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 for the perfect teacher outfits!

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.

An olive green button-down shirt dress with brown flats and a statement tortoise shell necklace.

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.

This outfit features a green button-down shirt dress with a tie waist topped with a denim jacket and taupe shoes.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!

A navy dress with ruffle sleeves and brown flats finished off with a statement necklace.

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!

A chambray blazer is over a navy dress and taupe peep toe wedges and finished off with a statement necklace.

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.

A chambray button-down shirt paired with a printed skirt taupe flats and a statement necklace.

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.

This teacher outfit is a white button-down shirt topped with a green utility jacket and a printed skirt finished off with taupe peep-toe sandals.

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.

A chambray blazer tops a white button-down and navy chinos and brown flats.

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.

Alison is wearing a chambray button-down shirt with gray jeans with a skinny gold belt and finished off with taupe flats and a statement necklace.

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.

Gray jeans are paired up with a chambray button-down shirt and topped with a black and white gingham vest and taupe flats.

Chambray Shirt/Gingham Vest/Gray Jeans/Crystal Necklace

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

Your turn! What teacher outfits are your favorite?