It’s officially that time of year again — school is back! We have a full week of looks prepared for any teachers and/or office professionals looking for some new clothes to transition you from summer to fall! As a reminder, here are each of our sizing details:

ASHLEY: 5’8 | 18W/20W | 2X | 42DD

CAROLINE: 5’7 | 26W/28W | 4X | 50C

JESS: 5’2 | 16P | 1XP | 38DD

DAY 1

DRESS (2X) | OVERPIECE (2X) | SNEAKERS | TOTE BAG (SIMILAR)

ASHLEY’S THOUGHTS:

If you are looking to bring a pop of color to your classroom, this look is perfect! The dress is super comfortable and the perfect canvas to layer with lightweight patterned over-pieces like this floral one. Sneakers are great for this look to keep it casual, trendy, and offer function for days when you are on the go! The tote bag is such a classic that will transition through every season and is made to last!

DRESS (4X) | Shoes | TOTE BAG

CAROLINE’S THOUGHTS:

This was my first time trying a button-front shirt style dress like this, so I was a little nervous about the fit. I think the 5X would have been a better choice for my body because the 4X was a bit snug across my belly. Overall, I really loved the look of this outfit though! The biggest winner for me was the bag! It is so pretty and HUGE — you can fit so much in this thing! I also think an outfit like this would pair so well with a pair of classic white sneakers!

TOP (2) | PANTS (16P) | SHOES

JESS’S THOUGHTS

This look is so classic and simple! Unfortunately I found that these pants were a bit snug in the 16P but too large in the 18P for me, so it wasn’t a perfect outfit, but with the right pair of pants this one is a winner!

DAY 2

TOP (2X) | BLAZER (20) | PANTS (2X) | SNEAKERS (SIMILAR)

ASHLEY’S THOUGHTS

I seriously love these Spanx pants so much (use code ASHLEYDXSPANX for a discount), so I knew they were a perfect base for a teacher outfit. They are so comfy and easy to pair any style top with! I chose a dressier white t-shirt and my go-to camel blazer. I love how you can keep this outfit more on the professional/office side or transition it into more of a casual/on-the-go vibe all with what shoes you choose to wear! I opted for a super comfy pair of On Cloud sneakers, but this look would be great with so many different shoe options!

TOP (4X) | PULL-ON PANTS (4X) | SANDALS

CAROLINE’S THOUGHTS:

I am ALL about wearing pants that feel like loungewear to work. The key for me is a pull-on style with stretch. These are an extra high-rise style from Old Navy absolutely fits the bill. I got the 4X in these and they are a little roomy, so I probably could have done a 3X. I love how colorful and fun this top is and it’s also super comfortable. I even took one of the pink colors from the pattern and grabbed a pair of sandals that matched!

CREWNECK PULLOVER (1XP) | PANTS (16P) | SHOES

JESS’S THOUGHTS:

This is for real the cutest pink sweater! I love the oranges! It fits great and is super light weight! The pants are AMAZING and have great structure while still feeling SO comfortable. 10/10 recommend this look to all the teachers out there!

DAY 3

DRESS (1X) | BLAZER (2X) | SNEAKERS (SIMILAR) | TOTE BAG (SIMILAR)

ASHLEY’S THOUGHTS:

I love this look so much! It’s always a great idea to grab a comfy dress you love from your closet and pair it with a blazer for work! I love pairing a look like this with sneakers that give you the function and style you want when you have a job where you’re on your feet most of the day! Once again — this tote bag is such a classic that will transition through every season and is made to last!

DRESS (26/28) | OVER-PIECE (26/28) | SHOES

CAROLINE’S THOUGHTS:

This look is serving up Ms. Honey from Matilda in the best way. It made me feel so cute and ready to sit on the ground to host circle time in my fictional classroom. I love how comfy this dress is for real and it has pockets — what more can I want? The tie-front over-piece is absolutely unnecessary since this dress has short sleeves already but it’s so adorable so I love it. Shoes are the Dream Cloud line from Lane Bryant and they are the most comfy low heels I have ever worn (I hate heels).

DRESS (XXL) | DENIM JACKET (XL) | shoes | BAG | CUP | earrings

JESS’S THOUGHTS:

I love this dress. I have it in this color and the black and I wear them both ALL the time. Great quality and so so comfy! Jean jacket is such a win! Great fit and the perfect amount of stretch to make it comfy to move in!

DAY 4

TOP (2X) | BLAZER (2X) | PANTS (18) | SHOES

ASHLEY’S THOUGHTS:

I have sung these pants’ praises many time and I won’t be stopping any time soon. They are SO comfortable and make me feel so profesh. I paired them with a super cute paisley print top that is great for layering with a cardigan or blazer, like I am wearing here! This look is perfect for teachers who have parent conferences or meetings with admin!

TOP (4X) | SKIRT (4X) | SHOES | BAG

CAROLINE’S THOUGHTS:

I love this outfit so much, y’all. I forget how easy maxi skirts are - they always make you look so put together and require so little effort. I love this twist front t-shirt like top too! It gives a little extra something to a typically very plain piece of clothing. I also LOVE this bag. It is so spacious and structured - very much a modern stylish briefcase vibe.

TOP (2) | BLAZER (1) | SKIRT (2) | SHOES

JESS’S THOUGHTS:

I think this look is such a great mix of casual and professional. The top is super easy and runs generous - I can see wearing it with SO many outfits! The skirt is so cute - it runs on the larger side for me! Love this linen blazer for the warmer months!

DAY 5

TOP (similar) | BLAZER (2X) | JEANS (18) | SNEAKERS | TOTE BAG (similar)

ASHLEY’S THOUGHTS:

This is such a fun, more professional take on a casual Friday outfit! Pairing black denim with a casual, fun top and bringing in a colorful blazer? Adorable. Then adding the platform Converse sneakers? Even cuter! Added the tote bag again because how could I not??

TOP (4) | JEANS (30) | SANDALS

CAROLINE’S THOUGHTS:

I love a good classic casual Friday look! The jeggings are super comfy and easy to move around in - I sized up to a 30 and after wearing them a full day, I think I should have stayed with my regular size 28 because they do stretch a bit! I love this button-front, embroidered top with the denim! This look would be SO CUTE on a field trip - now I want to go on a field trip.

TOP (XL) | CARDIGAN (XLP) | white cami (xl) | PANTS (16P) | SHOES

JESS’S THOUGHTS:

These pants!!!!!! Omg — I love them so much. I was so happy with the fit and the length, I didn’t want to take them off. These were definitely true to size on me! The black linen vest/top is loose and comfy and SO cute, and the cardigan is a classic staple that can’t go wrong.

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