Best Teacher Clothing that is Stylish, Comfortable, and Professional
Whether it’s back to school time or the middle of the year, sometimes a new teacher outfit can give us just the pick-me-up we need. Today I’m sharing the best teacher clothing that will meet your school’s dress code while still making a good impression.

(This post contains some affiliate links at no cost to you!)
Best Teacher Clothing – our favorites
Okay, teacher friends, let’s jump in!

Best Teacher Clothing – Dressing for the Future
You’ve probably heard someone say that it’s important to dress like the job you want to have. The same is to be said about the teaching profession. If you aspire to be in administration, make sure you are dressing in business casual or more professional pieces whenever possible. Pairing a cute teacher t-shirt with a blazer is also an excellent way to accomplish a fun yet professional look.

One of my favorite teacher dresses is the yellow one shown in the photo above. It’s a maxi style and the bright color is usually complimented when I wear it. I wore it to a speaking event once and afterwards one of the attendees told me they had all nicknamed me Belle. As a Disney adult, I couldn’t think of a better compliment! Ha! I couldn’t find the one I had on anywhere, but I’ve linked a different one that has great reviews.

Best Teacher Clothing – Interview Clothes
If you really want to impress, men can consider a nice sport coat. For women, I think a black skirt with a teacher t-shirt and blazer is perfect. You could pair some nice tops with dress pants if dresses are not your thing.
Be sure to check the length if you are wearing a shorter dress. Sometimes the dress appears longer when I’m glancing down than it does in front of a mirror. In my opinion, you want your skirt to be right above the knees to maintain a professional and work-ready look.
It might sound silly, but the pencil shoes I’m wearing above are such a fun conversation starter. Principals usually love seeing a little of your personality while still looking work-appropriate. Those pencil shoes are no longer available, but I have a friend who painted some for herself. I think these yellow ones would work great!
Best Teacher Clothing – Casual Fridays & Graphic Tees
Do you have casual Fridays at your school? I see so many of my fellow teachers excited about this day. I’m more of a comfy dress girl but I do love the option of throwing on a pair of jeans when it’s freezing outside.

I see so many adorable teacher outfits over on instagram. If you’re looking for cute teacher clothes, that’s a great place to get some inspiration. I’d love for you to follow me there! That’s where I am typically the most active when it comes to social media.

Elevate Teacher Shirts – USE CODE HILARY FOR A 20 PERCENT DISCOUNT!
I’m a presenter for Elevate conferences and they have some absolutely adorable teacher t-shirts. Each summer they release so many new designs at Berteau & Co. I find that all of their products are extremely high quality. They have the softest sweatshirts, nice planners, and notebooks. You’ll love shopping there for plenty of teacher needs. I honestly think their prices are already great but combine it with code HILARY to really snag deals!
Amazon Teacher Shirts
I love how you can almost always count on Amazon giving us some options for free shipping. I have an Amazon credit card that also helps me save. I only use that credit card for Amazon purchases, but you receive quite a bit back to spend on their site.

I also love grabbing some from Amazon. Not everything in our closets has to be name brands, right? How cute is the one shown above? I love the 90’s throwback on this one. Just a tad of leopard print mixed in… adorable!

I really love the wording on this yellow one. They have other color choices but this one is so cheery and fun!

Bows are all the rage right now. In fact, my oldest daughter told me she wanted all of her back to school accessories to be bows and pink themes. We love the pencil bows. How cute would this be paired with those pencil shoes I mentioned earlier? LOVE!
Best Teacher Clothing – Jean Jacket

A good jean jacket is an absolute must in your teacher wardrobe. One of my favorite pairings is to add a little bit of color with a denim jacket on top.
This one with pearls is one of my favorites. My middle school daughter has loved it so much that she actually has it hanging in her closet now and I have to borrow it from her!
BEST TEACHER CLOTHING – HEADBANDS & OTHER ACCESSORIES
Throwing on a headband is such a great option when you’re having a not-so-good hair day.

How cute is this TEACH headband? It’s a statement piece all in itself and your students will love it!

Who can resist this adorable pencil headband? The price point is fabulous too!
Best Teacher Clothing – Weekend Vibes

I HAD to share this link to my favorite athletic pants. Remember when leggings were all the rage? Well, these are looser and so much more comfortable but they still feature a cuffed leg area. Not so tight but oh so comfy! I love to wear these on the weekend because of the waistband and pockets. I liked them so much that I ended up ordering two more pairs in that same black color. I travel a lot to present for school districts and at conferences and these make the perfect airport outfit.
Best Teacher Clothing – Favorite Stores
Next, let’s look at a quick roundup of some of our favorite stores and what we recommend snagging from each one to build a fantastic teacher’s wardrobe.
Old Navy

Who doesn’t love Ann Taylor Loft
Ann Taylor Loft is another teacher favorite. Make sure you let them know you are a teacher! They offer a 15% teacher discount on full price clothing purchased in store. You’ll just need to show your valid teacher ID at checkout. Every teacher (and adult) should have a really nice pair of black pants. I also love to keep black jeans on hand too. Did you know that they are two different distinct lines now? Loft was an extension of Ann Taylor, but now they are two separate brands with the same parent company. Ann Taylor is an excellent choice for your staple pieces offering a professional and sophisticated work wardrobe. Loft offers a more casual. and comfortable style. Don’t sleep on JC Penney! I’ve found some really nice shirts for my husband there. Male teachers can find great deals on a nice dress shirt or some basic tees in different colors. I’ve actually found really comfortable shoes for my kids and myself there. JC Penney is a great place to stop at right before a new school year. I’ve found some really great jeans at the Banana Republic Factory Store. This is another great place to look for classic pieces, such as black dress pants. NY & Co is another teacher favorite. NY & Co stands for New York & Company. You’ll find blazers with just enough color to add quite a bit of interest! I love an a-line skirt from there or their maxi dresses. Some of their dresses are more suited to an evening event or low-cut, but I’ve found plenty of work-ready longer dresses to add to my wardrobe. Plus size teachers should be able to find choices at all of the stores listed above, but you may find your next pair of favorite pants or a new top at Lane Bryant. This store was created specifically for plus size women so they tend to offer a range of choices for a variety of sizes from 10 to 40. I spotted some absolutely adorable sweater dresses and belted dresses on their site. Looking for more fun ideas? Maybe you’re ready to dress up like Johnny Appleseed or a Chicka Chicka Boom Boom tree? Happy Teaching and Parenting this week friends!

JC Penney
Banana Republic Factory Store

NY & Co.

Lane Bryant


