Cool Girl Fall Series:  Denim Jacket & Black Distressed Jeans

So there was hot girl summer, then Christian girl autumn, but what about cool girl fall? I’m talking the girl who looks effortlessly cool, like she didn’t try, yet put together wearing an envious neutral look.

Enter, cool girl fall. This September, I’ll share a look every Monday that embodies “the cool girl” – which is totally achievable and you probably have most items already in your closet!

The essence of the cool girl is minimal and neutral. Key staple pieces end up standing out. This first look of the series is one of my “go to” outfits for keeping a neutral color palette, and giving that I didn’t try too hard but still look put together outfits.



This denim jacket / black jeans look is the outfit I wear when either when I’m sure about the vibes, or if I’m meeting new people but in a casual setting like going to meet for lunch. Insert me in a picture actually wearing the outfit in real life to meet Olivia from OliviaSheaStyle for the first time and wanted to wear a “cool” outfit.

Oversized Jean Jacket

Keyword  – oversized. The cool girl layers, so there needs to be room to add something underneath. She might also add another feature to the jean jacket – maybe it’s distressed, has patches, embroidery, built in hood, or like here, has pearls and beads. Sherpa lined fleece is also very in for fall and winter, but doesn’t translate to spring / summer, so I wouldn’t go that direction if you want something for all seasons. Even though it’s on trend right now.


Distressed Black Jeans

Keyword again – distressed. To me, wearing plain black jeans just looks like leggings, so I make sure to differentiate with some holes. They don’t need to be majorly distressed (I distressed mine myself and got a little too happy with the razor blade) but a hole or 2 in the knee is a good touch!

I’m wearing the AG Farrah High Rise Skinny Jeans (highly recommend, very stretchy but I distressed myself), but another one of my favorite stretchy jeans are my Rag&Bone jeans. I found a Rag&Bone pair that’s an extra 30% right now making them $111 instead of the normal $225 price!


White Cotton Sweater

Ahhhhh, there is nothing better than a white cotton crewneck sweater. I wear this thing with everyyyyything, every season. And so does the cool girl. For this fall transition season, its easy to add a cardigan or jean jacket over it needed for layers. Or, if it’s still too hot outside, you can pair this with jean shorts or a maxi skirt instead. Honestly, endless combinations with this. Mine is JBrand from a few years ago, but linking similar high quality ones below. I really love the Jcrew Factory Rollneck, I have it in olive!


[White] Sneakers

Now that I’m halfway into this post, I’ll admit I took these pictures in March of 2018. LOL. It’s now September. My feed was starting to look more summery so I LITERALLY I HAVE BEEN SAVING THIS IDEA FOR 6 MONTHS. Anyway, at the time I hadn’t 100% mapped out how I would form the blog post, but I know if I redid pics now with my full “Cool Girl Fall” vibes, I would have gone with booties! But platform sneakers work too! Basically, something that gives you a little height but still super comfortable. I Especially in white! White shoes are the epitome of cool girl because she’s thinking, “yeah, I know white gets dirty, but I don’t care. I care more about trends than practicality. And there’s a little invention called bleach.”  Also – inserting Dad Sneak trend here works.




A cool girl always has her shades. At the time of picture, I didn’t have my Ray Ban Rounds or Ray Ban Hexagon’s, (also check out my Ray Ban Guide here) but those are the ultimate cool girl shades. If you want to be more fun, an oversized pair works or add a pop of color with mirrored sunglasses!


And that’s it! That’s all you need for a cool girl outfit. You probably already have black jeans, some type of white top (could even be a tee) and a jean jacket! If you don’t you can shop all the links above!




PS – here’s one more look at the back of my jean jacket from a different time I wore it!

Hi, I'm Anna!

Welcome to the corner of the internet where you’ll find boho & bright style, travel adventures, and life in my latest “hometown” – Nashville, Tennessee. My love and I recently bought a house – and we’re taking on the renovations ourselves! You’ll be seeing more home content here – from DIY tutorials to home decor inspiration. We have a LOT of ideas for this house, implementing slowly one room at a time!

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