8 Casual Outfits to Transition to Fall

by - September 06, 2022

Back to school has always been the unofficial signal that fall is just around the corner. Add in the fact that Labor Day is celebrated as the last hurrah of summer, and it's time to start thinking about autumn fashion choices. But if you live in an area that doesn't see fall temperatures until Halloween at the earliest, dressing for fall is easier said than done. Luckily for you, I am an expert on the month-long transition period from summer to fall-ish.

For me, it's all about color, shoe choice, and strategic layering that doesn't add any actual warmth to your outfit. I'll show you what I'm talking about in this edition of real outfit roundup featuring eight outfits I wore to work. For those of you just tuning in, I just started teaching seventh grade English Language Arts, so my weekday style is a direct reflection of that - professional but casual and easy to move around in.

Sizing note: I'm 5'2" and weigh about 145 lbs. I typically wear size small or 6 in clothing and size 7 in shoes.

Shirt (similar) / Jeans / Shoes

You really can't go wrong with black and white, no matter the season. This knotted tee is one of my favorites. It works with jeans or leggings and would probably work with a pencil skirt. Unfortunately, this specific shirt is no longer available, but I linked to one that's almost an exact match. Loafers are trending these days, although I don't think they ever went fully out of style. This pair has a cute little chain detail on the tongue and a chunky sole. They've got about an inch-and-a-half heel so they're not flat but low enough to be comfortable all day.

Shirt (sold out) / Jeans / BeltShoes

This blouse is so cute, y'all, but it's not available anymore. It's hard to tell from this picture, but it's a dark green color. It's got a darling Peter Pan collar and buttons all the way up. It's pretty loose but will easily tuck in and has a flattering drape when half tucked. I paired it with my plain black skinny jeans and kept my shoes simple with these black flats. These come in a lot of colors and are pretty comfortable for the price.

Shirt / Vest (sold out) / Skirt (similar) / Shoes

This was my attempt to show school spirit without wearing jeans and a t-shirt (all my school shirts were dirty and I didn't feel like doing laundry the night before). I really love this style of skirt, and the yellow t-shirt helps to show off the yellow in the floral pattern nicely. I added the vest because I felt like it needed something extra. A vest is a great transition piece to add a layer when it's still too warm for a jacket.

Shirt / Pants (sold out) / Shoes

These pants, y'all, are the absolute best. However, I have a really hard time finding the right tops to pair with loose pants. I think a graphic t-shirt would probably work, but I decided to keep things simple with this pretty black blouse. It's got a lace yoke and decorative buttons. I kept my shoes simple and comfortable with these black flat-form sandals. Sadly, my pants aren't available anymore, and I couldn't find anything similar.

Shirt (similar) / Jeans / Shoes (similar)

Flares are back in style, and I am so here for it! These maroon flares are giving me all the heart eyes. I decided for this first go round to keep things simple with this cream-colored lace blouse. I did have to opt for heels since I'm short and needed to have some height to keep the bottoms from dragging the floor.

Shirt / Skirt (similar) / Shoes

This skirt should be familiar to you since I wear it all the time. For this, I decided to keep things really simple and chose this lavender t-shirt to complement the purple tones in the floral pattern. I chose these braided sandal heels to elevate things a bit (my feet did not thank me the next day).

Shirt (Wantable) / Pants / Shoes

These navy blue pants are another of the Old Navy OG Chinos, and they're just as good as the others I've shown on the blog. I topped them off with this pretty embroidered blouse I got in my Wantable box, then finished things off with my star sneakers. They didn't really match, but I needed comfort over style this particular day, so it is what it is.

I had a professional development workshop this day, so I got to dress down. I'd been dying to wear this coffee t-shirt with my floral combat boots, and since this was the first day of September, a.k.a. the beginning of fall, I figured this was the perfect time. The boots are from the kids shoe section at Target. I wear size 5 in little girl shoes.

You May Also Like