20+ Teacher Workwear Looks

I’m excited to bring you 20+ teacher workwear looks to inspire your wardrobe. I’ve heard from my teacher friends that looking professional, put together, and feeling comfortable are top priorities when it comes to your work wardrobe. From classic blazers to cozy sweater dresses, these outfits will have you feeling confident and looking stylish as you lead your students through another successful school year!

SHOP TEACHER WORKWEAR STAPLES

PAPER BAG POCKET SKIRT

SKIRT | TOP (left) | BAG (left) | BELT | FLATS | TOP (right) | BAG (right)

This paper bag pocket skirt is a versatile piece that can easily elevate any teacher’s outfit. Pair it with a chambray button-up shirt and a black bag for a classic look. You can also style it with a ruffle tie-neck blouse for a feminine touch. Opt for flats for a practical footwear option that can take you from classroom to recess with ease.

TOP | SKIRT | BAG | FLATS

Another way to style this khaki skirt is to pair it with this olive green flutter sleeve top and my go-to leopard print flats. This color combination makes this look the perfect summer-to-fall transitional outfit.

TIERED MIDI SKIRT

SKIRT | TOP (left) | BOOTIES (left) | BAG (left) | TOP (right) | HEELS (right) | BAG (right)

This tiered midi skirt is the perfect addition to your fall wardrobe. It can be dressed up or down with the switch of a few accessories. For the perfect classroom look, pair it with a puff-sleeve sweater and pointed-toe heels. Opt for a casual look by pairing the skirt with a comfortable v-neck sweater and western-inspired booties.

SKIRT | SWEATER (left) | BAG (left) | HEELS (left) | TOP (right) | FLATS (right) | BAG (right) | BELT

The puff sleeve henley paired with embellished flats offers a comfortable and put together outfit that can easily transition from the classroom to parent-teacher conferences. For a look that can carry you into fall with ease, pair this skirt with a v-neck cardigan and slip on a pair of heels.

CHAMBRAY SWING DRESS

DRESS | BAG | BOOTIES

This chambray swing dress is a must-have addition to your work wardrobe. It pairs perfectly with booties and your favorite work tote!

DRESS | BLAZER (left) | HEELS | BAG (left) | BLAZER (right) | BAG (right)

Layer your favorite blazer over the top of this chambray dress to transition this dress into fall. Two of my favorite blazer options are this linen blazer on the left and the khaki blazer on the right.

DRESS | CARDIGAN | BAG | FLATS

Another way to style this chambray dress is to pair it with a cozy cardigan. The rich camel color adds warmth to your look, and the length of the cardigan draws your eyes up. To add a touch of personality, opt for leopard flats and a stylish black leather bag to hold all of your teacher essentials.

BLACK CROPPED FLARE PANTS

PANTS | TOP (left) | BAG (left) | FLATS | TOP (right) | BAG (right) | HEELS

Black cropped flare pants are a closet staple that every teacher should own! When paired with an oversized poplin shirt and mules, the outfit transforms into an effortlessly put together look that exudes professionalism. For a feminine touch, pair these pants with a flutter-sleeve top and heels.

PANTS | CAMI | CARDIGAN | FLATS (left) | BAG (left) | FLATS (right) | BLAZER

The versatility of these pants allow you to dress them up or down, making them suitable for any occasion at work. Layer a blazer or longline cardigan over a silk camisole for a classic fall look. Complete the look with statement flats and a vegan leather tote bag.

SHIRT DRESS

DRESS | BAG | FLATS

This shirt dress is a chic and modern option that is perfect for the classroom. Pair it with neutral mules and your favorite work tote, and you’re ready to take on the day!

DRESS | SWEATER (left) | BOOTIES | BAG (left) | CARDIGAN | HEELS | BAG (right)

There are countless ways to style a shirt dress! Two easy options to style this dress for fall are to pair it with booties or layer it with a cardigan and heels for a polished look.

DRESS | SWEATER | BELT | BAG | SHOES

With the addition of a cozy sweater and a belt, you can completely transform the entire look. This might be one of my favorite ways to style this outfit. This look can easily go from the classroom to dinner with friends.

FITTED MIDI DRESS

DRESS | FLATS (left) | BAG (left) | SWEATER (right) | BAG (right) | FLATS (right)

A fitted midi dress is a perfect option for any teacher who wants to look great and feel comfortable throughout the day. I styled it here with leopard flats and a camel work tote for an easy and professional look. Pair it with embellished flats and a striped sweater, and you’re ready for fall!

DRESS | JACKET | BAG (left) | SNEAKERS (left) | BAG (right) | BLAZER | HEELS

I love that this dress can easily be dressed up or down depending on the occasion. For casual Friday, opt for a denim jacket and white sneakers. To elevate the look, layer a black blazer over the top and opt for pointed-toe heels.

Looking for more inspiration for your back-to-school wardrobe? Check out these 25 teacher workwear outfits!