Style + Casual Fridays, + Work

Wednesday Outfit: Back to School, Literally

Next week, my Sister-in-Law is going back to work as a teacher after a multi-year hiatus.  She’s excited, and nervous, and wondering what the classroom will be like post-pandemic (ish).  But we’re trying to make sure at least her wardrobe is on point.

I went on a search for teacher-style blogs and influencers, and came across this photo, which I thought was a cool look.  So let’s recreate this outfit from @my_teacher_style for those who like a more relaxed work outfit.

Jacket // There were several choices for the blazer here, but I went with J.Crew’s Parke blazer because I like a little more structure.  There is also a looser, more relaxed version.  Both of these styles come in plus and petite.

T-Shirt // I love a cool graphic tee, but I had some trouble finding one.  You see, I have one rule: I don’t wear concert tees unless I’ve been to the show.  So all the cool vintage concert tees are off limits for me.  Instead, I chose this J.Crew Factory tee with dogs on it.  I also love the Re/Done tees, but that price for a tee is a little more than I can stomach.

Jeans // I chose to go with the lighter wash for these, but to pull up with a more bootcut style.  I don’t like the Mom-jean look, it’s not flattering on most women, and I see no reason to push it.  These ‘Ab-solution’ bootcut jeans are awesome and flattering, and affordable (also in petite).

Wit & Wisdom really is a good denim line for something in a more affordable price range.  It also offers a plus and petite range.  So until I know how much baby-weight is leaving, and how much is staying, these are my go to jeans.

Accessories // I think that CALPAK Haven bag from this morning would be a great teacher work bag.  Spacious and versatile, but you don’t need a yak to carry it.

I also darkened up the mules because white shoes are not my jam.  And, of course, there are always Rothy’s if mules aren’t for you.

Lastly, I added some pink blue-light glasses for color.  They pull from the pink hues in the shirt.  And I chose these funky triangle hoops with white enamel accents.

Styling // I think a low bun would be cool with this outfit.  It balances the studious professional with the graphic tee vibe.  But down and loose is nice too. Lastly, I toss on a sheer lip color for a bit of pop.

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  1. Mandi says:

    I think it’s a cute look, but maybe a graphic tee without alcohol would be more appropriate 😉 I wanted to add that a friend who teaches 1st grade loves wearing Birdies to work!

    August 17, 2022/Reply
  2. Pam says:

    Adorable look! Love the camel mules

    August 17, 2022/Reply
  3. Nadine says:

    This is cute! I definitely need more supportive shoes to teach in. Most of my friends who teach the youngest grades insist on wearing their hair up to reduce the risk of lice.

    August 17, 2022/Reply
  4. Amy says:

    I beg to differ on Mom jeans. I was so pumped for them to come back around! #1- the comfort!!!! But, as a runner, my biggest (proportionately) body part is my quads and skinny jeans just made them feel so front & center. Most jeans hug my quads and are loose everywhere else, drawing the eye straight to… mid-thigh. Not cute. Plus , with a fitted top, everything just feels so tight. Mom jeans give the quads some room and fit snug around my waist- a much more flattering look. Surely I’m not the only one??? Where my athletic ladies at???

    August 17, 2022/Reply
    • elle says:

      Commenting just to agree with you- with athletic legs and a smaller waist I’m here for some high waisted mom jeans. They don’t look good on everyone- but no jean does!

      August 17, 2022/Reply
      • Belle says:


        August 18, 2022/Reply
    • Michelle says:

      Is there a brand you recommend? I just don’t own jeans (or any pants really) since they don’t fit. Although I have both larger thighs and hips so I don’t know if mom jeans will work either.

      August 18, 2022/Reply
      • Amy says:

        I’ve been really happy with anything labeled as a “90’s jean” on J Crew

        August 18, 2022/Reply
    • Anna says:

      I’m waiting for the super unflattering, literal 90s mom-look to transition to a just a more relaxed cut. The ones in this photo aren’t terrible, though ankle jeans just make my legs look stubby, but yeah, the very high-waisted, sometimes pleated, wide, ankle-cut does no one any favors. That said, a looser fitting, mid to higher rise, thicker denim could look good on a lot of women and avoid the sausage casing look of some skinny jeans.

      August 18, 2022/Reply
  5. Cait says:

    Thank YOU for not pushing the mom jean. Mom jeans look good on literally no one!!! Maybe on a toothpick-bodied person. But even then, I can’t help but think “you’d look much better in a different style.”

    August 18, 2022/Reply
    • Emily Davis says:

      It’s so true! The only thing sadder than people wearing mom jeans is that they think they look good. They’re SO unflattering. There is not one person on the planet who looks good in them. This is a hill I’m willing to die on. 🙂

      August 18, 2022/Reply
  6. Candace says:

    Love the overall look but as a school administrator, I’d send any teacher to change who came to work with alcohol on their t-shirt. Many districts also don’t allow jeans unless it’s a special day like spirit wear. Just a word of caution to check with your boss before you come to school on dress code for staff as there is a wide range of appropriate depending on the district and teaching assignment.

    August 18, 2022/Reply
    • Jenn S. says:

      I’m not an educator, but I clearly recall from my public K-12 days that teachers never wore jeans except for occasions like what you describe. I don’t take issue, but the type of place which may have a dress code that villainizes tank tops (not that yours does! it’s just a thing) may well.

      August 18, 2022/Reply
  7. Jenn S. says:

    I love the look (though agree that the cocktails thing isn’t situationally appropriate). I need a light blazer, sigh.

    One thing that struck me, though – what grade are we talking? I’d be terrified of a white blazer with littles, especially one that can’t be machine washed (important to acknowledge that I am neither teacher nor parent so its abstract to me and maybe I’m making a mountain out of a molehill). I’d think its fine for older kids who are less accident prone / have more awareness.

    August 18, 2022/Reply
  8. Allison says:

    It would change the colorway, but the apple tee would be perfect for a teacher, which I am (high school), and I could definitely wear this outfit if I swapped trouser jeans for the light wash.

    August 18, 2022/Reply
  9. K1900 says:

    I think the age she’s teaching matters as well. My kids are elementary school aged and the teachers seem to tilt toward more comfortable “stretchy” clothes, probably because there’s more bending, sitting on the floor, etc., so it’s more tunics and leggings. This would be super in middle/high school.

    August 18, 2022/Reply
  10. Lydia says:

    High school teacher here. Love the look you have illustrated here. My workplace is super casual and most colleagues wear jeans and tees, though maybe more ironic graphic tees for the teens to dissect! Lots of women wear breezy and comfy dresses, or straight leg jeans, and runners. Some people dress up a bit more, but it’s usually a bit eclectic or sporty casual. I mostly shorter skirts — I’m 5’4 so I can pull off shorter skirts or dresses. I find Longer skirts can look good with cool sneakers as long as it’s intentional otherwise it can read retro teacher on me! I usually wear black straight jeans (on the rare days that I wear pants— I love skirts, what can I say— but I just purchased bootcut darker blue jeans and I’m wondering how much I should shorten them as they are a bit long? Also, the bootcut jeans are a tighter fit everywhere but the lower leg. Is that how they should fit? I’m used to looser pants and jeans and due to weight loss, I’m figuring out new proportions. Thank you for the refreshing content.

    August 18, 2022/Reply
  11. S says:

    Maybe I just got lucky with one pair, but I really like FRAME jeans lately.

    As an athletic legged human, I’m hoping for a true comeback of the trouser jean!

    August 18, 2022/Reply
  12. D says:

    I’m not a teacher but I think you just created my fall outfit formula! Thank you!

    August 22, 2022/Reply