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.

outfit linked HERE

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

outfit linked HERE

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.

outfit linked HERE

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).

outfit linked HERE

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!

outfit linked HERE

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.

outfit linked HERE

A comfy little running errands outfit!

outfit linked HERE

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

outfit linked HERE

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

outfit linked HERE

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

outfit linked HERE

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!)

outfit linked

Continue Reading

You may also like

Mid-September Outfit Round-Up

I can hardly believe it’s mid-September already! Wow, has this month flown. We’ve been so busy and I can’t even remember what we’ve been busy with, haha.

When September hits, I like to try and get all the wear out of my dresses/skirts before it’s too cold! You’ll find a mix of outfits in this round-up—dressy, casual, comfy, and cute!

If you prefer video content, watch the reel HERE.

All items, or similar options for older pieces, will be linked below each photo. If the exact item isn’t available, I’ll note it in the LTK description. I use affiliate links, which means I earn a small commission if you make a purchase through them—at no additional cost to you. Your support helps me keep creating content like this. Thank you!☺️

I’ve loved wearing this cotton cardigan so much! Since I bought it I think I’ve already worn it 4 times!

Outfit linked HERE.

This denim shirt is SO good! 100% cotton and just the best fit.

Outfit linked HERE.

This little top has been the cutest addition to my wardrobe. I love pairing it with skirts, jeans, pants, really everything! My skirt is from last year so I linked similar.

Outfit linked HERE.

I love a good flannel shirt! This one is from Sawyer Laine Boutique (this color is sold out, but here and here are other prints!). Otherwise I linked a similar one!

Outfit linked HERE.

Black on black with denim is so good! Here I am wearing this denim shirt AGAIN.

Outfit linked HERE

This dress has been a favorite for over a year and honestly just one I want to wear ALL the time! It also own it in red!

Outfit linked HERE.

Just an easy white long sleeve and denim shorts look! Made a little more fun with a cute bag (also, peep the puppy paws ?)

Outfit linked HERE.

I love how this linen outfit turned out! All the best colors and so comfy.

Outfit linked HERE

This maxi is such a good one! I own in two colors and love it! Paired it with this crochet dustercardigan for a cute layered look.

Outfit linked HERE.

Cozy cozy in a matching set and flannel!

Outfit linked HERE.

Hard to see my outfit, but this is what I wore to a night out at the brewery! I’ll link to the collage post so you can see!

Outfit linked HERE.

Continue Reading

You may also like