can wear some outfits like that. It was 82 degrees today in my classroom, so I’m still wearing sleeveless dresses and sandals most days. Of course, I could need those outfits by next week. You never know in northern Ohio. 🙂 Have a blessed day!

  13. Thank you for this useful post. I teach high school, and I like to look presentable. Most teacher outfit ideas online feature short skirts, etc., but you are spot on with these outfits. Loved everything here!