30+ Teacher Workwear Looks for Back to School

10 August |

DRESS | SHOES | BACKPACK

It’s that time of year again, back to school! Last year, I featured over 30 teacher workwear outfits for back to school in this post. You all loved it so much that I decided to make it a yearly tradition. This year, I’m curating a two-part blog series that will total over 50 teacher workwear looks. Today is part one of two, featuring workwear looks that are perfect for teachers or an office setting!

When I first started Loverly Grey, the heart of my brand was sharing my daily work outfits. I was in a professional office setting that required me to dress up daily. So I took this as a personal challenge to create outfits that were professional, stylish and gave me confidence. I love that six years later, I still get to share my favorite workwear looks. I can’t wait to hear which one is your favorite!

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You can never go wrong with a midi dress! This one features a fun cut-out back. I layered a denim jacket over the top to make it a little more classroom friendly. However, this would be great option if you have plans after work. Swap out the sneakers for heels, and you’re ready for a dinner date with friends.

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When styling a peplum top with a lot of volume like this one, I like to create balance by pairing it with a more fitted bottom. The cropped tailored pants on the left draw your eye upwards, while the cropped flare pants on the right create a balance that is easy on the eyes. Both looks are perfect for a business casual setting.

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One of my favorite workwear pieces is a shift dress. This light pink dress from Old Navy has a sweet eyelet sleeve detail that gives it just enough personality, without being too trendy that you won’t want to wear it in a year. I paired it with suede booties to give it a fall look. This is a great way to start transitioning into fall while it’s still warm outside.

30+ Teacher Workwear Looks

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If you’re on the hunt for a workwear piece that is equally comfortable and cute, look no further! This midi dress is extremely flattering and has the perfect amount of stretch. On a chilly fall day, layer a mauve waffle cardigan over the top and pair it with a mauve handbag. This $40 Target work tote has three compartments. The straps are long enough to get your arm under it comfortably, and it’s lightweight.

30+ Teacher Workwear Looks

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A maxi dress is a wardrobe staple that can easily go from work to weekend. This dotted-print, flutter-sleeve maxi dress is an Amazon find. It comes in seven other colors and is $32. I styled it with my favorite braided heels and Target tote bag. This tote bag comes in eight other colors and is $30. It features an interior pocket, a tablet pocket and a large zipper pocket. The lightweight design and soft vegan leather makes it an ideal choice for toting things back and forth between work and home.

30+ Teacher Workwear Looks

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Another teacher wardrobe staple is a denim dress. I consider it to be a piece that you can truly wear all year. Pair it with knee-high suede boots and a cream tote bag for a look that you can wear now. If you’re going to be on your feet all day, opt to style the denim dress with a cardigan and leopard flats. My leopard Rothy’s are an investment piece that are well worth the price. They are by far my most comfortable flats. The coolest part, they are made of single-use plastic water bottles! They are the perfect example of sustainability and fashion colliding.

30+ Teacher Workwear Looks

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Another closet staple piece is a denim jacket. I’ve had this one for years. I love the medium to light wash. I styled it with a $12 t-shirt dress and sneakers for a more casual look. This would also be a great option if you’re working from home or doing virtual teaching!

I found this lanyard on Amazon, and it comes in multiple colors. This would make a great teacher gift for back to school or for teacher appreciation. Tuck a Starbucks or Target gift card into the clear sleeve for a fun surprise.

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This floral print midi dress is another great fall workwear find. It features a split neck and puff sleeve detail. It also has pockets! I styled it for a professional setting on the left and more casually in the look on the right. By swapping the pointed toe flats and cream tote bag for sneakers and a denim jacket, this dress can easily go from workweek into the weekend! If you’re a UGA fan, this floral print midi dress can also double as a gameday dress! The bold red color is perfect for attending a game or watching it from the comfort of your home.

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When thinking about workwear pieces that you can wear to work and beyond, this midi dress is a must-have. I love the floral print and the fall color palette. I styled it with my favorite suede flats that I picked up last year. These also come in a mule option, as well as other colors!

30+ Teacher Workwear Looks

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If you’re in need of a business professional look, I’ve got you covered! Both of these are classic workwear looks for those important presentations or meetings that you may have pop up throughout the school year. In the look on the left, I layered a classic black blazer over the top of a neutral midi dress and rounded out the look with loafers. In the look on the right, I layered a v-neck sweater vest over the top to give the illusion of a top and a skirt. Add an animal printed belt and pointed toe heels to complete the look.

30+ Teacher Workwear Looks

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This leopard print midi dress has quickly become a favorite of mine. I love the layered look of knee-high suede boots under a dress in the fall and winter. It’s an easy way to look elevated by wearing a dress, but still be seasonally appropriate. As we move into the winter months, layer a blazer over the top for an added layer of warmth.

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This $40 pink dress from Old Navy is extremely versatile. Here I kept it simple by layering a cocoon cardigan over the top and pairing it with suede knee-high Sam Edelman boots that I picked up during the Nordstrom Anniversary Sale. To see it styled six more ways, check out my recent reel here!

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There are so many ways you can style a floral printed midi dress! In these three looks, I’m showing you the power of layers. With the first look on the left, I’m keeping it classic with a pointed toe flat and a cream handbag. In the middle look, I’m going for a more casual vibe. I layered a henley tee shirt over the top and added a light-wash denim jacket. The sneakers give it an overall more relaxed feel. The final look on the left features a white button down with a cream sweater vest over the top and a skinny black belt to pull the look together. The varying shades of white in the sweater vest and the button down provide depth and dimension.

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In these next few looks, I’m showing you how to mix and match pieces with items you likely already have in your wardrobe. Take this layered set on top and pair it with classic black pants. I love the pop that the leopard print flats give to this neutral look.

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Another option is to pair the cropped flare black pants from above and swap the sweater set for a striped tee and structured black blazer. These pants were on the top best sellers for the entire year of 2021 for good reason! They have the perfect amount of stretch to them, yet they offer great support and structure. They are also an affordable price point at just $29! I recommend sizing up one from your normal size.

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These high-waisted paper bag pants have been a favorite of mine for years now. If you’ve been following along, you’ve likely seen these styled many ways over the years. I love them so much that I own them in multiple colors. I love that you can style them multiple ways and easily dress them up or down. Continue scrolling to see these pants styled three more ways!

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If you’re wanting to add a fun pop of color to your work wardrobe, these pants are a great option! I paired them with two neutral tops for on-trend workwear looks that are both cute and comfortable.

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To show you how to stretch your wardrobe even further, I’m bringing you multiple ways to style a neutral sweater! Take the same henley sweater from above and swap out the $30 high-waisted Amazon pants for wide-leg black pants and flats. This gives you another workwear option that you can wear now and throughout fall!

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I couldn’t coordinate 30+ teacher workwear looks for back to school and not include a few looks that feature a work wardrobe staple item, the black pencil skirt. This was one of my most worn pieces when I was working my corporate job. I love that you can pair it with heels and a cardigan or a classic white top and flats.

I’m excited to see all the variations you create from this outfit inspiration post! Feel free to bookmark it and come back on those mornings when you’re standing in your closet wondering what to wear to work.

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Which of these 30+ teacher workwear looks for back to school is your favorite?

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  1. Thank you so much for putting these ideas together! It really helps me extend my wardrobe for every day in the classroom when I look at your stylings!

  2. I love ALLthese teacher looks. I have gained a lot of ideas and inspiration as I head back to school. I appreciate your wide range of stores and prices of the items you select and share. 🙂

  3. I love them all; but especially the cream sweater vest(ish) over the white blouse. You have totally pulled off the “teacher look” 🙂

  4. These outfit ideas are so helpful for all educators, including school psychologists like myself. Thank you for the inspiration!

  5. I teach second grade and I have my first interview for an assistant principal position tomorrow! I’m so excited to get inspired for a look to wear to the interview!