Early Fall Outfit Ideas: Casual, Comfy & Cute Outfits for Everyday

September has been quite a busy month with school starting and all the things that go along with that. October is right around the corner and it seems like the cooler weather is here to stay! I’ve been really enjoying dressing more for Fall with all the denim, jackets, and layers. The in between season where I can wear cozy sweaters but also still wear sandals and not really need a jacket yet is one of my favorites for getting dressed–it’s really a fun sweet spot. Here are some of the early Fall looks I’ve been wearing.

As usual, I use affiliate links to link all my outfits. This means if you make a purchase using my links I will earn a small commission–at no additional cost to you. I appreciate your support so much. Thank you!

These khakis are sooo comfy with a stretchy waistband all around them. This dark green color is so pretty and so great for Fall!

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Love these little 100% cotton pants! The black color matches with everything and they come in lengths too.

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These have been one of my favorite pairs of jeans for a few years now. The utility style makes them so fun! Paired them with my brown sherpa vest and a cotton long sleeve tee and sneakers.

outfit linked HERE

This matching set from Old Navy is super cozy and the perfect color for Fall (also comes in other colors, including a really pretty forest green!). I’ve been throwing it on every night to be cozy and comfy.

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These jeans are sooo comfy. They’re a wide leg and come in lots of washes but I love this faded black color.

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This green sweater is 100% cotton and my favorite color! What’s not to like?!

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These have been one of my favorite pair of pants since January. So comfy and I love the green. (see the link below the next photo)

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It’s jeans and cardigan weather! I love this cozy combo, especially with a little scarf accessory.

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Another outfit with this cozy $11 crewneck! The perfect little cropped fit.

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We had a warm-ish day for our pumpkin day this year, so I wore my denim shortalls! So comfy and I love how they look with a long sleeve top.

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I bought this cozy matching set last year and I’ve worn it countless times! The best part is that it’s only $12 a piece and this new crewneck that I bought recently also matches the sweatpants too.

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This little denim wrap skirt is so cute. Love it paired with a sweater, booties, and a scarf.

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Love these wide leg jeans so much! They’re so comfy and cute. I paired them with this fair isle cardigan sweater and my Blundstone boots.

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Wearing these cotton barrel pants again. So comfy and cute with everything!

outfit linked HERE

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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.

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I love a black and denim look. it just always works for me!

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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!

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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.

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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).

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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!

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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.

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A comfy little running errands outfit!

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Track pants are another fun trend I love! So comfy and cute.

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We spent a family day at The Wild Center finding the Thomas Danbo trolls. It was so fun!

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This little skirt has been such a fun piece to wear! Neutral and cute with so much.

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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!)

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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!

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I love a long sleeve and shorts outfit. This little striped top is a cutie!

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I love a pretty little top and pants/skirt outfit. It feels so comfy and so much like ME.

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we had a pretty chilly day and I wore this comfy mock neck sweatshirt with shorts.

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another easy little outfit that feels super feminine but was also so comfy and easy!

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I LOVE these little lace trim satin shorts. They have a stretchy waistband, and I’ve found them so fun to style casually!

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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

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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.

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A comfy shades of brown outfit!

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This sheer poncho is sooo fun! I can’t wait to wear it more into fall/winter.

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Another day, another linen shorts outfit. Also wearing my favorite layer–a denim button up shirt.

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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

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