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 Jane.com, 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!

everyday teacher style signature

Daily Boutique Deals


  1. Some very cute options in clothes and shoes. Guess it’s time to take inventory of my closet!

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