Chalkboards & Chic: A Teacher’s Guide to Stylish, Modest Fashion from

There’s something truly special about the start of a new school year. The fresh notebooks, clean whiteboards, sharpened pencils — and of course, the excitement of meeting a new group of students. But let’s be honest — one of the best parts? Back-to-school fashion for teachers!

At Lena Layne, we know that teachers do everything. From managing classrooms to planning lessons and staying late for parent-teacher conferences, educators are real-life superheroes. That’s why we believe you deserve a wardrobe that works just as hard as you do — while keeping you comfortable, confident, and completely you.

Whether you’re a kindergarten teacher with a love for fun prints, a high school educator keeping it polished and practical, or anywhere in between, this guide is full of cheerful fashion inspiration to help you feel your best in the classroom — all year long.

1. Start with a Solid Foundation: Modest Basics That Go the Distance

Think of your wardrobe like your lesson plans — it all starts with a great foundation. At Lena Layne, we recommend stocking up on comfortable, modest basics that you can mix and match all week long.

Here are a few teacher must-haves:

Layering tees and camis in neutral tones
Modest crewneck or V-neck tops in soft, breathable fabrics
Stretchy pencil skirts that don’t ride up
Knit midi dresses that move with you
Comfy cardigans for chilly classrooms

These staples are easy to dress up or down and help you build countless outfits with just a few key pieces.

2. Add Personality with Prints and Pops of Color

Your students love seeing your personality shine — so don’t be afraid to let your wardrobe do the talking! Add fun prints like florals, polka dots, or stripes to your weekly rotation. Try a patterned midi skirt with a solid top, or rock a printed button-up dress with your favorite flats.

Need ideas?

A playful graphic tee paired with a flowy maxi skirt
A colorful cardigan layered over a neutral outfit
A bold printed midi dress with a cute belt to cinch the waist

At Lena Layne, we carry prints in sizes S–3X, because fashion should be fun, flattering, and for everyone.

3. Comfort Is Key (Especially on Your Feet!)

Let’s face it — teachers are on their feet a lot. So while we all love a cute shoe moment, comfort always comes first. Look for:

Cushioned flats or loafers
Stylish sneakers that match your outfits
Low-heeled ankle boots for fall and winter
Slip-on mules for quick outfit elevation

Don’t forget to treat yourself to some fun socks too — they’re a cheerful little detail your students might just notice and love.

4. Go-To Outfit Formulas for Busy Mornings

We get it — mornings can be hectic. Between making your coffee, printing lesson plans, and maybe wrangling your own kids out the door, sometimes fashion is the last thing on your mind. That’s why we LOVE go-to outfit formulas. Here are a few of our faves:

💛 Midi Dress + Denim Jacket + Comfy Sneakers
💛 Pencil Skirt + Graphic Tee + Cardigan + Flats
💛 High-Waisted Trousers + Modest Blouse + Mules
💛 Knit Dress + Belt + Slip-On Shoes + Statement Earrings

Create a few outfits in advance at the beginning of the week, or even hang a few “ready-to-go” looks at the front of your closet. You’ll thank yourself on those early mornings!

5. Dress for the Season — Without Losing Style

Classroom fashion changes with the seasons, and so should your wardrobe! But no need to buy a whole new closet. At Lena Layne, we’re all about layering and transitioning pieces smartly:

For fall, pair your summer dresses with tights and ankle boots, then add a chunky cardigan.
In winter, go for thicker fabrics, cozy scarves, and knee-length coats you can wear over everything.
Come spring, lighten things up with pastel tones and breezy tops.
And in summer, rock those short-sleeve midi dresses and flowy skirts with cute sandals.

We keep our collections updated year-round to help you transition smoothly (and stylishly) from one season to the next.

6. Function Meets Fashion

Modest teacher fashion isn’t just about looking good — it’s about making your day easier. Here’s what to look for:

Pockets! Dresses and skirts with pockets = game changer.
Stretchy waistbands that keep you comfortable through the day.
Non-sheer fabrics so you don’t have to fuss with layering.
Breathable material for those hot classroom days or recess duty.
Washable pieces — because let’s be real, glue, glitter, and markers happen!

At Lena Layne, we design with real life in mind. Our pieces are cute enough for staff meetings and practical enough for playground duty.

7. Confidence is the Key to Any Outfit

No matter what grade you teach, your students look up to you. When you feel confident and comfortable in what you're wearing, it shows — in how you teach, how you carry yourself, and how you connect with your class.

Modest fashion doesn’t mean boring or bland. It means choosing pieces that represent you while respecting your values and your lifestyle. At Lena Layne, we’re proud to help educators feel empowered and stylish every single day.

8. Treat Yourself — You Deserve It

We know teachers often put everyone else first. But this year, make it a goal to invest in you. Whether it’s a new fall capsule wardrobe, a fresh pair of earrings, or just a dress that makes you feel extra special, don’t be afraid to treat yourself.

And if you're shopping on a budget, good news! We’ve got:

Teacher discounts (yes, really!)
Weekly sales
Loyalty rewards
Bundle & save deals in-store and online

You’re shaping minds — and that deserves a little fashion love!

Here’s to a Stylish School Year

So, teacher friends, as you get ready to welcome your students and dive into another year of making a difference, know that Lena Layne is cheering you on every step of the way.

We’re here with the stylish, modest, size-inclusive pieces you need to look and feel your best — from the first bell to the final dismissal. Let’s make this your most confident, comfortable, and fashion-forward school year yet!

Come visit us in-store or shop online anytime — we can't wait to help you build the perfect teacher wardrobe. 🍎✏️💛

With love,
The Lena Layne Team

Chalkboards & Chic: A Teacher’s Guide to Stylish, Modest Fashion from Lena Layne