Back to School Teacher Outfits to Wear Now and Later

by Alison Lumbatis

Like many of you, I have tons of respect for our teachers and all that they do for our kids. We are so very fortunate to have a quite a few teachers in the GYPO community. This time of the year, for all that they do, I try to make back to school an easier transition for them. One small way I can do that is by helping them out with what to wear.

Today I’m partnering with J. Crew Factory with some “wear it now” and “wear it later” looks just for our hard working teachers! If you haven’t checked it out yet, J. Crew Factory is the perfect shopping destination for teachers. Their pieces are classic, comfortable, high quality and affordable. Plus they offer a teacher discount every day! Teachers (and college students too) get an extra 15% off every J. Crew Factory purchase with a valid ID. Click here to verify eligibility and you’re good to go!

These teacher outfits do double duty for the transition from summer to fall. You can wear them now as is and add on some layers later when the temps start to drop.

Sizing Tip: All pieces fit true to size. I’m wearing a size 2 or XS in all items and am 5’4″ and 125 lbs.

Day One – Wear it Now

The only thing better than a great shirt dress is one that has POCKETS! This dress is so soft and comfortable and it doesn’t turn into a wrinkled mess when you sit down.

Utility Shirt Dress/Tortoise Link Necklace/Leather Loafers

Day One – Wear it Later

Add a denim jacket to take off the chill and up the cool. This jacket is an awesome length and hits at the right spot on the hip.

Utility Shirt Dress/Denim Jacket/Tortoise Link Necklace

Day Two – Wear it Now

The ruffled sleeves on this dress are all the embellishment it needs. Add a necklace and flats and ta da! Instant outfit. You’ll want more than one color!

Ruffle Sleeve Dress/Tortoise Link Necklace/Leather Loafers

Day Two – Wear it Later

Dress it up with a chambray blazer and crystal statement necklace. This look is perfect for picture day!

Ruffle Sleeve Dress/Chambray Blazer/Crystal Necklace

Day Three – Wear it Now

This fun pleated floral skirt is just right with a super soft chambray button down. This is my favorite chambray shirt EVER! The fit is perfect.

Chambray Shirt/Floral Skirt/Crystal Necklace

Day Three – Wear it Later

Swap the chambray for a white oxford shirt and layer up with a cotton utility jacket.

Cotton Pocket Jacket/White Oxford Shirt/Floral Skirt

Day Four – Wear it Now and Later

This outfit already has double duty built right in! Just take off the chambray blazer on warmer days – a white oxford shirt and navy pants always look sharp.

Chambray Blazer/White Oxford Shirt/Navy Pants/Tortoise Link Necklace/Leather Loafers

Day Five – Wear it Now

Casual Friday calls for soft chambray and denim. These gray skinny jeans fit great and are oh so comfortable with just the right amount of stretch to keep their shape.

Chambray Shirt/Gray Jeans/Crystal Necklace

Day Five – Wear it Later

Just add a quilted gingham vest for instant warmth and style! This one isn’t too bulky.

Chambray Shirt/Gingham Vest/Gray Jeans/Crystal Necklace


J. Crew Factory is having a back to school giveaway of $2500 in cash! Enter here through August 9th, 2018 at 2:59 a.m. ET.

Big thanks to J. Crew Factory for sponsoring this post and making it easy and affordable to go back to school in style!

Getting my pretty on with Mom with Style, Style Assisted, Dawned On Me, Style-Splash, Shelbee on the Edge, Walking in Memphis in High Heels, Shopping My Closet, Glass of Glam, Straight A Style Blog, Posh Classy Mom, Fashion Should be Fun, High Latitude Style, Pocketful of Polka Dots and Style Elixir.


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