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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15 Comfy Fall Outfits I’ve Worn Lately in Real Life

Fall weather has me dressing in warm colors, fun layers, and comfy sweaters and sweatshirts. I’ve been loving all of the fall outfits and staying cozy and warm!

Here are 15 outfits I’ve worn out and about in real life lately.

As usual, everything is linked below each photo. I use affiliate links—which means I make a small commission if you purchase using my links. I appreciate your support in helping me continuing to make content.

These brown leggings are so good (I really love the no front seam!) and they were really cute with my grey hoodie and Bearpaw slipper clogs.

Outfit linked HERE

This is one of my FAVORITE outfits lately. I loved the feminine lace skirt mixed with the green graphic tee.

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I bought my Columbia fleece vest last year and was super happy to pull it out again as a layer when it got cooler. It’s always cute with a crewneck sweatshirt!

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Burnt orange is one of my favorite colors and this babydoll top is so perfect for fall.

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I was pleasantly surprised by how much I love these barrel jeans. Loose and comfy and cute!

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A maxi skirt and sweater is a great fall outfit! Add some boots and a suede bag and you have the perfect fall look.

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My 100% cotton button ups are some of my favorite layering pieces and I’m bringing them into fall with jeans!

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This lace trim sweatshirt is so adorable. The lace adds fun detail and I paired it with comfy jeans!

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This puffer pullover is another piece from last year and it’s a great light layer!

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These brown barrel pants have been such a favorite! They’re cotton and twill and so comfy!

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This was a hiking outfit for a day of chasing waterfalls. So fun!

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My denim dress is sold out at this point, but it’s such a staple! I linked similar ones. It’s so cute with a cardigan layer and cute clogs.

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My favorite Walmart crewneck is back in cream and some new colors (I picked up chocolate brown!)

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This sherpa is so cozy and the perfect cozy layer! another piece from last year that I love.

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Always love to pair my cowboy boots with denim shorts when it’s a warmer fall day.

Outfit linked HERE

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