11 Comfy Teacher Outfits: Top Picks for Style and Comfort

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11 Comfy Teacher Outfits: Top Picks for Style and Comfort

Are you looking for some ideas for comfy teacher outfits that are stylish too? If so you’ve come to the right place. In this post we’re going to get some outfit inspiration from my favorite stylish teachers on Instagram. Plus, I’ll show you how you can copy their style with pieces from Amazon.

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What are the top trends for comfy teacher outfits this year?

Here is what I’m seeing and loving for teacher outfits this year:

  • Jumpsuits-Yes, you have to add some of these to your teacher wardrobe this year.
  • Wide Leg Pants- From linen palazzo pants to wide leg jeans it all works and I want it all!
  • Flowy material, Add some loose dresses and flowy tops to your closet this year.
  • Teacher T-shirts. For a look that won’t go out of style pair cute teacher tees with pants and skirts.

Let’s check out all of these trends and more in this post.

1 | Wide Leg Jumpsuit Teacher Outfit Idea

Jumpsuit Teacher Outfit Idea
Image Source | hannabethh

Hanna Beth is a first-grade teacher from Oklahoma, and she knows how important it is to stay comfortable in the classroom. You need those teacher outfits that you can move around and bend down to your students’ level and still look great.

Wide leg jumpsuits are a great outfit for the comfort and style you’re looking for. Pair them with sneakers and a cute headband and you’re ready for your day. If you want to give this look a try check out how you can pull it off below.

Top Picks for Wide Leg Jumpsuit Outfit

Jumpsuit outfit on Amazon
Where to Find | Jumpsuit | Headband | Sneakers | Shirt

About this Jumpsuit Teacher outfit

  • Jumpsuit The wide leg style is really in right now and I feel like it just adds to the comfort too.
  • Shirt For the shirt oversized works well with this outfit so be sure to size up.
  • Sneakers You can never go wrong with a versatile pair of white sneakers, I love Pumas.
  • Headband You can elevate a simple pony tail with a pretty headband like this pink one with faux pearls.

2 | Maxi Dress and Teacher Tee Outfit Inspiration

Maxi Dress and Teacher Tee Outfit
Image Source | lifewithmrsjamaica

Pre-K teacher, Jamaica, shows us another way to style your favorite teacher t-shirt. You can wear a skirt or layer your shirt over a maxi dress. It looks great with a neutral pair of sandals and a cute pencil lanyard. If you want to copy Jamaica’s style check out my top picks below to pull it off.

Where to Find Maxi Dress and Teacher Tee Outfit

Teacher Shirt with Maxi Dress
Where to Find | Dress | Shirt | Sandals | Lanyard

About this Teacher Shirt and Dress Outfit

  • Dress You could copy this outfit with a skirt, but I think the maxi dress would be the comfiest option. Simply layer the t-shirt over the top of the dress.
  • Shirt To copy this style you will want to tie a knot in your t-shirt. For the most flattering look tie it about where an empire waist dress would hit. Find a shirt like this with the wording at the top so you don’t cut it off when you tie it.
  • Sandals Braided sandals add texture to the outfit.
  • Lanyard For a fun accessory try a cute teacher lanyard like this.

3 | Chunky Sweater with Jeans Teacher Outfit

Teacher Outfit with Jeans and Sweater
Image Source | kathyvkellogg

5th grade teacher, Kathy shows us how you can elevate your favorite blue jeans with a colorful chunky cardigan for a cute look in the classroom. Pair with your favorite sandals and accessorize with a cute lanyard and you’re ready for a day with students. If you want to copy this style, check out my top picks below.

Top Picks for Sweater & Jeans Teacher Outfit

Jeans and Sweater Outfit Idea
Where to Find | Sweater | Jeans| Sandals | Lanyard

About This Sweater & Jeans Teacher Outfit

  • Sweater Chunky sweaters are so cozy, and a V-neck is flattering for all body types.
  • Jeans If you want to be on trend with your denim this year add some light colored high waisted wide leg jeans to your wardrobe.
  • Lanyard If you’re going to wear it every day it might as well be cute.
  • Sandals Leather braided sandals in a neutral will go with everything and add a little texture to your outfit too.

4 | Leggings and Oversized Sweatshirt

Teacher Outfit with leggings and sweatshirt
Image Source | fashionablylindsey

Kindergarten teacher Lindsey is wearing a cute pair of faux leather leggings with a cozy oversized sweatshirt. This outfit would look great with any pair of black leggings. To complete the look, her black and white lanyard coordinates with her outfit perfectly. If you want to copy this outfit idea, check out how to do it below.

Leggings and Sweatshirt Teacher Outfit Top Picks

Legging and crewneck outfit idea
Where to Find | Sweatshirt | Leggings | Shoes | Lanyard

About this Leggings & Crewneck Teacher Outfit

  • Leggings Black leggings will never go out of style. The faux leather ones are hot right now.
  • Sweatshirt An oversized V neck looks great paired with leggings and will keep you cozy all day. I’m also loving this one.
  • Shoes These sneakers are cute and practical and the touch of black goes perfectly with this outfit.
  • Lanyard To complete the look why not add a cute black and white lanyard?

5 | Black Jumpsuit Teacher Outfit

Black Jumsuit teacher outfit
Image Source | livingalatte

Melissa, from Orange County, California has mastered the art of looking great while staying comfortable in the classroom. It starts with a versatile piece like this black jumper. If you’re loving it too check out below how you can copy her style.

Where to Find Black Jumpsuit Teacher Outfit Idea

black jumpsuit on Amazon
Where to Find | Jumpsuit | Jean Jacket | Sandals

About This Black Jumpsuit Teacher Outfit

  • Jean Jacket This is an outfit staple that helps you take your summer outfits into fall and winter.
  • Sandals Black two strap sandals are a versatile shoe that you can wear with a lot of outfits.
  • Jumpsuit It’s soft and it has pockets, what more do you need?

6 | Teacher Outfits with Joggers

Teacher outfit with Joggers
Image Source | hannabethh

What is comfier than a pair of joggers? Hanna Beth has tucked in a long black t-shirt and paired her joggers with comfortable running shoes. Pick a fun color instead of grey to elevate the look a little. Check out my top finds to steal this style below.

How to Copy the Jogger Teacher Outfit

women's outfit idea with sweatpants and sneakers
Where to Find | Joggers | Shirt | Sneakers

Jogger Teacher Outfit Details

  • Joggers These pants come in tons of fun colors so you can choose your favorite.
  • Sneakers I’m loving the little touch of gold on these Adidas.
  • Shirt This long sleeve black tee is super comfy and is a top pick for nurses.

7 | Jeans and Teacher Sweatshirt Outfit

Jeans and Sweatshirt Teacher Outfit
Image Source | ashionablylindsey

You should follow Lindsey on Instagram if you like to get daily ideas for teacher outfits. Right now she’s rocking a cute teacher crewneck with jeans and sneakers for a look that’s casual and cute at the same time. Check out some ideas to create a similar look below.

Top Picks for Teacher Crewneck & Jeans Outfit

teacher sweatshirt and jeans
Where to Find | Sweatshirt | Stanley Cup | Sneakers | Jeans

Sweatshirt & Jeans Teacher Outfit Details

  • Sweatshirt A cute teacher crewneck is wardrobe staple.
  • Stanley Cup You have to take care of yourself and stay hydrated throughout your day and I feel like it helps when you have a cute cup!
  • Sneakers Another win for white sneakers that go with every outfit. You can’t go wrong with Adidas.
  • Jeans Levis straight leg jeans look great on all body types and are available in plus size too.

8 | Green Overalls Teacher Outfit Idea

Overalls Teacher Outlift Idea
Image Source | livingalatte

Here Mellissa has paired a soft pair of cotton overalls with two strap tan sandals. A plain white shirt is the perfect option to layer under your overalls. Check out my picks to steal her style below.

Top Picks for Overall Teacher Outfit

overalls with sandals outfit
Where to Find | Overalls | Sandals | T-Shirt

About this Overall Outfit

  • Overalls These come in a ton of colors, this is my absolute favorite.
  • Sandals The natural color of these shoes work nice with the overalls and would go with a ton of different outfits.
  • T-Shirt Add a plain white tee under your overalls for a cute, casual look.

9 | Teacher Outfit with Palazzo Pants

Palazzo pants teacher outfit
Image Source | lifewithmrsjamaica

Teacher of the year, Jamaica shows us how to elevate your bright palazzo pants with a ruffle top. She always adds cute accessories to help take her style up a notch like these fun earrings. If you’re loving her style, too check out an idea below to pull off this look.

Top Picks for Palazzo Pants Teacher Outfit

palazzo pants outfit inspiration
Where to Find | Pants | Shirt | Earrings

Palazzo Pants Outfit Details

  • Pants The wide waist band in these palazzo pants makes them super comfy and forgiving. They come in tons of different colors too.
  • Shirt The ruffle and the chiffon material elevates the outfit just enough.
  • Earrings These wooden pencil earrings would add a playful touch to your outfit.

10 | Wide Leg Overalls Outfit for Teachers

comfy teacher outfit idea with wide leg overalls
Image Source | kathyvkellogg

Kathy shows us an easy style choice pairing your cozy overalls with your Birkenstocks. Do you love this look too? If so check out my top picks to copy this style below.

Where to Find Cozy Overalls Outfit

cute overalls on Amazon
Where to Find | Overalls | Birkenstocks | Lanyard | Shirt

Cozy Overalls Teacher Outfit Details

  • Overalls There are loose and baggy which would add to the coziness. They are available in several colors.
  • Lanyard Look closely at this lanyard, it has retro flowers and smiley faces which would add a fun touch to your daily style.
  • Birkenstocks A teacher must have, they’re super supportive and go with everything.
  • Shirt Keep it simple and layer a white t-shirt under your overalls to complete the look.

11 | Midi-Skirt and Teacher Tee

Teacher Shirt and Skirt Outfit Idea
Image Source | hannabethh

Hanna Beth shows us another comfy and stylish teacher outfit idea with a stretchy high waisted midi-skirt in a fun color. Grab a pair of neutral sandals and accessorize with a matching watch band. Pair it with a colorful teacher tee and you’re ready for an active day in the classroom.

Check my top picks for this outfit idea below.

Where to Find Teacher Tee and Midi-Skirt Outfit

Teacher Shirt and Skirt Outfit on Amazon
Where to Find | Shirt | Skirt | Watch Band | Sandals

About This Skirt and Teacher Shirt Outfit

  • Shirt Would your students appreciate if you rocked a Taylor Swift Inspired Teacher Tee? This shirt runs small so size up for the perfect fit. This one is also available in plus sizes.
  • Skirt Look for a skirt with stretch or an elastic waist for added comfort. This one is also available in plus sizes and different colors and patterns.
  • Watch Band Ditch the boring watch bands and elevate your outfit with this colorful one.
  • Sandals Stylish and practical leather slip on sandals go great with skirts and dresses.

Now that we’ve got a ton of outfit inspiration from my favorite Instagram teachers let’s check out some comfy and stylish essentials to keep your wardrobe stocked up.

Comfy Teacher Outfits Essentials

Shirts for Teachers

When it comes to teacher wardrobe essentials, a variety of shirts is a must-have. Start by stocking up on some comfortable t-shirts, blouses, button-up shirts and of course teacher tees. They can be mixed and matched with skirts or pants for a versatile look. Choose fabrics that are breathable and easy to care for, to ensure comfort throughout the day.

  • T-shirts: Solid colors or simple patterns work great because they can be layered with cardigans or blazers.
  • Blouses: Look for loose-fitting and breathable materials, such as cotton or linen.
  • Button-up shirts: These can be worn with dress pants or tucked into skirts for a professional look.
  • Teacher Shirts: You can always find some cute teacher tees. Try something new and on trend by pairing them with a leopard, floral print or bright colored skirt.

Top Picks for Teacher Shirts

Cute teacher tees are a must have to every teacher wardrobe. Check out some of my favorites below.

cute teacher shirts

Add a little color to your wardrobe with a cute teacher tee. Check out below where to get each of these.

Where to Find Teacher Shirts

Looking for more cute teacher tees? Check out my latest designs here.

Best Pants for Teachers

Having a selection of comfortable pants in your wardrobe is essential for those long days in the classroom. Jeans and dress pants provide you with options to dress up or down depending on the day. Be sure to choose materials that are stretchy and breathable:

  • Jeans: If your school lets you wear jeans then find some with stretch for ultimate comfort. If you want to try to look more professional you can pair them with a nice blouse, button-up shirt or a blazer.
  • Dress pants: Find pants with an elastic waistband for added comfort during long school days. Wide leg pants are in style right now and bonus they are extra cozy.

My Top Picks for Teacher Pants This Year

Like I said the wide leg pants are in style this year and super cozy. Check out my favorites that you can get on Amazon below.

Best wide legs pants on Amazon

Where to Find Wide Leg Pants

Teacher Dresses

Dresses are another great option for creating a comfortable yet stylish teacher outfit. Pair them with your favorite sneakers or sandals for a cute look. Here are a the most popular styles for teachers.

  • Midi dresses: These hit around mid-calf and usually come in a variety of comfortable materials such as jersey or cotton.
  • Shirt dresses: These mimic the look of a button-up shirt or a t-shirt but are longer, making for a simple and chic dress option.

Speaking of teacher dresses, I wrote a whole post about it, you can check it out here…

20 Teacher Dresses for All Day Comfort & Style

Best Shoes for Teachers

Comfortable footwear is critical for teachers given the amount of time you spend on your feet. There are tons of options for flats, sneakers, and sandals that provide support for long days in the classroom and will add a little style to your teacher outfits too.

  • Flats: Flat shoes with cushioning and support are essential. Look for options with a rubber sole.
  • Sneakers: Stylish sneakers can be a great option, especially if you're on your feet all day. They look cute with dresses or pants. I love white ones because they go with everything.
  • Sandals: Comfortable sandals with good arch support can be a lifesaver and they look great with dresses and pants.

Must-Have Teacher Accessories

To complete your teacher outfits here are the top accessories that I’m loving this year.

  • Big Earrings: Go bold with your earrings and try something chunky and eye-catching. If you want a playful look add teacher themed ones like pencils or apples.
  • Stylish Lanyard-Who says your lanyard needs to be boring? There are tons of cute ones now, you can check them out here, that will elevate your style every day.

My Top Picks for Teacher Earrings

I think it’s fun to add a little color and playfulness to your teacher wardrobe with big earrings. Check out my favorites below that you’re sure to get tons of compliments for.

teacher earrings

Where to Find Teacher Earrings

Frequently Asked Questions

What are some comfortable clothing options for teachers?

The good thing is right now loose-fitting clothing is in style. Incorporate loose dresses, skirts, flowy shirts and wide legged pants into your wardrobe this year. Also, look for breathable fabrics like cotton and linen because they will let you move easy, will keep you cool and are easy to wash.

How can teachers look both professional and casual?

So, you want to be comfy and casual but still professional right? The best way to do this is to mix casual pieces with professional ones. For instance, pairing a simple blouse or shirt with a tailored blazer or a loose dress with a cardigan and statement necklace allows you to stay comfortable while still looking polished.

What are some wardrobe essentials for teachers of different body types?

There are several wardrobe essentials that look great on all body types and will help you make the most out of the pieces that you have. These include a classic white blouse, black pants, pencil skirts, blazers and empire waist and wrap style dresses. Mix neutral tones and bright colors to add variety to your wardrobe and create outfits that complement your individual style.

I hope you got some inspiration for stylish and comfy teacher outfits that you can add to your wardrobe this year. For daily style inspiration follow the teachers featured in this post on Instagram. Feel free to save your favorite outfit ideas to your Pinterest boards. To do that just click on the picture, then the P and choose your board.

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