Back To School Teacher Outfits With J.Crew Factory

Happy hump day! School starts here one week from today! I can not believe it. With that being said, I always get asked to share some back to school teacher outfits.

I have so much respect for teachers, they have a hard job, and I definitely think it’s a calling to be a teacher.

I am not a teacher, but I have friends that are teachers, and my daughter is a teacher by profession (although she stays home now with her two children), and she approved of these outfits.

Several pieces are basic wardrobe pieces that you can mix and match with other pieces you already have in your closet.

With each outfit, I’m wearing the Zoe suede d’Orsay flats. It seems most teachers I talk to like to wear flats because they’re on their feet all day.

First up, for the teacher that likes to dress with some flair, I’m styling the printed Jamie pant. These pants feel like pajamas!

They’re so comfortable and believe it or not they have an elastic waistband in the back. Yes, please! These pants run large, size down one size.

Back To School Teacher Outfits With J.Crew Factory

I added a chambray shirt that will be perfect when the weather turns cooler. Right now you could wear these pants with a short-sleeve shirt.

Back To School Teacher Outfits With J.Crew Factory

Chambray popover shirt (I’m wearing an XS)/Printed Jamie pant (I’m wearing a size 4)//Zoe suede d’Orsay flats (TTS)//Necklace//Earrings//Black Satchel

If the printed pants are too much for you, they also come in olive, black and navy.

Back To School Teacher Outfits With J.Crew Factory

Chambray popover shirt (I’m wearing an XS)//Jamie pant (I’m wearing a size 4)//Zoe suede d’Orsay flats (TTS)//Necklace//Earrings//Black Satchel

I thought this Tortoise link necklace was cute and a great staple piece to wear all year.

Back To School Teacher Outfits With J.Crew Factory

A shirt dress is a perfect back to school outfit. I’m not sure about the length, but I’m 5’6″ so consider that. This dress is cute and comfortable.

Back To School Teacher Outfits With J.Crew Factory Back To School Teacher Outfits With J.Crew Factory

Button-through shirtdress (I’m wearing a small)//Zoe suede d’Orsay flats (TTS)//Necklace//Earrings//Black Satchel

When the weather gets chilly or if you get cold like me in the air condition, add this sweater blazer.

Back To School Teacher Outfits With J.Crew Factory Back To School Teacher Outfits With J.Crew Factory

Sweater Blazer (I’m wearing an XS)

Lastly, an animal print blouse with a black skirt. The black skirt has an elastic waistband. It doesn’t get much more comfortable than that!

Back To School Teacher Outfits With J.Crew Factory Back To School Teacher Outfits With J.Crew Factory

Long-sleeve tie-neck top (I’m wearing an XS)//Wool-blend sidewalk skirt (I’m wearing a size 4)//Zoe suede d’Orsay flats (TTS)//Necklace//Earrings//Black Satchel



I think any teacher would look cute and stylish with these outfits!

Thank you for taking the time out of your day to stop by my blog. I’m also on FacebookPinterest, and, Instagram.

Beauty For the Heart~~Praying for all the teachers as they head back to school. Praying for: Protection, Patience, Confidence in Teaching, and a love for the students they teach.

In everything make yourself an example of good works with integrity and dignity in your teaching. Titus 2:& (HCSB)


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  1. I was a teacher 20 years ago… seems hard to believe it’s been that long! I love that little chambray dress.

  2. While I’m not a teacher, I think anyone would look great to wear these suggestions and yes prayers for our teachers everywhere.

    1. Good morning, Cyndi!🙋🏻‍♀️

      Always, thank you for sharing!
      I’m an early childhood educator, Spanish and music teacher. I go back to work after Labor Day. My husband and I ( he enjoys going shopping with me)😊 went to Nordstrom, Macy’s and Talbots and bought several outfits in petite size.
      Have a blessed day!

  3. Very fun outfits for teachers or anyone! I love the chambray dress, it’s so cute and the sweater blazer is perfect with it! Praying for teachers everywhere to have a fantastic school year with their students!

  4. I’m not a teacher but I am a professional and I like these outfits. I don’t think I could wear the dress at work though because the sides may be a bit too short. Very cute though!

    1. I agree with the skirt and dress being too short, unless you are wearing tights or leggings. You have to consider what could be seen when going into a sitting position or leaning on a desk or squatting to speak to a small child.

  5. Love the outfits and your hair. What color are you using on your hair? I would love to have my hair like yours.

  6. Cute outfits for school! I’m a Montessori teacher assistant and we are on the carpet a lot and like to wear comfortable clothes. The Jamie printed black & white pants are $29.00, I also like a bargain! JCrew also offers a teacher discount:). Thanks Cyndi😀

  7. Yes! Great teacher outfits! Both of the trouser outfits are perfect. I tend to sit on the floor a lot with first graders, so rarely wear a dress. Thanks Cyndi!

  8. I would not like that chambray shirt due to the wrinkles created where you’ve bent your arms. The last outfit looks nice for a busy office worker! But I can’t wear skirts to work so I’d switch it out for pants. Nice post, though!

    1. Loved the teachers outfits very cute and comfortable pray for our teachers in this time with our country in such a mess. Cindi you always look great in anything you put on love all the leopard and camo this fall.

  9. I was a teacher for 31 years and these outfits are perfect for the classroom. As for wearing dresses and skirts to school, I learned a long time ago that wearing biker shorts under a dress or skirt always worked for me. I learned this after a fire drill…I ran out the backdoor of my classroom, the last in line behind all the students, my feet went out from under me and I rolled down a hill, and yes, I was wearing a dress that day!

  10. Loved, loved, loved these outfits! I am now retired from teaching , but this post is perfect for teachers! Trendy, tasteful and appropriate! I can also see these outfits in a lot of business professions. Thanks Cyndi for helping us always to look our best!

  11. I’m not a teacher, but I would likely wear some of this. The first outfit is super cute and I would wear that to work as well as the denim dress. The comments that these aren’t your style I agree with, but I’m pretty sure you even mentioned that yourself :). I just think we aren’t used to seeing you in flats. Good job with a post that is out of your comfort/style zone!

  12. I Love these outfits we don’t have a dress code here in our schools and you can’t tell the teachers apart from the parents the way they dress, which makes me wish at least the teachers had a dress code, they are the ones who are suppose to be setting an example for our kids. If I could I would share this post with all the teachers here so at least it would give them a idea of how they should dress. Thank you for the post

    1. I know exactly what you are talking about.
      I always try to dress professional. I keep in mind I may have to meet with the Superintendent.

  13. I think the concepts of the outfits were good but, the fit seemed off on almost every item. Everything looked over-sized on you except the denim dress. Do you usually wear petite’s? How tall are you?

  14. The shirt dress might be long enough for my 5’2” frame. And I loved the sweater jacket…can’t decide which color to get! Not a fan of the others.

  15. Thank you for doing a teacher edition! I work in the school system and love new ideas! J. Crew factory is one of my favorite stores! They offer great prices on stylish pieces!

  16. I truly appreciate your Beauty from the heart today! You look nice in your pictures but as a PreK teacher, I rarely wear a skirt or dress as I’m often up and down on the floor or in small chairs. Most of the time I wear blue or colored jeans and never heels. The green pants you styled look cute and comfortable.

  17. Thank you for the teacher prayers! We all need them, especially in this day & time when we are expected to raise these students as our own! I love what I do, but it can be very stressful! I loved the Olive pant pics. It’s really hard to wear a dress to school with all the hands on, engaging projects and aactivities our students are doing these days! Keep on praying!

  18. i love this post. these are some great outfits. also find it very interesting that Jolynne shane took a poll and I asked for teacher outfits and here they. i interview for a job last week as a assistant in prek. 🙏🏼i get it

  19. I was a science teacher in the public school system, and on lab days I never wore anything that I couldn’t spill on. Sometimes wore lab apron, as lab coats were too hot.
    Now I teach some college English classes, I can finally wear dresses and skirts! I love the leopard skirt and the chambray dress. Don’t love the fit of the pants, although the idea of the outfits is cute!

  20. Thank you for remembering teachers! The style ideas as well as the prayers are soooo appreciated! I am a newly retired teacher so this is the first time in 35 years that I will not be heading off to first grade! Finding a “new normal” and I’m excited to hear God’s plan for my next steps!

    The last 2 outfits are my style to a “T” ! And, I would wear either in my new “job” as well! 💕

  21. Hi Cyndi!
    Thanks so much for all you do! I love getting your emails and seeing all of the outfits that you showcase. I also love hearing about your life as it reminds me that you are a real person.
    I am a teacher and I love the idea of wearing the denim dress (I teach high school). However, I am not loving the animal print for school. In fact, I find animal print in general very uncomfortable to wear. It always looks great the way that you style it I just find that for me, it feels ‘cheap’ when I wear it. Or that I should be wearing it for an evening outing. Any suggestions to get over that?
    It really helps to see all of these ideas. Please consider some other options for teachers as I truly respect and admire your work. Thanks again. Blessings

  22. I love your outfits! I’m interested in the J Crew Factory Outlet Sweater Blazer. Did you find it ran TTS? There is not a store close to me so I can’t try them on. Reviews say I’m between Small and Medium….thank you.