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.

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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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Outfits I’ve Loved Wearing So Far This Winter

I feel like I’ve found such a groove in getting dressed, in such a good way. I am loving the casual but put together feel that most of these outfits give off and I’m especially loving how they make me FEEL. There is nothing better than an outfit that makes you feel amazing and is still so comfy!

Here are 16 outfits I’ve worn over the last couple of months!

Everything I’m wearing is linked under each photo, and I’ve added similar finds for anything that’s older. These are affiliate links, so I may earn a small commission—thank you endlessly for supporting me, it truly means so much to me🧡

Loving this heavy green sweatshirt! The big buttons make it fun too!

Outfit linked HERE

I’ve been enjoying these comfy pants —I’m wearing the petite length and they come in regular length too!

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These pants are my favorite new item of 2025! I’ve loveddd wearing them! Perfect for dressing up or down!

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I think this sweater sold out (🥲) but maybe it’ll restock?! It’s such a cute one and I’ve received so many compliments on it!

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Corduroy and pop of red? Yes please!

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I just love puffer vest season! And I really love a fun colorful scarf too!

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Can you tell this sherpa has been on repeat (based on my last post too?😝)

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Jumped on the little triangle scarf trend (reminds me of the scarves I used to wear in college!) and I think it’s too cute.

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Been wearing this sweat set TO DEATH. So cozy!

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A crewneck is my favorite “I don’t wanna think about what to wear” outfit!

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This sweater is so fun with all the colorful Pom Pom pieces in it!

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Green on green forever— another puffer vest look!

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These barrel pants have been such a favorite for years. They’re so comfy!

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A printed sweater makes an easy cute outfit.

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Another pair of jeans I’ve been loving—a super comfy straight leg pair.

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Comfy cozy outfit!

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Six Pairs of Shoes I Like to Wear with Barrel Jeans

Barrel jeans have become one of my favorite denim silhouettes. they’re relaxed through the leg, taper slightly at the ankle, and look effortless and put-together at the same time. But the question I get most often is: “what shoes can I wear with them?”*

Because of their shape, barrel jeans can be a little tricky to style. The solution is pairing the curved, voluminous leg with shoes that ground the outfit and highlight your ankle or add just enough height.

So today I’m breaking down six pairs of shoes that I think complement barrel jeans perfectly!

If you prefer video content watch the reel HERE.

As usual, you can find everything I’m wearing (or similar pieces) linked under each photo! These are affiliate links, so I may earn a small commission if you purchase anything using them—thank you for supporting me and my content🤎

1. Mary Jane flats—I think a pair of Mary-Jane flats can go well with so many jeans! With barrel jeans, they bring a touch of femininity to the more masculine silhouette. 

Outfit linked HERE

2. Low profile sneakers— the low profile sneaker helps to balance out the wider fit of the barrel jeans by showing your ankle a bit.

Outfit linked HERE

3. Clogs (heeled or flat)—I’m a big fan of clogs in all styles! They go with so many types of pants and dresses and skirts! They go well with barrel jeans because they help balance the volume.

Outfit linked HERE

4. Heeled boots— I love a heeled boot as a dressier option. The heel obviously adds some height and visually lengthens the leg line. 

Outfit linked HERE

5. Slipper clogs—comfy and cute, I love these with barrel jeans! I feel like the bulkier shoe looks cute  with the volume of the barrel jeans.

Outfit linked HERE

6. Chelsea boots—I didn’t get a chance to add them in my video, but I also like to wear my Chelsea boots (Blundstones included!) with them. I know this may be a controversial opinion—because there is a lot of chatter around it making the legs too bulky—but I think the cropped fit of the jean and slim shaft of the boot look great together and it’s super fun functional! 

Outfit linked HERE

When it comes down to it, it’s all personal preference! There are NO hard and fast rules and you should really wear what you want to wear and what feels good.

What’s your favorite kind of shoes to wear with barrel jeans?

*this post is part of a series on what shoes to wear with what jeans, I’m calling it “The Jean & Shoe Guide”. I started with wide legs and you can find that post HERE.

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17 Comfy and Cute Fall Outfits I’ve Worn Recently

We’ve had some great fall weather lately! It got a bit warmer for a little bit (as you can see below with a few shorts outfits), but now it’s back to the cooler for fall-like temps.

We have really been enjoying all the fall activities—hiking, oktoberfests, fall walks, campfires, and more. Here are some of the outfits I wore while doing these things.

You can find everything I’m wearing (or similar pieces) linked under each photo! These are affiliate links, so I may earn a small commission if you purchase through them—thank you for supporting my content🤎

We hiked a mountain with my sisters and their families and and got to see the beautiful fall foliage!

Outfit linked HERE

These brown pants have been perfect for fall weather!

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A black cardigan is such a classic! Love it paired with easy relaxed barrel jeans.

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I’ve been loving wearing my dark brown barn jacket! the black corduroy collar makes it so cute!

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Overalls and a tank are a perfect “warm fall day” outfit.

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My fleece vest is the perfect layer over a cozy crewneck sweatshirt

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I’ve been loving a lace skirt with a casual top. The satin printed scarf and cowboy boots really made this outfit feel like me and so cute.

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A skort and crewneck sweatshirt with sneakers was perfect for a fall walk.

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Just the simplest outfit—a black tee and jeans—made cuter by a scarf tied around my waist.

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One of my favorite dresses paired with a denim jacket and neck scarf and clogs!

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I love chocolate brown and this crewneck is super cozy.

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I recently shared a reel with my quilted vest—it’s been in my closet for about 3 years now. It’s so cute with so many different things. Here I paired it with a denim mini skirt, heeled clogs, and a white long sleeve.

Outfit linked HERE

Another warm fall day—I paired my cotton boxer shorts with a graphic tee and denim shirt.

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Loving that this brown sherpa vest is such a cozy and cute layering piece. It’s fun over sweaters, sweatshirts and more.

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We want to a fall festival and it was quite warm out—this outfit was perfect!

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Another brown pants outfit! Love these pants paired with a tee and flannel shirt.

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A Henley sweater and barrel jeans with my low-profile sneakers felt great!

Outfit linked HERE

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