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How to Dress as a Teacher

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Show Notes:

I learned the hard way about why it’s so important to think through what we wear to school. In fact, this story is so embarrassing that I can’t believe I’m actually going to tell it to you... And, I’m only telling you this story because you might be making the same mistake I did without even realizing it. πŸ˜‚

I think I was in my 3rd year of teaching full time, and I was teaching 2nd grade. My principal was very straight-laced, very sensitive, and actually quite shy to be a principal, and he seemed like he was nervous all of the time.

One morning, he looked even more uncomfortable than usual when he asked if I would come and see him in his office.

As he closed the door, his face was all red, and he was really jittery and acting really weird and I could tell that there was something going on, but I didn’t know what it could be. Then he blurted out, clearly just wanting to get this over with,

“Um, there’s probably no easy way to tell you this. I just got a call from one of your students’ parents.”

My blood pressure immediately went up, and based on the way this guy was sweating, I braced myself, and I started to get really nervous.

He said, “They told me that one day at school you were wearing a skirt that was above your knees, and apparently, when you got up from your chair after reading your class a story, their son got quite an eyeful.”

I looked down at the skirt I was wearing, which was, of course, above my knees, which was not only common but in style for women my age, and I was horrified.

I know this sounds so crazy and so dumb now, but it never would have occurred to me that 7-year old kids would even try to look up my skirt. I was always really careful about stepping around kids who were on the floor, and I certainly wouldn’t expect kids to go home and tell their parents about it, even if they did get a peek when they shouldn't have....

I never did find out which of my students had told their parents this, but I went out that evening and, because I still loved all of my short skirts and I didn’t want to stop wearing them, I bought myself several pairs of black lycra bicycle shorts AND a couple of pairs of knee-length black leggings.

The next day, when I wore one of my skirts, I wore my new leggings underneath it. You should have seen my principal’s face when he saw me in yet another short skirt - but he was visibly relieved when he saw the leggings

So, that was my big eye-opening moment when I knew I needed to think a little more creatively about how to still look cute and be comfy, but also remain professional.

This week, I’m going to share with you what my key staples were in my teaching wardrobe and how having these staples allowed me to plan out what to wear for the entire week in about 15 minutes every Sunday night. Yes, it's true!

Once you have a few key staples in your teaching wardrobe, it’s so easy to put together outfits that will not only help to get you the respect you deserve from parents and from your principal, but that really do make a difference to how you feel throughout the day.

Please note: I will earn a small affiliate fee for any purchases made with these links.

Staple #1:
Monochromatic Leggings and T-Shirts:

First, find your perfect pair of leggings and then pair them with matching t-shirts as a simple base for an outfit, and then layer with a colorful tunic (see below) or sweater.
I bought two sets of these in black, two sets in grey, and two sets in tan or taupe.

You could also do navy or dark brown, but choose colors that provide a good base and go well with pretty much any other color, and avoid patterns. Keep it simple.

Staple #2: Brightly Colored Tunics and Oversized Sweaters:

Because I always had a monochromatic base to my outfit with black or grey or taupe, I could purchase pretty much any colored or patterned tunics or long sweaters I wanted to pair over my leggings and tank tops.

This also allowed me to put together outfits so quickly and easily because a patterned tunic with vibrant colors could be worn with any of these base colors pretty easily.

Also, comfy, oversized sweaters with handy pockets that were super cute could easily pair with any of these base colors as well.





Staple #3: Comfy Blazer in a Couple of Different Colors 

On days when you want to look a little more professional, nothing dresses up a casual look like a cute blazer, and they can be super comfortable if you buy them in soft materials. 

These look great when you wear them with a pair of skinny jeans so you can feel like you're not overly dressy but still comfortable.


Staple #4:
Super Comfy Shoes (Flats)

Although I’m the first one to fall in love with cute sandals, nothing beats a comfortable and well-made pair of flats or ballet shoes for teaching.

What I love about flats is that you can sit cross-legged on the floor with your students and still be comfortable, and treating your feet well will help your legs to not feel nearly as tired after standing for so much of the day.

If you’re going to splurge on any part of your wardrobe, let this be it – you will be so grateful that you did!


Staple #5: Teaching and School T-Shirts

Teacher t-shirts are all the rage now, and you can get so many cute styles for special occasions throughout the year that (as long as your school allows t-shirts), these can become a fantastic staple of your wardrobe when paired with a pair of leggings. 

Also, I’ve seen more and more schools encourage both teachers and students to dress in school colors and to wear school t-shirts, so find out if this is considered appropriate dress at your school, especially for an easy casual Friday option!


Staple #6: Dresses with Leggings Underneath & a Bright Sweater

I LOVED this look to get extra wear out of my summer dresses, especially during the fall and early spring months.

Simply pair any summer dresses you have with some leggings and maybe even a pair of cute boots and a matching cardigan for a fresh look!

(This dress comes in SO many cute colors & patterns on Amazon)


Staple #7: Long or ¾ Length Maxi-Skirts & Jean Jackets

I love this cute & casual look of a simple and comfy maxi-skirt, paired with a basic white tee and a jean jacket (or, if your school doesn’t allow denim, a simple black cardigan).

Maxi skirts allow you to avoid all the drama that I experienced with my mini-skirt – though of course, the fancy bicycle shorts-under-layer trick is still always an option for you… πŸ˜‰


Staple #8: Silver and Gold Accessories

Now, this is where the professional touch comes in.

When it comes to jewelry, I always wore silver or gold and bought a few different designs in chunky styles so that I could mix things up depending on which tunic or sweater I was wearing.

But honestly, these choices can offer such a variety of combinations that I think you’re going to be surprised by how many different outfits you can put together, just from these simple choices.

When it comes to shoes, I always chose super comfy ballet flats in either one of the neutral colors to match my leggings and tank tops, OR in silver or gold.

Now that we’ve talked about some of the choices you’ll want to make, let’s also talk about some of the clothing choices you’ll want to avoid.

Clothing to Avoid:

  • Shirts that show your chest or your cleavage (do the bend over test in the mirror to see if you’re okay)
  • Long necklaces (that can get caught on EVERYTHING)
  • Short skirts (you already know why... see story at the beginning!)
  • Scarves (for the same reason. Mine got slammed into my classroom treasure chest one day, much to the delight and amusement of my students, which left me momentarily suspended mid-air. My neck hurt for about a week after that but I’m sure my students still talk about it)
  • Off-the shoulder tops (probably not allowed with your school’s dress code)
  • Tank tops (worn without a sweater, at least, which can be too “revealing”)
  • Personally, I avoided white most of the time…Why? Because so much of elementary school involves snot, glitter, and paint on a regular basis, and it only takes one of your students wiping their nose on your white leggings to understand why you might not want to do this.

    It kind of makes you question your career choice, right? πŸ˜‚

So, those are my suggestions for how to put together your teacher wardrobe on a budget, and once you have the items I’ve suggested, you’re going to find planning your outfits for the week SO much easier and quicker so that you can focus on all of the other things that matter so much more!

I hope you have a wonderful week exploring some awesome, new outfit options for your teacher wardrobe. If you have any other great ideas, please comment below to share your thoughts!

πŸ’› Lori

Dr. Lori Friesen | Beginning Teacher Mentor

Creator of the R.E.A.D.Y. for School Academy, Dr. Lori Friesen has mentored thousands of beginning teachers across the country through her workshops and courses. Host of the popular podcast, Beginning Teacher Talk, and creator of the innovative literacy program for 1st and 2nd grade, Dogs Help Kids Read and Succeed, Dr. Lori is dedicated to serving educators and inspiring learners. Learn more at and at

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