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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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!

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.

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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.

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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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13 Real-Life Outfits for the Winter to Spring Transition

I feel like this outfit round up is full of comfy pieces (helloooo gap factory pants!), pops of color, and just really good basics. Leaning into comfort as we begin to see a bit of spring(ish) weather!

As usual, everything is linked using affiliate links. This means if you purchase something using my links, I earn a small commission. It is no additional cost to you and it helps me to keep creating the content I do. Thank you such for your support—it means the world to me!

Starting off strong with these gap factory barrel pants—prepare to be sick of them because I LOVE how they look and they’re sooo COMFY.

Outfit linked HERE

Loving this sweatshirt still! Such a fun pop of color.

Outfit linked HERE

Sweat sets for home days are a favorite of mine!

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Favorite jeans meet favorite sweater. Add a scarf. Done!

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Green pants and denim tops—a match made in heaven!

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My cowboy boots make me feel so fun!

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Cozy fleece and sweatpants for still cooler days.

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Loved this dress for a baby shower.

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Another favorite pair of jeans—these are so comfy and good!

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A spring walk outfit for when it’s still chilly out.

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This sweater is so cute and colorful—love it for a better than basic look.

Outfit linked HERE

Again with these pants—added a fun colored sweater!

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This coat is a cute pop of color!

Outfit linked HERE

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3 Comfy Summer Items I Ordered From Quince

Over a month ago, I ordered a few spring/summer items from Quince. I have been wearing them on repeat, so I wanted to share a little try-on of them.

I already own two of them in other colors (the grey shorts and green cotton button up) and love them so I knew I would get lots of wear out of different colors of the same items.

If you prefer video content, watch the reel HERE.

You can find these outfits (or similar styles) linked below each photo on my LTK page. I use affiliate links, which means I may earn a small commission if you make a purchase—at no additional cost to you. I truly appreciate your support!

Look 1: Comfy and On-the-Go

I started with a black tank and comfy gray shorts—both super soft and lightweight (I also own these shorts in black). I threw on a belt bag for hands-free practicality (because mom life), and I’m ready! Minimal effort, maximum comfort.

Outfit linked HERE

Look 2: Casual Layers with Denim Shorts

Next up, I styled a basic tank with a pair of denim shorts and layered a breezy button-down shirt over the top. This outfit works great for cooler mornings that warm up fast. This cotton shirt from Quince feels elevated but easy, and you can tie it around your waist later for a relaxed vibe (I also own it on black).

Outfit linked HERE

Look 3: Comfy and Polished

For something a little more polished, I paired a textured white sweater tank (I also own in taupe) with these rust-colored utility shorts from Quince. The earthy tones give this look a slightly dressed-up feel without sacrificing comfort.

Outfit linked HERE

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