Teacher Style

Hello teachers! I have styled dozens of teachers, school staffers, and social workers over the years. No matter the job, the body shape, or the budget, the wishes are always the same: you want to look stylish and pull-together but comfy so you can move around all day. Here you'll find a compilation of great pieces and ideas that to get you started.

"Finds" is where each individual item lives. Depending on your view via laptop or phone, the outfit combinations can be found in "looks" or "look book" section.

Click on an individual item for closer details or simply click through to head straight to the retailer. Anyone can leave a comment below the items if you have an idea or question for me. Feel free to write your name or just leave it as "guest".

Need dressier ideas? More casual? Different style? If you need more personalized style advice, please email me at jaime@jaimediehlstyle.com and I'll let you know how we can work together for your specific needs.

Xo, Jaime

Tops

13 Items

Some items I link may earn a small commission, which supports my business!

shop.nordstrom.com »
factory.jcrew.com »
jcrew.com »
  • Jaime on Sep 3, 2019

    40% off as of 9/3

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amazon.com »
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  • Jaime on Sep 3, 2019

    Excellent layering basic, great price. Comfy, they wash well and they come in packs... around 6 bucks a piece!

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factory.jcrew.com »
  • Jaime on Sep 3, 2019

    I have the black and white version of this, it has a super flattering neckline and a slimming cut on the short sleeves. It's a great basic!

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shop.nordstrom.com »
  • Jaime on Aug 17, 2019

    This top has the comfort and versatility of a tee shirt but the cute sleeves give it something extra.

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factory.jcrew.com »
factory.jcrew.com »
shop.nordstrom.com »
shop.nordstrom.com »
  • Jaime on Aug 12, 2019

    I always have teachers looking for red school colors, this one is comfy!

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express.com »
  • Jaime on Aug 12, 2019

    The Portofino. The ultimate work blouse that I recommend across many professions if you like button-downs that are fluid.

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express.com »
  • Jaime on Aug 12, 2019

    The Portofino. The ultimate work blouse that I recommend across many professions if you like button-downs that are fluid.

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express.com »
  • Jaime on Sep 3, 2019

    Great sale as of 9/3.

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Bottoms

13 Items

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oldnavy.gap.com »
  • Jaime on Sep 5, 2019

    also got this pair *destructed wash, love these too!

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oldnavy.gap.com »
  • Jaime on Sep 5, 2019

    These two distressed pairs are certainly not recomendations for the classroom- just wanted to link you to a VERY popular and budget-friendly weekend option.

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oldnavy.gap.com »
  • Jaime on Sep 3, 2019

    Great price, great fit! Non skinny fit, from IG stories.

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gap.com »
factory.jcrew.com »
factory.jcrew.com »
  • Jaime on Sep 3, 2019

    extra sale

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athleta.gap.com »
  • Jaime on Aug 21, 2019

    #1 for comfort! Read the 2,000+ reviews, everyone dresses these up AND down. The 32" inseam is their regular length, this is going to be good for 5'4 ish people and a slight heel. The petite is 29" so that would be for 5'4 in flats, much more petite (5'2 and under could use a small heel). Their long is 35".

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oldnavy.gap.com »
  • Jaime on Aug 12, 2019

    Fun Fall color! These are best selling pants. They come in regular, tall, and petite and they're stocked every year in a variety of colors.

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shop.nordstrom.com »
oldnavy.gap.com »
  • Jaime on Aug 12, 2019

    Best selling pants! They come in regular, tall, and petite and they're stocked every year in a variety of colors.

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shop.nordstrom.com »
  • Jaime on Aug 12, 2019

    Mid-rise slim boyfriend if jeans are allowed. One of my most-loved boyfriend jeans, 9 out of 10 women LOVE these.

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athleta.gap.com »
athleta.gap.com »
  • Jaime on Aug 12, 2019

    Don't let the sneakers on the model fool you! These pants can be dressed up as well. These pants are a HUGE winner for so many levels of work attire from super casual to business casual.

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Shoes

12 Items

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birdies.com »
shop.nordstrom.com »
shop.nordstrom.com »
rothys.com »
  • Jaime on Sep 3, 2019

    Super popular brand for teacher comfort but it's an investment for some... they don't work for *some* but the positive reactions overwhelm.

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lulus.com »
justfab.com »
factory.jcrew.com »
zappos.com »
zappos.com »
zappos.com »
factory.jcrew.com »
  • Jaime on Sep 3, 2019

    I am often asked how to wear flats but not "appear" short. If you're petite but MUST wear flats, try to avoid rounded toes. These J Crew flats are my go-to and the shape of this toe- box elongates the leg, it continues the sight line you draw with your leg, instead of cutting-off the line with a round toe-box.

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shop.nordstrom.com »

Layers

12 Items

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factory.jcrew.com »
  • Jaime on Sep 3, 2019

    Colorful sweaters are an excellent way to liven up the wardrobe. Big, drapy cardigans are nice and all but not everyone is seeking to coverup (aka overwhelm) their frame.

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factory.jcrew.com »
shop.nordstrom.com »
factory.jcrew.com »
factory.jcrew.com »
factory.jcrew.com »
shop.nordstrom.com »
nordstromrack.com »
shop.nordstrom.com »
shop.nordstrom.com »
oldnavy.gap.com »
factory.jcrew.com »
  • Jaime on Aug 12, 2019

    A yearly favorite! This baby is back again and I have yet to see a client turn it down.

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Etc

12 Items

Some items I link may earn a small commission, which supports my business!

factory.jcrew.com »
kendrascott.com »
lulus.com »
  • Jaime on Sep 3, 2019

    3 colors, not too short, cute Back to School night piece or other special work-related function.

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nordstromrack.com »
justfab.com »
zappos.com »
  • Guest on Sep 5, 2019

    Thanks!!! I’ll look for burgundy or leopard! Great idea!

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factory.jcrew.com »
  • Jaime on Sep 3, 2019

    This is a great piece for administrators or those who like to have an elevated piece on hand for Back to School Night or a more special work event.

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factory.jcrew.com »
factory.jcrew.com »
factory.jcrew.com »
amazon.com »
  • As an Amazon Associate I earn from qualifying purchases.

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oldnavy.gap.com »

How To Style Your Pieces

25 Looks

Just added this pop of color 9/3! Comfy flats- people are very opinionated of their Rothy's- must-try for yourself!

When jeans are allowed in the workplace, wear a dark wash and they shouldn't be distressed. Try to follow the "3-rd piece rule" when wearing jeans... use a top and a layer to add polish.

Athleta for the win, worth the investment since you can use them for work or weekend. They go with blouses, sweaters, and cami/blazer combos.

Teacher wish: style PLUS comfort! This goes-with-everything shirt has the comfort of a tee but the universally flattering boat neck gives it a polished feeling. Add a skirt (or fun printed bottom) and add a layer, outfit complete!

There are 3 key ingredients to bring your Summer dresses into early Fall: tights, booties, and a layer to bring it all together.

This outfit work really well for those of you who like a one-and-done piece but still want to feel stylish and pulled-together. Note: this dress could be a tad overwhelming on petites.

These pants are comfy but professional, a common request... and the color is great for Fall. Don't be afraid of this color, you can style it with black, navy, heather grey, chambray.

When styling red (or in this case brick red/burgundy) I like to add two more colors out of white, black, and heather grey. It may be just me but when I wear red with ONLY black, it's a 1990s flashback... and not the good kind.

What's not to love? This t-shirt dress offers both style AND comfort and I bet it won't last long! Stylist tip: you don't have to wear the belt where the belt loops are. Take those belt loops off, you don't need them once you own the dress. Tie at your natural waist or swap out for your own belt.

Client-favorite black skinnies, loose blouse and comfy blazer for a chic and classic ensemble. These specific skinnies are 28" so these are ankle length on 5'4-6 ish. Please reach out for more personalized recommendations.

Casual Friday? Still looking pulled-together here!

Authoritative and professional yet relatable... nice idea for the middle grades.

I have MANY clients who dress up these pants, don't let the sneakers on the model deter you from giving them a chance!

If you're allowed jeans but hate feeling too casual, try dressier flats and go with two pieces up top to feel more put-together. Styling suggestion: half-tuck this top and add a long necklace.

I have MANY clients who dress up these pants, don't let the sneakers on the model deter you from giving them a chance. Follow my style suggestions and you're golden!

Of course, it depends on each school's dress code but these shoes and pants are made for all-day comfort. The stripes are so cute with the olive bottoms and the cardigan comes a few different pops of color. If you can get away with these shoes, you can prevent being underdressed by having two coordinating pieces on top rather than one casual piece. The stripes add visual interest and you can swap the cardigan for a denim jacket as well. Styling suggestion: half-tuck this top and add a long necklace.

This is a good mix for the beginning of school and early Fall. A denim jacket works here as well. Lots of my Kindergarten and younger grade teachers enjoy casual dresses like this with tights and booties.