What I Wore Lately: Back to School Edition

by - August 24, 2024


School is back in session, and I've got eight classroom-approved outfits for you. It's still unbearably hot where I am, and my classroom air conditioner is struggling, so you definitely will not see any fall-specific clothing pieces in this roundup.

These outfits technically go back to before I had to report for pre-planning, but they are all outfits I have worn and/or would wear to teach in.

Sizing info: I'm 5'2" and weigh about 140 lbs. I usually wear size 6 or s/m in clothes and size 7 in shoes.

T-shirt (similar) / Skirt / Sandals

I technically didn't wear this to school. However, I have worn pretty much this exact outfit, minus the sandals, to teach in before. This was the weekend before preplanning started. We went to a nice lunch and then did some final back-to-school shopping.

This skirt has made lots of appearances on the blog over the last year. It's one of those that can be easily styled for every season. It has an elastic waist and is lined. The only thing it doesn't have is pockets.

My t-shirt is just a basic t-shirt that I picked up at Walmart. This specific one is no longer available, but I'm linking to a similar one for you.

My sandals are still going strong. I like how they lightened up the dark pattern of the skirt here. It's a nice bit of juxtaposition. I sized up a half size because the straps were too tight/narrow, which is saying a lot since my feet are really, really narrow.


This is also an outfit that I didn't technically wear to teach in, but it's one that I will absolutely repeat at some point. I actually had to make a court appearance so I wanted to be dressed professionally. I was done much earlier than expected, so I ended up going and working in my classroom since I was in town.

These pants are really lightweight, but I did still get hot, which should be expected in 100-degree weather. The waist is a wider smocked band than I was expecting. They do have pleats at the hips/thighs, which make them feel fancier. They're wide legged and long enough that flat shoes will be a bit of an issue for me.

This blouse is so pretty an a perfect match for the green shade of the pants. The one thing about the blouse that drives me nuts though is the length of its v-neckline. It's about an inch too long for me, which makes it tricky to tuck into bottoms nicely. You'll notice that I've got it bloused out a lot in this outfit to compensate for it.

Dress (similar) / Sandals

I've had this Chaps dress since my days at the TV station. It's technically just a t-shirt dress, but it's such good quality. Unfortunately, it's been long sold out, but it's still a favorite of mine. I wore it on one of my preplanning days. This is one of those dresses that I reach for when I don't know what to wear, but it always looks very intentional.

My sandals are from a couple of years ago, but they're still available in this and other colors.


This is one of my favorite dresses. I wore it for Alexis's open house, which was also a preplanning day. I love it so much that I own it in two other patterns. This is the size small, which fits but pulls a bit at the buttons on the bust. The other two I own are the medium and I like the way they fit at the bust much better. This dress has a smocked waist and functional buttons from bust to hem. It's almost fully lined -- the liner ends around my knees. The tie is just for decoration.

Blouse (similar) / Pants / Belt / Shoes (similar)

I wore this for my school's open house. These are the same pants I showed in my teacher try-on haul. As predicted, they stretched out the longer I wore them, so I say to definitely get your regular size.

I found my blouse on a clearance rack at Cato. I love all the details on it, from the pretty floral pattern to the square neckline and lace trim. It's a nice light linen material so I stayed fairly cool all day.

My heels are a few years old and not really "in style" anymore, but I love them so I keep wearing them. They're also fairly comfortable for being on your feet a long time.

Blouse (similar) / Skirt / Shoes (similar)

This was my first-day-of-school outfit. How cute is this skirt?! This is another Cato find. It has a matching top, but I don't really do matching sets and didn't like how boxy the blouse was. This skirt has such nice details. I love the little pom-poms on the hem and the lace trim on the bottom tier. It's hard to see here but there are lace-like cut-outs all throughout the skirt, which is fully lined so no worries about it being see-through. The only thing it doesn't have is pockets.

I decided to let the skirt be the star of this show, so I kept everything else simple. My blouse is a year or two old. It's got decorative buttons and a bit of lace detailing at the neck for interest, but otherwise it's just a basic black top.

My strappy sandals have about an inch block heel to give me a bit height. I actually had to size down in these to a 6.5 because the straps were way too loose. I'm pretty sure I got these on clearance, but the same brand has a pretty similar pair that I'm linking to. I've not tried them on, though, so I have no idea if the sizing is the same.

Jumpsuit / T-shirt (similar) / Shoes

This was what I wore on day two of teaching. I shared this jumpsuit earlier this summer, but it's definitely styled differently here. Last time I wore a sleeveless white tank top underneath it and sandals. This go 'round, I decided to be a bit more colorful with a basic yellow t-shirt to pull out the yellow in the pattern.

My feet were hella sore from standing all day the day before (I've gotta get used to that again), so I decided to go with my backless white sneakers. It's been awhile since I wore these, and unfortunately by the end of the day I had a huge blister on one of my pinky toes. I think it's probably because I haven't worn structured shoes in three months.

Blouse (similar) / Skirt / Belt / Shoes

Day three of teaching fell on our first Friday. We get to wear jeans on Fridays, but honestly, it's still too hot for me to even think about jeans, especially since my classroom's air conditioner is just not getting the job done, so it felt like the right time to break in this denim skirt (first featured in my teacher try-on haul a couple weeks ago).

Let me start by saying that I'm glad I sized up in this skirt as it did not stretch out much at all throughout the day. It's a very sturdy denim with relatively no stretch, which has more benefits than not losing its shape the more you move around. The lack of stretch also means that the functional buttons don't gape, which is always a concern with this style of skirt. I've seen loads of maxi denim skirts, sans buttons but with a large front slit, and I just feel like those aren't really practical for teaching. This button-front alternative feels like a nice nod to the trend, and it's honestly a style of skirt that I love and have loved for years. Oh, bonus -- it has back pockets to help give some definition.

My blouse is a few years old. It's hard to tell in this picture, but it's got a peter pan collar and an understated puff sleeve. My belt is also old, as are my flats, but both are still available.

You May Also Like

0 comments