Summer to Fall Outfits (15 of my Recent Real-Life Looks)
September is here and with that our weather here in Northern NY has cooled down drastically. We have still had some warmer days, but the majority of the days have been in the 60 and 70s which means I am starting to pull out my fall wardrobe.
I’m really loving the trees beginning to change colors and the cool breeze and I am getting SO excited to pull out my jeans, clogs, socks, sweaters and all my favorite fall layers again. Here are some of the early fall outfits I’ve worn so far in September, with lots of easy, casual, and comfortable outfit ideas for those in-between days when summer is ending and fall is beginning.
I will link all of my outfits below each photo, and I do use affiliate links. This just means I earn a small commission if you purchase something (at no additional cost to you) and I so appreciate your support! Thank you!
I love “sweater and shorts” weather! This is a cotton sweater and these are linen blend shorts so I’m super comfy
outfit linked HERE
You’ll see a lot of my denim shirt(s) in this round up and all of my fall outfits. They are such a staple wardrobe piece for me!
outfit linked HERE
I decided to try these barrel jeans last year and I ended up loving them. I was excited to pull them back out this year.
outfit linked HERE
I love a black and denim look. it just always works for me!
outfit linked HERE
This midi skirt (it’s a maxi on my because I’m petite) is one of my favorites. I wear it in all 4 seasons!
outfit linked HERE
I love these pants so much. They’re comfy, make me feel like a cool mom, and so easy to wear! I also have them in green.
outfit linked HERE
I love these wide leg Gap jeans so much! They’re so comfy and mold to your body as you wear them. They come in petite, regular, and long too (I’m wearing petite).
outfit linked HERE
This skort is mom friendly and adorable! I have loved wearing it this last half of summer and I know I’ll be excited to pull it back out again next spring/summer.
outfit linked HERE
This lace skirt is my take on the fun sheer lace skirt trend. It’s fun, it’s comfy and it’s so cute!
outfit linked HERE
I bought this denim dress last year, so it’s older, but Old Navy has one almost exactly like it (with patch pockets). It’s such a staple piece for me! So cute styled so many ways.
outfit linked HERE
A comfy little running errands outfit!
outfit linked HERE
Track pants are another fun trend I love! So comfy and cute.
outfit linked HERE
We spent a family day at The Wild Center finding the Thomas Danbo trolls. It was so fun!
outfit linked HERE
This little skirt has been such a fun piece to wear! Neutral and cute with so much.
outfit linked HERE
Another fun little wrap skirt, but this one is denim. I paired it with a tee, cardigan and tall boots (mine are from my college days!)
outfit linked
What I Actually Wore: 12 Casual Outfits
We are starting the slow decline from summer into fall. I’m adding a layer to most of my outfits and we’re starting to see the trees change colors and the nights are beginning to get cooler. I already miss summer because where I live it seemed so short this year. We had a mostly cool June and a pretty cool August as well (the Farmer’s Almanac did predict that and I was hoping it wouldn’t be the case), so we really only had July for good summer weather. But alas, I do love fall and all that comes with it. I am obviously especially excited for fall fashion–denim, boots, scarves, jackets and more! Before we get there though, we have to have some transitional outfits. Check out these 12 summer to fall transitional outfits I’ve worn lately.
I link my looks using affiliate links, This just means if you make a purchase using my links, I earn a commission at no additional cost to you. I appreciate your support!
These shorts are a favorite pair of mine! Stretchy, comfy, soft, and the best color! Loved pairing them with a sweater for this outfit.
outfit linked HERE
I wasn’t kidding when I say I have been wearing this skirt constantly! I love that it’s 100% cotton and a great neutral print.
outfit linked HERE
We had a family campfire and this was so comfy!
outfit linked HERE
These denim shorts have been my most worn this summer! mid-rise and so comfy and cute.
outfit linked HERE
We went fishing and I threw on this comfy little look. Love the color combo!
outfit linked HERE
you’ve seen me wear these pants countless ways at this point–so comfy! I did accidently bleach stain them on the back, but I’ll still wear them!
outfit linked HERE
I love a long sleeve and shorts outfit. This little striped top is a cutie!
outfit linked HERE
I love a pretty little top and pants/skirt outfit. It feels so comfy and so much like ME.
outfit linked HERE
we had a pretty chilly day and I wore this comfy mock neck sweatshirt with shorts.
outfit linked HERE
another easy little outfit that feels super feminine but was also so comfy and easy!
outfit linked HERE
I LOVE these little lace trim satin shorts. They have a stretchy waistband, and I’ve found them so fun to style casually!
outfit linked HERE
We had a day trip to the city and I wore this. Lots of driving so I always want to dress comfy!
outfit linked HERE
12 Transitional Casual Outfits I’ve Worn Lately
It’s time for another outfit round up! We made it through my son’s tonsil and adenoid removal and recovery, and he was such a champ about it all. We are SO happy to be through all of that and on the other side. Most of these outfits are ones I wore during all of that, as we spent quite a bit of time at home. There are many casual and comfy looks with a few dressier ones mixed in.
As usual, I link all of my outfits using affiliate links. This means I make a small commission if you make a purchase–at no additional cost to you. I appreciate your support in helping me keep creating content like this!
Love a linen shorts outfit. So cute and comfy enough to feel like pajamas!
outfit linked HERE
These pull-on pants are from last year, but they brought back a version of them this year, which I am so happy about because I wore them so much last year!
outfit linked HERE
I am not typically an athletic dress kind of girl, but i love this one because it’s comfy and flattering with the cross panel tie waist.
outfit linked HERE
I wore this outfit to the hospital for my son’s tonsillectomy/adeniodectomy and then changed into sweats when we got home. Super comfy easy.
outfit(s) linked HERE
These little cotton denim overalls are so comfy and have been so easy to wear this summer!
outfit linked HERE
This little skort has been a favorite purchase recently! so cute and mom-friendly.
outfit linked HERE
A comfy shades of brown outfit!
outfit linked HERE
This sheer poncho is sooo fun! I can’t wait to wear it more into fall/winter.
outfit linked HERE
Another day, another linen shorts outfit. Also wearing my favorite layer–a denim button up shirt.
outfit linked HERE
These Gap jeans are soooo comfy. I paired them with this black cotton tee and a green crossbody bag.
outfit linked HERE
I’ve worn this skirt often this summer–it’s so fun with its colorful stripes!
outfit linked HERE
These pants again! Love them paired with white and denim so much.
outfit linked HERE
Some Real-Life Outfits I Wore Recently: cold weather friendly
We’re definitely into the cold weather season! That means boots, jeans, layers! All my favorite things. Here are some of my most recent looks.
Everything I’m wearing (or some similar options if the item is older) is linked under each photo! These links are affiliate links, meaning I may earn a small commission. Thank you for being here and supporting me!
This outfit is one of my favorite combos: jeans, a top, a vest and boots. Add a cute bag and you’re good to go!
Outfit linked HERE
I will never stop singing the praises of these jeans—comfy, flattering, and can be dressed up or dressed down!
Outfit linked HERE
Loved the browns and oranges in this outfit!
Outfit linked HERE
I really like a turtleneck look, especially w black turtleneck. I think it’s so classy and cozy and warm.
Outfit linked HERE
Corduroy pants are sooo cozy for cold weather. These ones are a cross between a green and brown color (seaweed, is what is called!).
Outfit linked HERE
Another cozy look—this cashmere cardigan is the best. Has an oversized fit and I love this charcoal color.
Outfit linked HERE
Lace and date night to hand in hand!
Outfit linked HERE
A fun burgundy outfit sandwich!
Outfit linked HERE
A graphic tee and flannel is a classic pairing for me. The pops of orange make it extra fun!
Outfit linked HERE
Love this mustard yellow crewneck (Stay Golden).
Outfit linked HERE
A cozy crenweck is a staple! Paired it with brown leggings and neutral low profile sneakers.
Outfit linked HERE
One of my favorite coats paired with orange accessories!
Outfit linked HERE
This cozy sherpa vest has been a staple this fall.
Outfit linked HERE
Really loved how comfy this outfit turned out. These pants are OOS, but I linked similar.
Outfit linked HERE
You can never go wrong with chocolate brown. Love this crewneck from Walmart and my brown Old Navy barn jacket.
Outfit linked HERE
Just the comfiest! Again with the same crewneck from above and added some comfy pants (same ones from above as well).
Outfit linked HERE
Which outfit is your favorite?