Real Teacher’s Back to School Outfits and Must Haves + Giveaway!

It’s back to school month which means if you’re a teacher, it’s time to get your closet sorted and ready for work. Lucky for me, I’ve got two of the most stylish teachers I know that are regular participants in the GYPO Style Challenge and who I’m blessed to also count as friends – Gabriella and Natalie.  Today they’re sharing their favorite teacher’s back to school outfits and must-haves to get your closet ready for when school’s back in session. Even if you’re not a teacher, I know you’re going to love their style! Now let’s check out some real teacher’s back to school outfits!

Meet Gabriella

First up is Gabriella. Gabriella will be beginning her 25th year of teaching this September and has been a primary teacher in both English and French. She’s been married to her husband Thierry for 24 years and mom to Matthieu who just completed his first year of university in sciences. Originally from Ontario, Canada, she moved to British Columbia when she was 14 and loves to travel with her family.

Gabi says…

“I notice that I get the most compliments when I’m doing the Style Challenge (of course) or when I follow the rule of four. I feel most put-together yet comfy in skirts or colored jeans with a solid or patterned top and a layer like a cardigan, vest, or jacket (bomber/jean/military) and a necklace. Otherwise, when I’m in a rush to get ready, I grab a solid dress (sheaths are a breeze) and add a topper. Easy peasy in a pinch and a rush!”

Tip:  Pin this post for some back to school inspiration!

Gabriella’s Teacher Outfit Formulas

Denim Jacket + Tee + Printed Skirt + Long Necklace

Women wearing a teacher's back to school looks featuring a denim jacket, printed skirts and solid top.

Denim Jacket + Sheath Dress + Colorful Necklace

Cardigan + Printed Top + Pencil Skirt +Lace Up Sandals

Striped Top + Short Sleeved Sweater + Jeans + Riding Boots

A teacher wearing dark wash jeans with tall riding boots, a striped long sleeve top under a cream cowl neck sweater.

Striped Top + Utility Vest + Colored Denim + Printed Flats

Denim Dress + Utility Jacket + Riding Boots

Denim Jacket + Gray Tee + Red Skirt + Lace Up Sandals

Follow Gabi’s stylish teaching adventures on Instagram.

Meet Natalie

Natalie has been teaching at the same school in downtown Toronto for 16 years. She met her husband David (who is also a teacher) at the school they teach at. She currently teaches grade 4 and has taught all grades from junior kindergarten to grade 6.  She’s been married for 11 years and they love to travel and have taken time off from teaching to travel the world two times! They do not have children of their own but are lucky to have so many wonderful children in their lives.

Natalie says…

“I like to have things that all mix and match and are very simple to wear. My husband calls it comfortable elegance (sweet man). Teachers need to be able to walk, talk, interact and always look professional. I love that my students notice too – I had one sweet boy in my class last year that complimented me every single day about something different – thinking about his kind heart makes my heart swell!”

Natalie’s Back to School Must Haves

1. large tote

Here is my go-to. I have it in cognac.

[Reversible Cognac Tote]

2. Sheath Dresses

A simple dress. They can be patterned or neutral and they are easy to throw on and I truly think they look lovely on everyone. I always wear mine with a neutral cardigan. I love these ones by Leith and I have it in grey, olive and black:

[Leith Tank Dress]

3. Neutral, thin cardigans

I have them in almost every colour – but my go-to is a light linen colour.

[Long Linen Blend Cardigan]

4. Dark wash skinny jeans or slacks –

I can wear jeans to school but if I do they are always dark wash. These are my go-to jeans:

[Modern Skinny Jeans]

Here is a classic slack that I also love:

[Straight Leg Pants]

5. Blouses

Simple and classic. I have lots of colors and love the simplicity of a classic blouse with skinny jeans or slacks. Here is the Portofino from Express:

[Portofino Shirt]

6. Simple tanks

Patterned or neutral with wide shoulders to wear under cardigans or alone if my classroom gets hot! Something like this:

[Sanctuary Linen Knit Tank]

7. Crewneck thin sweater

This will be worn with slacks or dark jeans.

[J. Crew Crewneck Merino Sweater]

8. Flats

I love my Sam Edleman – but Dexflex from Payless is another less expensive option. Here are my favorite (cognac color) and they go with everything!

[Sam Edelman Felicia Ballet Flats]

9. A simple wedge heel

I need to be able to walk and to be comfortable (therefore not too high) and also stylish:

10. Jewelry

I tend to keep these fairly simple because of the dreaded lanyard that all teachers have to wear!!) But I do like to make a bit of a statement with my earrings. And my students LOVE this! They notice everything and comment every day on jewelry they love!

[Kendra Scott “Elle” Drop Earrings]

Back to School Giveaway

One lucky lady is going to win a $300 Loft gift card to get her back to school wardrobe ready + a prize pack of planners from one of my favorite brands Carrie Elle including a Grade and Record Book, a Lesson Planner, and a Password Book (you get to choose the covers for each!)

Choose one (or all) of the easy ways to enter below!

a Rafflecopter giveaway

Your turn! What real teacher’s back to school outfits were your favorite?