What to Wear When Fall Feels Like Summer

by - October 29, 2020


Does it feel like fall where you live? Down here in the South, it definitely does not. We got that nice little tease at the beginning of October, and then it was right back to upper 80s and humidity. Even for us, it's been above average temperatures for this time of year. A cold front is moving through today, though, and next week is looking much more seasonable. I might even get to wear a sweater or two.

The question is how do you dress for fall without dying in the summer-like heat? The answer is actually pretty simple: it's all about the colors and textures. Instead of pairing your favorite skirt with a light-colored top, switch it out for something darker. Trade your denim shorts for boyfriend jeans, distressing optional. Swap out your sandals for sneakers, or booties if you can stand it.
Need some examples? Let's dive into our Real Outfit Roundup!

Sizing: I'm 5'2" and typically wear size 6 or medium in tops, size 6/8 in dresses, size 6 in pants/skirts, and size 7 in shoes.


pink striped tank bf jeans

This tank top doesn't scream fall, does it? I wore this on a really busy Monday, and by busy I mean work busy. It was one of those days where I was glad I set my afternoon alarm, otherwise I would have been late picking Alexis up from school. Anyway, while this pink and white striped tank top isn't what I would call a fall shirt, pairing it with distressed boyfriend jeans instead of a pair of shorts and then grounding the outfit with these neutral taupe sneakers makes it feel more seasonally appropriate. My tank is currently on sale for under $10 and comes in several other patterns/colors.

Outfit Details
Shirt: Old Navy (exact - wearing size M)
Jeans: Old Navy (exact - wearing size 6)
Shoes: Old Navy (exact - wearing size 7)

striped dress

This dress is such a nice transitional piece. The olive stripe makes it feel more late summer early fall than Spring to me, and the thicker, almost rough material adds a nice fall texture. I haven't had a reason to wear these chunky heeled olive sandals this year, so I threw them on to run to the post office, and then immediately regretted it as my ankle was still healing. My dress is on clearance for under $25 and still available in all sizes (10/29). My sandals are the Universal Thread brand from Target if you want to look for them secondhand.

Outfit Details
Dress: Old Navy (exact - wearing size M)
Shoes: Target (old - similar)

rust floral skirt olive tee

This is going to sound so crazy, but two days later I had to go back to the post office, except this go 'round I went to a smaller one that's actually closer to my house, and I think it'll be where I go to actually mail things from here on out. Anyway, you've seen this skirt several times on the blog, but up until now I've been pairing it with lighter colors. To make it feel more fall appropriate, I paired it with an olive green t-shirt, which matched the leaves in the pattern nicely, and then grounded it all with my taupe sneakers.

Outfit Details
Shirt: Target (old - similar)
Skirt: Amazon (exact - wearing size M)
Shoes: Old Navy (exact - wearing size 7)

polka dot shirt black jeans

Fast forward to the next week. I really wasn't feeling it on Tuesday. I hadn't been sleeping well, had a bunch of work to finish for the upcoming November magazine, and a parent-teacher Zoom meeting. Of course, that was the day my hair decided not to cooperate at all, so ignore it. Anyway, this knit button-up shirt has become my go-to for when I want to look more put together but stay comfortable. I decided to keep everything kind of monochromatic and paired it with black skinny jeans and sneakers. It felt almost like athleisure, except with jeans, and I can see myself repeating this with joggers in the future.

Outfit Details
Shirt: Old Navy (exact - wearing size M)
Jeans: Old Navy (exact - wearing size 6)
Shoes: Walmart (exact - wearing size 7)

joggers camo shirt

Speaking of joggers...the next day I was so freaking tired, and had a bunch of editing to do, as well as helping launch a sister magazine's website. It was one of those days where I started working as soon as I got home from dropping Alexis at school and worked right up to my alarm to go pick her up. Days like that call for comfort, so joggers and a soft t-shirt was the order of the day. I threw on my white denim jacket because I felt like my overall outfit was way too dark.

Outfit Details
Shirt: Old Navy (exact - wearing size M)
Jacket: Walmart (exact - wearing size M)
Joggers: Old Navy (exact - wearing size M)
Shoes: Walmart (exact - wearing size 7)

striped tshirt orange skirt

The next day, my to-do list was much lighter, and I was feeling all the fall vibes, so I cautiously pulled this orange skirt from my closet. I haven't worn it in awhile because of that recent health problem, but to my delight it fits again! I absolutely cannot remember where I got it from, and I cut the tag out a long time ago because it was scratchy, but it's several years old so I know it's not available anymore. Paired with a black-and-white striped t-shirt and black sneakers, it became the perfect fall outfit. I knotted my t-shirt because it didn't look good left untucked or tucked in.

Outfit Details
Shirt: JCPenney (old - similar)
Skirt: (old - similar)
Shoes: Walmart (exact - wearing size 7)

blue floral skirt feather tshirt

I'm kind of on the fence about this outfit, even though a lot of people told me how much they liked it when I posted it to Instagram and shared on my Facebook page. I know the coloring of the t-shirt works but I'm not sure if I really like the big feathers combined with the small floral print of the skirt. It's almost like there's too much negative space between the feathers and the skirt. I'm probably overthinking it. Anyway, I wore this on Monday and didn't go anywhere other than the after school pick-up line.

Outfit Details
Shirt: Aeropostale (old - similar)
Skirt: Amazon (exact - wearing size M)
Shoes: Old Navy (exact - wearing size 7)

floral maxi slip dress

I wore this on Tuesday. After running a couple of errands in the morning, I took my husband to his outpatient procedure and then proceeded to wait in my car for a couple of hours. I love layering simple t-shirts underneath slip dresses to give them a little more depth. Must be the 90s kid in me. If you're looking for some good basic t-shirts that don't cost a fortune, these ones by Amazon are really good.

Outfit Details
Dress: Shein (old - similar)
Tshirt: Amazon (exact - wearing size M)
Shoes: Old Navy (exact - wearing size 7)

plaid dress over black tshirt

The plaid dress is back on the blog, but this time instead of layering it over a white t-shirt, I layered it over a black one, and instead of combat boots I finished things out with black sneakers. This is actually what I wore yesterday. I had several errands to run, and it was really warm and humid ahead of the latest hurricane headed our way (that's why my hair looks like a lion's mane). My exact dress is sold out in most sizes online, but I linked to it anyway in case any come back in stock, plus a long-sleeved version.

Outfit Details
Dress: Target (exact, long-sleeves)
Shirt: Target (old - similar)
Shoes: Walmart (exact - wearing size 7)

cow skull shirt red utility skirt

That brings us to today! This actually wasn't my outfit choice for the day, but what I the shirt and jeans I had originally picked out just didn't vibe well together, and I'm actually thinking of exchanging the shirt for a different size. So I changed into this cow skull t-shirt, but didn't like it with the black jeans. I stripped them off and this utility skirt caught my eye. The color perfectly matches some of the shading in the flowers, and this outfit was born!

Outfit Details
Shirt: Aeropostale (old - similar)
Skirt: (old - similar)
Shoes: Walmart (exact - wearing size 7)


*This post contains some affiliate links.

You May Also Like

0 comments