Tips for back-to-school shopping for teaching clothes + Old Navy try ons

It’s the month before school starts and you’re a new professor or TA: what are you going to wear? I remember so clearly freaking out over this question right after I moved to start my masters degree. I didn’t know what to buy before grad school and I really wished there was a teaching clothes shopping list that could solve this for me. So today I thought we could go on a mall trip and try a few things on to make some new teacher outfits!

Before you head out back to school shopping, I recommend doing a quick try-on of the clothes you already have. If you have business casual items you like, try them on to figure out if they still fit and look good. If they do, ask yourself what other items you might need to make even more outfits. Here are a few teaching clothes I wear over and over:

-Black dress pants

-A midi length shirt dress

-A white button down shirt

-A long cardigan

-A sharp blazer

-A good work bag (more on that here)

With just these 6 items, I have the ability to mix-and-match in my more casual stuff, like sneakers, jeans, and t shirts. My point is: it might feel like you need to buy an entire closet, but buying just enough to get through the first week of teaching is fine! This will give you time to reflect on how formal/informal your department is and what you like and dislike out of the items you buy.

With that in mind, I decided this week we should go to the mall together, just like old times when I was shopping for TA clothes. Today, here’s what I would try/buy at Old Navy!

I started out looking for dress pants to teach in, and man, it’s a brutal time to buy dress pants. Old Navy had approximately 4 pairs total but I made it work. This is their classic skinny dress pant, which comes in tall and petite sizes and a ton of colors online. The only thing I can say with certainty about this pant is size up a size! They run small.

Sweater (wearing a S, usually I wear a S or M in tops)

Pants (wearing an 8, usually wear a 6)

Coastal grandmother style has worked its way to Old Navy. They had a bunch of cute button downs that I was eyeing but this one was too cropped for me (fair warning I am 5’11”–I order their tall sizes online whenever possible!).

Button down (wearing a M)

Cami (this would be nice for layering under blazers)

I have to say at this point I was feeling a bit outdated in skinny dress pants, so I tried a puff sleeve top. This would be nice and light for August/September teaching.

Top (wearing a S)

If I was going to buy skinny dress pants this year I might look for a few more trendy items to update them, like an oversized sweater vest and chunky loafers!

This pair of chinos was a nice choice for the college classroom! They come in tall and petite sizes also. And the button down strikes again, this time in a light blue, which I think looked the nicest of the options.

Button down (wearing a M), also came in a non-cropped length

Pants (wearing a 6)

Next I found a stretchy midi dress and promptly wore it for the rest of my try-ons because it was that comfy. I could see this being a great layering item with button down shirts and sweaters and cardigans and blazers and boots….probably the winner of the try-on to me!

Dress (wearing a M, it is clingy so I would pick the larger of 2 sizes if you’re deciding)

What would you have picked? Where else should I go back to school shopping? 🙂

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4 thoughts on “Tips for back-to-school shopping for teaching clothes + Old Navy try ons”

  1. I am so grateful for these tips. I spent the past 2+ years in scrubs, and now that some academic activity is back on-site, I honestly found myself wondering what on earth was I wearing in pre-covid times.
    Even for someone without a teaching job, these tips were a good starting point to quell the panic buys and to provide much needed guidelines for a ‘work capsule’ of sorts.


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