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Classic Fall Fashion for Girlbosses

Classic Fall Fashion for Girlbosses

Photo by  Jeff Hardi

Photo by Jeff Hardi

Girlbosses, it’s finally time to pull out those sweaters! These fall classics will have you looking cute from the pumpkin patch to the office. As entrepreneurs, we want to look stylish but hardly have time to do our makeup (much less put together a whole outfit!). These pieces are super easy to mix and match, so they’ll give you an effortless fall style without taking time out of your morning. And they come at great prices because yeah, we’re all ballin’ on a budget.

The key for fall -whether you live in Florida or Maine- is layers! Where I live, it’s 45 degrees in the morning and 70 in the afternoon. I always make sure to wear a blouse that can stand alone and throw a comfy cardigan or sweater over it for the mornings. I also usually leave the house with thick socks (any Smartwool lovers out there?) and throw an extra pair of short ones in my bag in case I get hot. Finally, I throw on a patterned scarf just for fun. The important part is to wear pieces that can be layered when it gets cold and stand alone when we’re lucky enough to get some heat. Check out these items I love to layer and play with when my favorite season comes around!

The Classics

Pair these with any piece and you’re set to go!


The White Button Down

I’ve been loving the white button-down look with ankle boots and a long cardigan. The important thing here is to find one that is light enough to layer but won’t be see-through. I’ve been loving this style from Everlane (so soft!) or the more classic look at Banana Republic.

P.S. Check out Caroline Joy’s Five Ways to Wear a Button Down (Pictured)


The Carryall Tote

Are these bags perfect for any fall outfit? Yes. Are they spacious for packing extra layers? Always. Can they store the excessive amount of mini pumpkins, cider donuts, and halloween candy you might be collecting this season? Absolutely.

-DSW Top Zip Tote

-Madewell Transport Tote

Photo by Leather Cove


The Overall Dress

Look chic and stay comfy in these playful pieces. These jumpers come in so many styles and materials and are amazing for layering. Perfect for throwing on over a turtleneck and tights, these pieces will make you look cool while the temperature drops.

-Roolee Cathan Button Jumper (Pictured)

-Anthropologie Hattie Dress

The Ankle Boot

You simply can’t go wrong with these! Throw them on with literally anything and you’re all set. Be sure to take inventory of your pants before you buy a pair- it’s important to find boots with a length than works with most of your pants. I tend to wear a lot of skinny jeans, so I go for medium length boots, but someone with more cropped jeans might need a half-calf style.

-Nordstrom MIA Boot (Pictured)

-Nordstrom Dolce Vida

-Sam Edelman Packer Booties

The Chunky Sweater

Chunky sweaters make creating a cute outfit easy peasy. Check out different styles before you invest- I personally like drop shoulder sweaters (arm seam is cut lower than the shoulder, as pictured) because of my athletic frame. Whether its a crewneck, v-neck, or cowl neck, find a style you love and invest in one you can wear from October to March!

-ASOS Design Cable Sweater

-Everlane Soft Cotton Crew

-Weststylish Turtleneck Sweater

Photo by @night.changes

My Picks

Here’s what I’ve been digging this season!


Plaid Blazers

My layering essential for this fall! Somehow I feel both intelligent and chic in this piece. Be sure to opt for a slimming cut to avoid looking like you borrowed this from your grandpa’s closet!

-Mango Checked Unstructured Jacket

-Loft Double Breasted Blazer

-Everlane Oversized Blazer in Glen Plaid

Photo via Pinterest


Black Mom Jeans

These are my favorite pants for any weekend adventure. Pair these with a cute belt, a tucked in shirt, and a long cardigan for a casual look. Look for a pair with structure and comfort, like my faves from Everlane.

P.S. Don’t shy away from a pair that might need to be broken in, that just means they’re made of high quality denim!

-Everlane Cheeky Bootcut Jean

-ASOS Stradivarius Mom Jean

-ASOS Monki Kimono High Wasted Jean

Photo by Levi’s

Chelsea Boots

I think I’ve worn my black Blundstone boots every cold weather season since I bought them. Extremely comfortable and durable in any weather, Chelsea boots like these will pair with almost every outfit. Blundstone also makes a dress pair with a chiseled toe perfect for work!

-Blundstone High Top Boots

-Vagabond Shoemakers Kenova Hiker Boot

-Public Desire Heeled Boots

Photo by Style Bee


Button Up Cardigans

Did I mention I like layering? Wrap up and stay cozy in a soft cardigan and hook one button for a cute and casual look.

-Lou & Grey Pocket Boyfriend Cardigan

-Everlane Cotton Cardigan

-H & M Rib Knit Cardigan

Photo by LilCloth

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Embroidered Sneaks

If I’m not in my Blundstones you’ll most likely find me in comfy white sneakers. I’ve been loving the embroidered style for a way to spice up the classic look and add an extra pop of color to my look (my wardrobe literally consists of black, green, and white so this is huge!).

-Soludos Rainbow Wave Sneaker (Pictured)

-Keds Embroidered Rosalie Sneaker

-Saludos Peace Out Sun Sneaker

Want more? Check out The Work-Life Style of… Kristen!


INSTAGRAM: @rutzcrackerz

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