7 Dresses for Teachers That are Classy, Comfortable + Completely Affordable

This post: Professional outfits for teachers that won’t break the bank.

This school year just might feel normal, am I right?

Fingers crossed, of course!

If you’re a teacher, then you’re probably heading back to class in a few weeks (goodbye, Zoom!). And of course that means you’ll need an amazing wardrobe to carry you through the new school year.

I’ve got some stylish teacher outfit ideas for you today.

Full disclosure: I’m a home educator, which means I can “teach” in my pjs.

But I don’t!

I love dressing well, even if I’m at home with my kids all day. For the past three years, I tutored + directed at our Classical Conversations homeschool community, so I do know that teacher outfits need to be three things:

  • comfortable
  • easy to wear + wash
  • stylish (because who wants to look boring?)

So this post is a nod to you amazing teachers… + your wardrobes. xoxo

Some of the links in this post are affiliate links.  As a ShopStyle Collective member, I earn a small commission when you click on these links. Thanks for supporting this site! xoxo

Dresses for Teachers

The pieces I’ve curated for this post are washable, easy to move around in, + all of them cost less than $70 (most are in the $40 to $50 price range).

I’ve also included a few accessory or beauty products to polish off your outfit.

>> If you enjoy my teacher outfit ideas, please hit a share button to spread the love.

>> Ready to shop? Simply click the photos + links in this post.

Teacher style #1. Blouson Midi Dress, by Wayf at Nordstrom.

This gauzy dress is perfectly feminine +soft! The sleeves + hem length provide great coverage without being too hot (if you want something to bring up the neckline consider wearing a Halftee under the dress).

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The grey midi (pictured above) is sold out, but the style is available in a lovely cream. Polish off your look with a touch of Mac lipstick in “chili” + these nuse block sandals.

#2. V-Neck tiered midi dress, by JCrew Factory

Tiered midis are trending this season! I recently ordered this lovely midi+ can’t wait to wear it.

I ordered it in “antique navy anchor,” pictured above, but it’s also available in a “bold hibiscus” pink.

Pair it with this straw handbag + pair of espadrille wedges, and people will think you’re not quite ready for summer to end. xoxo

#3. Smocked maxi dress, by Old Navy

Priced at just $49.99, this maxi is a weekday must-have! Dress it up with a pretty cardigan or denim jacket + strappy sandals.

#4. Sheath dress, by JCrew Factory

This pretty sheath dress is just the right amount of classy + comfy! Suprisingly, it’s machine washable + can easily be dressed up or down. (It’s also available in black.)

This dress is one of my personal favorite teacher outfit ideas. For a sophisticated look, pair it with a coin necklace+ D’orsay flats.

#5. Cotton/Poplin Tiered Dress, by JCrew Factory

This lovely dress is pretty-in-pink; isn’t the “tea rose” color delicious?

Take it to the next level with this preppy pink lipstick + strappy sandals.

Teacher style #6. Retro Blue Midi, by JCrew Factory

Here’s a vintage-inspired midi that makes a fashion statement all by itself.

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Dress it up a bit with an initial necklace + white slides by New Day.

#7. Striped V-Neck Midi, by JCrew Factory

This comfy dress will take you from weekday to weekend… + probably leave you dreaming of the coast! I own this dress + style it with these leather slides + a hat.

For a relaxed work look, pair it with a beach tote + navy espadrilles.

More preppy teacher style:

Before you go!

If you like preppy + pretty, check out the Simplified Planner, by Emily Ley.

The teacher planner is perfect for starting off the school year strong.

For a limited time, receive a FREE classroom bundle when you buy the teacher planner. Details are right here.

Your turn.

Any favorite dresses for teachers? Drop your recommendations below.

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