Real Outfit Roundup: Summer to Fall Style

by - September 29, 2020


Fall may be officially here, the first month of fall in the south tends to be more of a transitionary period. We frequently have days in the 80s followed by a day or two in the 60s. And the humidity comes and goes. That makes getting dressed in early fall a little tricky, and more often than not I find myself mixing my summer clothes into my fall/winter wardrobe.

I've tried to do a better job over the last few weeks of taking photos of my actual outfits. Seeing as I have 16 outfits to share with you, it appears I didn't miss many days. This edition of Real Outfit Roundup is a mix of old and new pieces, and because we have moved into a new season some of the summer styles are no longer available, but as always I'll link to similar items.

If you're a regular reader, you'll have seen a few of these outfits in previous posts. I rarely style an outfit solely for the purpose of a blog post, unless I'm showing how to wear one particular thing multiple ways. Most of these have also made an appearance on my Instagram page.

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

navy striped shorts

I truly don't remember the why behind this outfit. I'm pretty sure it's from before school started back, but I can't tell you if I even left the house that day. I can tell you that I picked these shorts up back in August, but they do still have most sizes and they're marked down. I sized up to an 8 because this brand tends to run tight in shorts.

Outfit Details
Shirt: Amazon (exact, wearing size M in white)
Shorts: JCPenney (exact, wearing size 8 in navy Jenny stripe)
Shoes: Old Navy (similar)

embroidered shirt

I wore this outfit to a business meeting and then to my dad's birthday dinner. I bought this shirt in late spring, and it didn't come in until right before my surgery so it hasn't seen much wear. It's great quality, though, and surprisingly still available in limited sizes. My jeans are from a couple years ago, but I'll link to some similar pairs in different washes below.

Outfit Details
Shirt: Old Navy (exact, wearing size M)
Pants: Oldy Navy (similar, similar, similar)
Shoes: Target (similar)

plaid dress combat boots

This dress has already been featured on the blog, with three other ways to style it through the cold weather months. Click here to read the post. That said, I did actually wear this version for a full day.

Outfit Details
Dress: Target (exact, wearing size L)
T-Shirt: Amazon (exact, wearing size M)
Boots: ShoeDazzle (similar)

gold striped tshirt

I wore this to a fish fry for my brother and dad's birthdays. It was an attempt to dress like fall without dying in summer temps. Unfortunately, everything in this outfit except for the sneakers is old. I did, however, link to a pair of really good white cut-off denim shorts and a pretty similarly-colored striped shirt below.

Outfit Details
Shirt: Target (similar)
Shorts: Walmart (similar)
Shoes: Old Navy (exact, wearing size 7)

striped dress denim vest converse

The next three outfits were all worn during the week I distributed the September magazine. They also were all featured in a post last week talking about how to layer casual dresses for the transition into fall. Click here to read the post.

Outfit Details
Dress: Old Navy (old - similar)
Vest: StitchFix (old - similarsimilar)
Shoes: Converse (exact, wearing size 7 in athletic navy)

black dress utility vest

Outfit Details
Dress: Forever 21 (old - similarsimilar)
Vest: JCPenney (old - similarsimilar)
Shoes: Old Navy (exact, wearing size 7)

tank dress white denim jacket

Outfit Details
Dress: Walmart (old - similarsimilar)
Jacket: Walmart (exact, wearing size M)
Shoes: Academy (old - similarsimilar)

braves tshirt

Did you guys know I'm a baseball fan? I grew up watching the Braves, and although I don't watch them play often these days, I still keep up with their season. So when Old Navy put all their MLB t-shirts on sale for $10, I couldn't pass it up. It's so soft it's like it's already been lived in. I've worn it three times since it came in, so roughly once a week.

Outfit Details
Shirt: Old Navy (exact, wearing size M)
Shorts: Walmart (similar)
Shoes: Converse (exact, wearing size 7 in athletic navy)

hello sweatshirt

I love this sweatshirt so much, you'll see it in this post twice. The first time I wore it, I paired it with my favorite denim shorts (that are no longer in stock, and I refuse to link to a subpar pair) and leopard sneakers. It was one of those days where the wind was cool but the sun was warm, so I compromised. Anyway, this sweatshirt is ridiculously soft. It's not oversized but it's not fitted.

Outfit Details
Sweatshirt: Old Navy (exact, wearing size M)
Shorts: Target
Shoes: Academy (similarsimilar)

tie dye tank top boyfriend jeans converse

I wore this on our anniversary. We got Chinese take-out and had a picnic lunch. It was one of those perfect early fall days, where I was perfectly comfortable in a tank top and jeans. These jeans are going to be my go-to this fall and winter, I can just feel it. They're a little loose on me, but I can't tell if it's because I've gotten smaller or because of the boyfriend cut. My tank top isn't available in this exact pattern anymore but it is available in a bunch of others, which is why I still linked to it.

Outfit Details
Shirt: Old Navy (exact, wearing size M)
Jeans: Old Navy (exact, wearing size 6)
Shoes: Converse (exact, wearing size 7 in athletic navy)

short sleeve henley

This is not the best picture, and normally I wouldn't bother to include it, but I really wanted to share this short-sleeved henley with you. I've worn it several times already but I keep forgetting to take a picture. This is such a good basic. It's a step above a plain t-shirt so it doesn't feel too plain if you wear it on its own, but it's also perfect for layering underneath a sweater. It comes in two other colors.

Outfit Details
Shirt: Old Navy (exact, wearing size M in raspberry sorbet)

jogging pants sailor moon tshirt

I shared this picture on Instagram so people could see the reality of trying to work at home on a day when school has been canceled. If you can't tell, I was barely hanging onto my sanity. Anyway, these cargo-style joggers are only available in limited sizes, so I also linked to a similar style. My exact Sailor Moon shirt isn't available anymore but there are tons of them out there, so I linked to three that I liked.

Outfit Details
Shirt: Target (similar, similar, similar)
Pants: Old Navy (exact, wearing size M in Lost at Sea Navy, similar style)
Shoes: Converse (exact, wearing size 7 in athletic navy)

purple floral dress

Words cannot express how much I love this dress. I love the loose fit, the slightly ballooned sleeves, the visible black stitching, and the fun colors. Typically in this brand I size up, but I didn't have to with this dress. I don't know how consistent the sizing is so you might want to try before you buy. I paired them with my lace-up black booties because I wanted that feminine touch that combat boots just don't provide.

Outfit Details
Dress: Target (exact, wearing size M in black/purple)
Shoes: ShoeDazzle (exact, wearing size 7)

hello sweatshirt

A sweatshirt so nice you're seeing it twice, only this time with black jeans and wedge sneakers.

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

pink sweatshirt

I've had this sweatshirt since the beginning of the year but they keep restocking it in pretty similar shades of pink. It comes in a bunch of other colors too. It's thin, which is great for southern fall/winter.

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

long sleeve striped dress

This dress is several years old, but Old Navy keeps bringing the style back year-after-year with different patterns. There is a striped version that is the reverse of this one, along with a leopard print, two floral patterns, and solid black. These boots were one of my best purchases last year, but they're not available this year. There are two kinda similar styles in the same color that I'm linking to below. I find Old Navy's shoes to be true to size.

Outfit Details
Dress: Old Navy (exact, wearing size M)
Shoes: Old Navy (similar, similar)

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