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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What I Actually Wore: 12 Casual Outfits

We are starting the slow decline from summer into fall. I’m adding a layer to most of my outfits and we’re starting to see the trees change colors and the nights are beginning to get cooler. I already miss summer because where I live it seemed so short this year. We had a mostly cool June and a pretty cool August as well (the Farmer’s Almanac did predict that and I was hoping it wouldn’t be the case), so we really only had July for good summer weather. But alas, I do love fall and all that comes with it. I am obviously especially excited for fall fashion–denim, boots, scarves, jackets and more! Before we get there though, we have to have some transitional outfits. Check out these 12 summer to fall transitional outfits I’ve worn lately.

I link my looks using affiliate links, This just means if you make a purchase using my links, I earn a commission at no additional cost to you. I appreciate your support!

These shorts are a favorite pair of mine! Stretchy, comfy, soft, and the best color! Loved pairing them with a sweater for this outfit.

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I wasn’t kidding when I say I have been wearing this skirt constantly! I love that it’s 100% cotton and a great neutral print.

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We had a family campfire and this was so comfy!

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These denim shorts have been my most worn this summer! mid-rise and so comfy and cute.

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We went fishing and I threw on this comfy little look. Love the color combo!

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you’ve seen me wear these pants countless ways at this point–so comfy! I did accidently bleach stain them on the back, but I’ll still wear them!

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I love a long sleeve and shorts outfit. This little striped top is a cutie!

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I love a pretty little top and pants/skirt outfit. It feels so comfy and so much like ME.

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we had a pretty chilly day and I wore this comfy mock neck sweatshirt with shorts.

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another easy little outfit that feels super feminine but was also so comfy and easy!

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I LOVE these little lace trim satin shorts. They have a stretchy waistband, and I’ve found them so fun to style casually!

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We had a day trip to the city and I wore this. Lots of driving so I always want to dress comfy!

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12 Transitional Casual Outfits I’ve Worn Lately

It’s time for another outfit round up! We made it through my son’s tonsil and adenoid removal and recovery, and he was such a champ about it all. We are SO happy to be through all of that and on the other side. Most of these outfits are ones I wore during all of that, as we spent quite a bit of time at home. There are many casual and comfy looks with a few dressier ones mixed in.

As usual, I link all of my outfits using affiliate links. This means I make a small commission if you make a purchase–at no additional cost to you. I appreciate your support in helping me keep creating content like this!

Love a linen shorts outfit. So cute and comfy enough to feel like pajamas!

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These pull-on pants are from last year, but they brought back a version of them this year, which I am so happy about because I wore them so much last year!

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I am not typically an athletic dress kind of girl, but i love this one because it’s comfy and flattering with the cross panel tie waist.

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I wore this outfit to the hospital for my son’s tonsillectomy/adeniodectomy and then changed into sweats when we got home. Super comfy easy.

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These little cotton denim overalls are so comfy and have been so easy to wear this summer!

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This little skort has been a favorite purchase recently! so cute and mom-friendly.

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A comfy shades of brown outfit!

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This sheer poncho is sooo fun! I can’t wait to wear it more into fall/winter.

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Another day, another linen shorts outfit. Also wearing my favorite layer–a denim button up shirt.

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These Gap jeans are soooo comfy. I paired them with this black cotton tee and a green crossbody bag.

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I’ve worn this skirt often this summer–it’s so fun with its colorful stripes!

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These pants again! Love them paired with white and denim so much.

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Casual and Put Together Summer Outfits I Actually Wore: Outfit Ideas for Petites

Something I’ve realized about myself since taking photos of my outfits and homing in on my personal style is that I am a HUGE fan of a neutral base and a pop of color. It usually makes for a great outfit that makes me feel confident and makes me feel like me and this is exactly how I’m trying to feel when getting dressed. Not every outfit follows this color combo, but I do enjoy when it does. Here is my round up of my latest outfits.

As usual, I am linking all of my outfits using affiliate links. This just means if you make a purchase using my links, I earn a small commission, at no additional cost to you. I appreciate your support so much!

This black gauze button up is one I reach for CONSTANTLY. I bought it last year and it works so well as a little lightweight layer.

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I recently bought this little skort (always love a skirt with built-in shorts!) and it’s sooooo cute. Love the neutral print, the comfort and that it comes in size xs!

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I am officially a believer that a neutral (black or white or both!) gauze cotton maxi skirt is a wardrobe workhorse. It’s so comfy, breathable, and so fun to style.

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I have been loving this little 100% cotton faux wrap skirt. It’s so comfy and adorable and is going to be so fun to continue to wear into fall.

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We have had some cooler days, so I pulled out my barrel jeans. They felt just as good as last year and I can’t wait to wear them more as we head into fall.

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We went to see Tim Mcgraw for our 11 year anniversary and this is what I wore. It was easy, comfy and I felt great in it!

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I bought these little brown satin/lace shorts awhile back and was so excited to get a chance to wear them casually. They’re super comfy with a stretchy waistband and so cute.

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I wore this dress in the spring for one of my family Easter events, and it’s also a great one in the summer too! So pretty and feminine.

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These red pants have been SO fun to wear. I love the gauze cotton and how fun they are. They are sold out, but I found some similar ones.

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Don’t mind my wet hair in this picture– I was air drying my hair and we were headed out. An all black outfit is always a favorite!

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My mom and I and my boys and nieces all went blueberry picking and I wore an easy denim shorts and old navy tank outfit.

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I have been loving boxer shorts so much! They’re so comfy and easy to style. This red striped pair has gotten SO much wear this spring/summer.

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My cousin got married and I wore this cute little green floral dress. It was comfy and I felt great in it!

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A little pool day look with my favorite crochet coverup and a bikini!

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This was an easy little Sunday afternoon outfit. Love these ripstop shorts!

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