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

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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!

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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.

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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.

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

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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.

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Again with these pants—added a fun colored sweater!

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This coat is a cute pop of color!

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