Teacher Style: Tips for Dressing Professionally

Guest blog by Sarah Sides (aka @schoolinstyle)

It’s no secret. Teachers don’t make a lot of money. But I have good news. You don’t have to bring in a six-figure salary to look polished, professional, and feel good about yourself! Sarah from @schoolinstyle here sharing a few of my tips, tricks, and hints to help you show up to school every day in style!!



1. Invest in a few essentials. In my opinion, a good teacher wardrobe includes the following: a pair of black pants, a pair of good quality everyday (non-athletic) leggings, white sneakers, a white tee, dress shoes (heels or flats, your preference), a neutral-colored jumpsuit, a flowy dress, a fun graphic tee, a chambray button-down, a jean jacket, and some cardigans. It’s not always about the amount of clothing you have, but instead how many different ways you can style them! Which leads me to my next tip...


2. Mix and match what’s already in your closet! Think outside the box! Knot a dress to transform it into a top, turn a jumpsuit in a pair of pants, or add a tee over a dress to give the dress the illusion of a skirt. The possibilities are endless! Layering is your friend...and not just for warmth, but to give each piece a whole new look! I enjoy the challenge of trying to come up with new ways to wear existing pieces.


3. Cute and comfortable are not mutually exclusive events! (I teach math...can you tell?!) Comfy can be cute, just as cute can be comfy! Lucky for us, there are plenty of “work pants” that include an elastic waistband! I don’t know about you, but I’m sure glad to live in a world with elastic waistbands, especially after gaining the Covid10. 😬 I’ve linked a few of my favorite work pants with elastic waistbands here. The best part? They are all affordable. One pair could even be delivered to your doorstep in just two days! 😉


4. Flowy is your friend! I think there has been a longstanding belief that dressing professionally includes pencil skirts, fitted sheath dresses, and high heels. While I love all of the above in moderation, you can utilize other items to dress professionally and still be crazy comfy! Shift dresses are some of my favorites. Flowy tops are all the rage. However, as a general rule: one flowy piece per outfit. Pair a flowy top with tighter pants, or looser (wide leg) pants with a more fitted top. But of course, rules can always be broken! That being said, one piece of advice I’d give to teachers entering into this profession is this: dress ultra professionally for interviews, first days of school, and/or anytime you’re around parents (PT conferences, Back-to-School Night, etc.) Wear said pencil skirts, sheath dresses, and heels. Buy a blazer. First impressions are everything, and my belief has always been this: dress professionally to be treated that way.


5. You don’t need a ton of money to look polished! Almost every article of clothing in my wardrobe (shoes included) comes from one of the following retailers: Target, Old Navy, Amazon, and even Walmart! Walmart has upped their game big time over the past couple of years (the Time and Tru brand is 👌🏻)! Additionally, wait. for. sales. Never do I ever buy anything full price from Old Navy because they have sales (up to 50% off) so often! Target doesn’t offer quite as many sales, but they will occasionally have a promo for 20-30% off or BOGO 50% off. Now, I know some people would argue that clothing from these retailers isn’t as sustainable as the more expensive stuff, and I totally get that. I’m someone, however, who enjoys quantity over quality. Trends change so much and so quickly that I’d prefer to spend less money on an item so that when it fades out of style, I don’t feel as guilty. But again, personal preference!


6. Look for inspiration everywhere! No joke, the other day, I saw a girl in Costco wearing a cute outfit...a black and white striped dress, with a white striped sweater over the top. Would I have pieced together two such items on my own? Heck no! But I loved it on her, and decided to wear it for myself! (I have only tried it on at home, or else I’d share my picture.😊) I have also taken inspiration from t.v. shows (ahem, The Bachelorette), from a pair of earrings, and from my own students! One additional note: you don’t have to own exact items to recreate an outfit! You may already have something similar in your closet, or if not, your favorite influencers--myself included--will often link similar items for your shopping convenience. (Liketoknow.it is a free app that makes shopping super easy!)


7. Accessorize! I know it sounds simple, but a pair of earrings or a stack of bracelets can really supplement a look! I love me some leather earrings from Nickel & Suede because they make a bold, but lightweight, statement. And it wouldn’t be 2020 without mentioning the most trend-worthy accessory of the year - face masks! I love matching my mask to my outfit. My favorite masks come from (shocker) Target and Old Navy! Add a mask lanyard to ensure you never misplace it!


8. Don’t be afraid of spirit days!! (Okay, this may not be a “Tip for Dressing Professionally” but it’s worth mentioning.) What other job encourages their employees to wear pajamas to work? Plus, engaging in spirit days allows your students to see a different side of your personality, and it’s a great way to show them how much you love your job! My favorite spirit week ever involved dressing as a different decade each day (90s // 80s // 60s // 50s // 2020 VSCO girl)!


9. Spruce up your spiritwear. I’m not a plain t-shirt kind of girl. I would 100% prefer dressing nicely to wearing a school spirit apparel. But, I also enjoy supporting my high school’s team! So I find ways to incorporate school spirit into more polished-looking outfits: add a flannel around your waist, wear a cardigan, dress the colors. Once again, be creative! Here, I styled one tee in 12 different ways!


10. I’m going to leave you with this: find what works for you and stick to it! Just because it’s trendy, or looks great on someone else, doesn’t mean you’re going to love it on yourself. For instance, pleated skirts are not for me. I adore them on other people, but I’ve come to accept that they’re just not right for my body type. Regardless of how trendy they may be, I don’t wear them. On the other hand, I am a huge lover of heels. Some women may refuse to wear heels, no matter what, when, or why, and that is okay! Find your own style. Wear what you feel good in. Because let’s be honest, aren’t we all a little happier when we like our outfit?!



Be sure to follow along on Instagram (@schoolinstyle) for teacher style, teacher life, shopping deals and sales, motherhood, and a whole lot more!


This post contains commissionable links. That means that when you purchase an item through a link I have provided, I make a very small commission at no additional cost to you. Thank you!



Sarah Sides is in her 14th year as a high school math teacher on the Kansas side of KC. Although math is her first priority in the classroom, she also has a passion for fashion. She loves proving to others that you don’t have to spend a fortune to look good, and loves showing her (female) students that, despite common stereotypes, beauty and intelligence can go hand-in-hand. Sarah is also blogger and mama to three boys. 


©2019 by The Modern Principal. Proudly created with Wix.com