Back to School: No-Fail Teacher Outfit Ideas from 7 Stylish Teachers

teacher outfit ideas for back to school

It’s go time, teachers! Kicking off the school year usually involves making lots of first impressions, not just with your students, but with parents, staff, and administration as well. Studies show that first impressions are formed within the first 17 seconds of meeting someone new, and a good first impression can help set the tone for positive relationships. A big part of that first impression involves what people see, so take some time to choose a teacher outfit that sends a positive message. Need some ideas? We’ve got you covered! I have teamed up with seven super-stylish, amazing teachers to bring you some examples of outfits that are perfect for teachers heading back to school.


I’ve posted my own teacher outfit ideas for  back to school night, the first day of school, and a casual school day below, and for even more inspiration, be sure to check out each of my teacher-blogger friends’ back to school ideas which are linked below below as well.

Note: This post contains affiliate links. Purchasing through these links may result in my earning a commission or referral fee at no cost to you. I truly appreciate your support of Everyday Teacher Style. As always, all opinions expressed here are 100% my own, and I always recommend brands and products that I have had good experiences with and think you’ll love, too.

Stitch Fix Find Your Style

Back to School Teacher Outfit Ideas

One Great Piece for Back to School and Beyond

Let’s face it: teacher salaries prohibit most of us from buying new expensive outfits at the drop of a hat. But luckily, with some basic closet staples, you can add a statement piece or two and create a whole new look. I found this gorgeous long floral kimono at Target recently (under $30!), and the colors are perfect for summer right on through late fall. Plus, it can be dressed up or down, making it an ideal addition to your back to school collection. I’ve styled this kimono three ways using other pieces I already owned so you can see how I plan to work it in as I head back to school this year.


Back to School / Meet the Teacher / Open House Night

Whatever you want to call it, most schools have an evening when parents are invited to their child’s classroom to meet the teacher and see the learning space. At my school, this takes place the evening before the kids come for their first day of school, so it truly is the first impression we make with both students and parents. Most of the teachers I know dress up a little more than usual for back to school night. The goal is to look professional (communicates “I know what I’m doing”), polished (communicates “I’m organized and responsible”), and stylish (communicates “I’m current with the times”). I love wearing a dress or skirt on open house night, but there have been a few years when I’ve chosen to wear pants as well. A pretty kimono can dress up an otherwise plain outfit while still keeping you comfortable and cool (duh, August).

Kimono with dress

Shop This Look:

Back to school night kimono


This same look can be accomplished with black “work” pants as well if you’re more comfortable that way. Just wear a flowy tank and some business casual pants (mine are under $30!) and you’re good to go.


back to school night teacher outfit pants

Shop This Look:

back to school teacher outfit with pants


Loft Teacher Discount

First Day With Students

On the first day with your kiddos, you want an outfit that communicates professionalism, confidence, and also is fun and welcoming. When I was a brand new teacher I used to wear a business-type suit on the first day to make myself look older. I was so uncomfortable and stiff that I’m sure it showed. Now I opt for something much more comfortable and “friendly” looking, but still professional, and this works better for me. This same floral kimono is perfect for Day 1 with the addition of some white slacks, a rust colored tee, and some pretty wedges. I teach high school students, so I almost always wear heels the first few days to make me as tall as or taller than many of my students. Well, except for the basketball players. I love a more colorful, cheerful look for Day 1 because it communicates warmth and welcome. And that’s good because then my clothes are welcoming the students, not just my awkward wave like in the photo below. :-/

teacher first day outfit

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first day with students teacher outfit


Casual Friday

Once you’ve kicked off the first week or two of school in style, if your school is like mine, casual Fridays roll in. At my school we can wear jeans any day, as long as we dress them up and still look professional. The look below is something I would wear on a regular day, but if your school only allows jeans on Fridays, you could pull it out then. At any rate, the point is that a kimono like this can help you keep your more casual look stylish and slightly dressier than just plain jeans and a tee. Make it a graphic tee and some comfy Birkenstocks and you’ve got a comfy, stylish vibe that’s perfect for those less formal days.

teacher outfit casual

Shop This Look:

teacher outfit casual friday

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More Back-to-School Outfit Ideas from Teacher-Bloggers

These ladies are always inspirational and fun, so be sure to subscribe to their blogs and follow their other social accounts as well!

Do you have go-to teacher outfit formulas that work for you for those important days? I’d love to see them and I know others would too, so feel free to tell us about them or share photos in the comments.

And for those who have already headed back to school or will be soon, have a great year!


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Vionic Shoes_Kirra Backstrap Sandal

Stitch Fix 45 Review: It’s All Good!

You requested it, you’ve got it: another Stitch Fix review! Spoiler alert: this time I kept all five items.


Note: This post contains affiliate links. Clicking on these links may result in my earning a commission or referral fee at no cost to you.  As always, all opinions expressed here are 100% my own.


Market & Spruce “Lorraine” Printed Short – $54

In my previous Stitch Fix, I had requested and received some printed shorts. They were cute, but the colors really weren’t ones I wore a lot and they didn’t have pockets (a deal-breaker for me!). So my stylist sent another pair for me to try in this Fix. They were perfect! The material isn’t too tight and has some stretch. The shorts are shorter than I’m used to, but not so short that I was uncomfortable in them. At $54 they were a bit out of my price range, but since I ended up buying all 5 items in this Fix, I received a 25% discount, making them much more affordable.

Verdict: Kept them

Stitch Fix Market and Spruce Lorraine Printed Short

Also pictured here:


2. Liverpool “Betty” Chambray Shirt – $64

I have a darker blue chambray shirt, but I’ve been looking for one in this lighter color for spring and summer. The material is lightweight and has some stretch, and the length is perfect for either tucking or knotting. Also, this chambray shirt has sleeves with buttons to hold rolled-up cuffs. As a teacher who moves her arms around a lot when teaching, this is much-appreciated. Again, $64 was a little higher than I am used to paying for a shirt, but Liverpool is a great brand and I did get the 25% off.

Verdict: Kept it

Stitch Fix Liverpool Betty Chambray Shirt

Also Pictured Here:


3. Just Black “Rogers” Boyfriend Jean – $78

These jeans are SO comfortable! They feel like a cross between comfy leggings and jeans. I like that they are on the loose side. One thing I didn’t like is that they are just too long on me. In this photo I cuffed them, but I have since cut them off to be raw hem crops of about the length you see here. I like them so much better that way! These jeans have just the right amount of distressing — I’ll definitely be able to wear them to school or church.

Verdict: Kept them

Stitch Fix Just Black Rogers Boyfriend Jean

Also Pictured Here:


4. Sanctuary “Vechi” Twist Knit Top – $48

At first I wasn’t even going to try this tee on. I already have a plain gray t-shirt, so why would I need another? Then I lifted the shirt up to look at it and saw…..those….sleeves. They have little slits with a twist on the sides, and I love that it’s not open like a cold shoulder top. Instead, it’s more subtle and classy. Then it’s also got the twist so you don’t need to worry about tucking it in or letting it hang. This top is a keeper!

Verdict: Kept it

Stitch Fix Sanctuary Vechi Twist Knit Top

Also Pictured Here:


5. Kaileigh “Cara” Mixed Material Tank Top – $48

This is my favorite piece in the whole set. The front side features gauzy, breezy blouse material with a fun elephant print pattern. The back is a jersey-type material with stripes. Looking at this photo I don’t think I’ll be wearing this top with white jeans, but it looks fabulous with pretty much any shade of blue denim. Even better, this tank isn’t cut too low in the front, and the straps are more generous. It’s a tank you can move around in without worrying about coverage. I plan to transition this right into fall with cardigans and jackets.

Verdict: Kept it

Stitch Fix Kaileigh Carah Mixed Material Tank Top

Also Pictured Here:


All in all, this was a great Fix. It’s been a while since I’ve purchased all 5 items in a Fix. In all 45 of my Fixes I think it’s only happened 1 or 2 times before. The total would have been $292, but with the “Buy All 5” discount of 25% off, the total came to $219. That’s still a lot of money, but it didn’t hurt so much in this particular Fix because I also happened to have a $150 Stitch Fix gift card to blow, so it felt like I was only spending $69. High five!


Speaking of gift cards, Stitch Fix gift cards are the perfect gift idea for those hard-to-buy-for people. They have Stitch Fix styling for all sizes of women, including maternity, they do men’s styling (REALLY wish I could talk my hubs into trying this….still working on it), and now they even have kids’ styling! My 9-year-old son reluctantly agreed to give it a try after I asked him for the millionth time. He hates trying on clothes, but it was the idea that he could do it at home instead of going….gasp….clothes shopping that tipped the scales in my favor. Watch for an upcoming post with his Stitch Fix Kids review sometime soon!

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Teacher-Budget Friendly Back to School Style Guide!

Back to School in Style Supply List for Teachers

They’re out in full force now. You know what I’m talking about: aisles and aisles of back-to-school supplies. Seeing back-to-school displays in early July makes me cringe, but now that we’re nearing August,  I have to admit it’s kind of exciting. This is the time of year when teachers are hitting Pinterest for new lessons, classroom decorating ideas, and cute storage and organization solutions. In the midst of all of this, take some time to make sure you’ve got your teacher wardrobe ready to go, too. One of my favorite online destinations for cute and affordable teacher (and mom!) clothes and accessories is Jane. Today I’m super-excited to be partnering with Jane to bring you a budget friendly (yes, even TEACHER budget friendly!) style guide with picks to help you ease the transition from summer to school year. And bonus, they have tons of great back-to-school deals coming in every day.

Daily Boutique Deals

Note: This post contains affiliate links. Clicking on these links may result in my earning a commission or referral fee. I appreciate your support of my blog. As always, all opinions expressed here are 100% my own. If you’re seeing it here, it’s a product or brand I use, like, or believe is something you would like, too.


Your TEACHER STYLE Supply List

Heading back to school involves some key occasion-based outfit needs. This style guide is broken down into outfits or pieces you can use on these universal teacher situations.


All of these pieces come straight from, but some may no longer be available because these are flash sales, y’all. Flash sales means they’re only for sale for a few days, and every day you can check back for new goodies! Sometimes they bring back popular items, so keep checking back if there’s something specific you’re looking for.


Faculty Inservice Training / Meeting Day

Most of us will have a day of meetings, training sessions, and if you’re very, very lucky, some time to work in your room the day before students arrive. On that day you need something comfortable and casual, but also put-together. That’s the day new staff are introduced and you’ll probably be interacting with them, along with the rest of the staff and administration. You can make a good first impression while still being comfortable.

Cute Tee

You can always find cute teacher tees like these at Jane. I love the green one!

Jane cute teacher tees

Shorts or Jeans

Casual bottoms are fine for most beginning-of-the-year workdays. I like to go with cute distressed jeans or a pair of comfy joggers, or if it’s a really hot day shorts are a great choice.

  jane comfy jeans 


jane comfy cutoff shorts


Comfy Shoes

Informal inservice and work days are perfect for a cute pair of sneakers.

cute sneakers


Day 1: The Marathon

I love the first day of school! You anticipate it (and okay, maybe dread it a little, too) and then before you know it, it’s here. All of your shiny, new students are there and you’ve got to make a good first impression that says, “I’m competent, confident, capable, and caring, and I’m glad you’re here!” Again, comfort is key: it’s August and the temps might be up there; on the other hand, dressing up shows your students you’re a professional with high standards (or at least makes them THINK this on the first day – LOL).


Fun, Classy Blouse

A top like this one is perfect for the first day of school because it’s easy (no tucking in necessary, and you don’t need to roll up sleeves or fuss with a blazer), it’s comfortable (slightly flowy and the shorts sleeves are perfect for August), and it looks professional.

jane white blouse

Professional (but Comfortable!) Pants or Skirt

I most often go with a pair of comfy, yet professional pants on Day 1. I love that the striped ones below are linen, a bonus if it’s hot. Some years I wear a skirt – usually a knee length midi or a maxi that’s not too billowy. The chambray maxi below would be perfect. These two bottoms both happen to be striped. Obviously, you don’t have to go with stripes, but I like how a patterned bottom is a little more fun. It’s a little more exciting and cheerful than solids, which is just the mood you want to set on your first day with kiddos.


jane tie waist striped linen pants  


jane chambray striped maxi skirt



Flat sandals are a go-to for me on Day 1, but I’ve had teachers tell me before that they are not allowed to wear open-toed shoes to school, so a cute pair of flats would also fit the bill. These footbed sandals are perfect because they provide more support than super-flat sandals would, and you’ll be on your feet all day.

jane comfy sandals


jane flat mules


Back-to-School Night or Parent-Teacher Conferences

The parents are coming! The parents are coming! Quick, spit-shine that room and organize some student work and activities for parents when they come. Also, choose an outfit that radiates professionalism and also warmth. You also want an outfit that’s comfortable for walking around, talking, and shaking hands.


A comfy (are you seeing a theme here? LOL) dress is my default outfit for Back-to-School Night. When the dress has pockets, it’s even better! It gives you something to do with your hands when you’re not shaking hands with parents or pointing out their child’s learning areas. A dress is also a great option for Day 1 with the kiddos, again, especially if it has pockets.

jane jersey midi dress


jane summer dresses

Nicer Shoes

Lots of teachers I know pack a pair of dressier shoes in their tote to swap out before Back to School Night or Parent-Teacher Conferences. Cute, comfy shoes are great for the day-long teaching, but I always get a little boost of confidence from stepping into a pair of heels, albeit, low heels or maybe wedges. Let’s not get crazy here.

jane low heel sandals


jane sapadrille sandals


Everyday Essentials

On those “normal” days (do teachers even have normal days? topic for another time…) it’s great to have closet staples you can throw together effortlessly. Let’s face it, when you’ve been up late grading or planning for the next day, choosing an outfit is not on your priority list. With a good stock of everyday essentials, you can focus on your classroom, not your closet.

Layering Blouses and Tees

Every teacher wardrobe needs some simple pieces that can be worn alone or with layers. It’s good to have some solids and some fun prints to mix things up.

solid blouses jane

jane print tees

Cardi or Kimono

For those days when the air conditioner is cranking, or when the winter wind is howling through the cracks around your window, a cardis and kimonos are great layering pieces. Not all schools allow teachers to wear jeans on weekdays, but ours does as long as we dress them up, and cardigans and kimonos are the perfect way to do that.

jane long cardigan


jane floral kimono


Fun Statement Jewelry

A great way to jazz up an otherwise ordinary outfit is to add a pair of trendy earrings or a great necklace. And no, I’m not talking about wearing plastic apples (not that there’s anything wrong with that). I love to find colorful, lightweight pieces like these that won’t get in the way of my teaching.

jane tassel earrings


jane necklaces


A Hold-It-All Bag

Every teacher needs a great tote bag to haul papers, supplies, lunches, and everything else to and from school each day. Jane always has a good selection of teach-worthy bags, in everything from fun prints to chic designer-inspired (and personalizable) faux leather.

jane tote bag


jane faux leather tote


Daily Boutique Deals


Treat Yo’ Self, Teech

You know how when you have cute workout clothes, you’re more excited to get your sweat on? Well it works the same way in the classroom. If I have a cute and comfortable “teaching” outfit lined up, I feel more confident, together, and ready to tackle the day with my kiddos. Consider it an investment in your motivation bank. Well, that’s how it works for me anyway.


It’s still July so you probably have a few weeks left to plan and prep for the year. Be sure to hop on over to Jane for some great finds. It’s a goldmine for teachers, not just for budget clothes and accessories, but also for inexpensive fun classroom items, kids’ and men’s clothes and accessories, and even home decor items. If you follow me on Facebook, you’ve seen the super-fantastic Jane items for teachers and moms that I occasionally share there. Oh, and be sure to check out their selection of graphic tees. There are always funny, inspirational, and even teacher-specific ones. They are my go-to for casual Fridays when I’m not wearing school spiritwear. You’ll want to check back often because they add new deals every day! Happy back-to-school shopping, teacher-friends!

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