End of School Outfit Roundup

by - May 30, 2023


Summer break is finally here! But I've got one more round-up of teacher-approved outfits for you before things fully transition into all-things summer. Don't worry, though. A few of the things featured in this post will work through the season, and I've got two dresses I bought specifically for summer, although they could both be styled for the classroom as well. I'm all about versatility.

Sizing info: I'm 5'2" and weigh about 135 lbs. I usually wear size 6 or s/m in clothes and size 7 in shoes.


I was so excited about this skirt. It is so much fun and was the perfect accessory for my Maui and Moana unit. This is the third time I've bought this skirt - that's how much I love it. I have the dusty blue gingham and the grassgreen floral print. Both of those are shorter lengths on me, but all three are the same size (medium). The gingham is a completely different fabric; it's much thicker and a bit stiff. The waist is elastic, it has a subtle tiered design, and it has pockets, which is always a plus.

I fell in love with this t-shirt on first sight. "You can do hard things" is something my health coach would say to me in pretty much every session we had, and it's stuck with me. This shirt comes in a green color as well, and they've got a couple other sayings you can choose from. It is a fitted tee, which is why I got it in a medium.

I love these braided strap white wedges. The heel is just under 4-inches but it feels much lower to me. These are a perfect finishing touch for almost anything I would wear in warmer months. A word of warning, though. The strap is a bit tight, so if you're between sizes, you might want to consider sizing up to avoid uncomfortable squeezing.

T-shirt / Jeans / Belt / Sneakers (similar)

This year, my students were obsessed with all things emo, even though most of them didn't have a true understanding of what it means. Considering I grew up in that era and never really outgrew it, I decided to give them a glimpse of the style I always find myself falling back on.

Let's start with my belt. I can't describe how excited I was to find this. I had a belt like this for pretty much my entire teen and young adult years. I never really got into the studded belt trend, but the grommet belt was my absolute favorite.

This Kiss graphic tee was just too perfect to pass up. I had other plans for it when I bought it, but it definitely worked for the aesthetic I was going for. My black super skinny Rockstar jeans have been in my closet for so long, they're practically part of the family. My sneakers are the unr8ted brand (one of my faves because they're usually super comfortable), but I got them on clearance and haven't been able to find them online. I've linked to a pair that's pretty close, but honestly I've not seen anything that has the zipper sides plus laces. That's what made me fall in love with this pair. They're high tops, not wedge.

T-shirt / Vest (similar) / Skirt (similar, similar) / Sandals (similar)

If this outfit looks familiar, that's because I've worn and shared it before. This skirt is one of my favorites. I'm not the biggest fan of the quilt/patchwork trend except for in a skirt, and this one is a lot of fun. It's been long sold out, but I've linked to a couple of options that have a similar vibe. My vest is several years old, but you can find denim vests pretty much anywhere. My t-shirt is just a basic scoop neck that I got from Walmart. I linked to the brand, but the colors are always changing so this exact pink might not be available. My sandals are old, too, but they're still a favorite. They're an easy, neutral shoe that's comfortable and wears like flip flops without looking like flip flops.

Dress (Wantable) / Shirt (similar) / Sandals (similar)

This dress is a favorite from a past Wantable box. It's got adjustable spaghetti straps, so if I wear it for school I have to wear something over it. So far, I haven't strayed from my chambray button-up because I just really like the look. I partially button it and then tie the bottom and tuck the tail underneath. I've had mine for quite a few years, so it's no longer available. My sandals are pretty old, too, and long sold out.

Shirt (similar) / Jeans (similar) / Sandals

I'm not going to lie. This pair of ecru-colored jeans has been really difficult for me to style. I don't think it's because of the color, though. They're straight-legged but in a curvy cut, so the fit is a little off for me, I think. They feel almost baggy, and while they don't look bad, it's a definite change for me, so my mind hasn't quite wrapped around it yet. I do like this shirt paired with them, but I wish I'd done something different with my shoes. I love these sandals, but the color isn't right for this outfit. I honestly don't know what other shoes I would choose though.

Shirt (similar) / Pants / Belt (similar) / Sandals (similar)

This is another pair of pants I've struggled to style recently. This time it's because of the color. I can't decide if they're green or blue. So I've mostly been keeping it simple, which for me means no patterns. It's hard to tell in the picture, but my blouse has a lace-like pattern to keep it from being just a plain white shirt. I don't remember my reasoning for the flat sandals, but typically I would wear a shoe with a bit of a heel with this style of pants. The great thing about this pair, however, is that they're actually the right length so I can wear any shoes with them. You can read more about them and the other pants from this brand that I have here.

Shirt / Pants (similar) / Sandals (similar)

This was me coincidentally dressing in my school's colors. I mean, I knew they were our colors, but I was honestly just pairing colors that I thought looked nice together. These gold linen pants are a favorite, and every time I wear them someone inevitably asks for the link. Unfortunately, this is a tough color to match. However, Old Navy does have a pretty pale yellow pair of pants that are cut pretty similarly, so I linked to those.

My blouse is a really good one, y'all. I love the swiss dot trend. It gives any piece of clothing personality and depth. I like the split neck design of this shirt as well as the flowy sleeves. It comes in 20 additional colors.

You can't tell from this picture, but I'm actually wearing wedges. They're about 4.5 inches, too. Anyway, they're a few years old, so I linked to what I thought was a decent option.


This was my last school-related outfit. I wore this on my last official work day for this school year. There were no kids present, though. I wore this because I had an appointment that afternoon and wanted to look semi put together and not like I'd been sitting in an empty classroom for half a day. Anyway, I love literary-themed shirts, and The Wind in the Willows will always be a favorite, so I couldn't pass up this Frog and Toad graphic tee. I don't think it's a perfect match with my skirt, but it's close enough.


We've made it to my first summer outfit! I fell in love with this dress when I saw it. The bodice is smocked, which I like because it's just a flattering style. The length is appropriate for most everything. The sleeves can be worn on or off the shoulder, and as you can see are slightly puffed, which we all know I love. The pattern is perfect for spring and summer. It's so bright and fun.


I picked up this dress and sandals during Old Navy's Memorial Day sale. I got the dress in a small because the straps are not adjustable. I probably could have worn the medium, though, and I'll most likely not put it in the dryer so it doesn't shrink. The bodice is a jersey material with zero stretchiness. The skirt is polyester, I believe, and prone to wrinkles. I love the color, though.

The sandals are completely flat and nice and strappy. I'd been looking for a dark brown flat sandal like this since my other pair felt a bit dated and look a little worse for wear since they got wet not too long ago. These are nice and sturdy, so I'm hopeful they'll hold up for awhile.

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