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7 Classic Fall Wardrobe Essentials Every Woman Owns

There’s certain classic pieces we all have or need in our closets when it gets colder. I’m getting excited with each day because that means I’m closer to wearing my jackets and whatnot and really leaning into my tomboyish side; I’ve already started perusing Pinterest for outfit ideas. If you’re anything like me, you have a fall/winter casual #OOTD formula you go for: coat, pants, inner layers, and boots.

Start shopping right now for these classic fall wardrobe essentials. I’m in the mood for shopping the vintage route for some of these essentials or splurging a bit on them because I know I’ll have them for years to come.


Whether faux or real, leather is an essential everyone can wear when it starts feeling a little cool outside or during warmer months(depending on the item). Right now, I’m on the hunt for a short leather skirt I can dress up or down and wear with everything from basic tees to sweaters.


I remember wearing so many cardigans and sweaters in my undergrad days. This cozy piece is great for layering over (or under) dresses, skirts, and leggings. Wear it as a shirt with a blazer too. I plan on wearing all of mine either with shorts and ankle boots for brunch or jeans and t-shirt for a casual #OOTD.


Sweatshirts are some of the most comfy thing to wear when it’s cold outside. Last year, I bought a few new ones last year so I have a good rotation to wear with jeans or over dresses if I felt like it. I’ll be wearing mine under my jackets and trench coats all season long as shirts. I tried tucking them in to jeans recently and I’m kinda feeling it. Usually, the items can look bulky but tucking helps define my waist and brings some structure.


I started loving trenchcoats a few years ago when I purchased my first thrifted one. I had it for years before wearing it for the first time in D.C. in 2018. The thing I love about trench coats is they’re a super duper classic fall wardrobe essentials that I know I’ll have forever. Fortunately for us now, there’s way more opportunity and places to purchase pre-owned/vintage ones. I had a dream one night last year that I had a Christian Dior trench and after scouring eBay and Poshmark, I found the exact one I wanted within the week. Both trenches are neutral colors so they pretty much go with anything and everything in my closet. My favorite way to wear them is with a sweats and boots (or sneakers) for a comfy, cool look with sunnies and a crossbody bag.

Denim Jacket

A denim jacket is an item that works year-round but mainly when it gets cold. Although it’s not as humid as it was last month, temps in Florida are still reaching 90 degrees so wearing one during the day doesn’t really work. It’s easy to wear with a slip dress and sneakers for day or go the Canadian tuxedo route with a pair of jeans in a contrasting wash.


It’s not often I wear sneakers but during fall and winter, I’m wearing one of several pairs of Converse I have or whatever other sneaker I feel for the day. This time of year is when I really get the most wear out of my sneakers outside of work. Now, I’m not a sneaker head at all; majority of the sneakers in my closet are from my undergrad days. The one thing I’m glad about is that they are pretty unique so there isn’t a chance I’ll find someone else wearing them.


A good boot will get you through the entire season. Combat boots to over-the-thigh boots go with pretty much our entire wardrobes from everything short to long to oversize. I bought a pair of Dries Van Noten ankle boots I’d been searching for for at least a year because I saw Tracee Ellis Ross with a similar pair. I’m trying to wear them with any dress or straight leg jean I can find.


What classic fall wardrobe essentials are you in the stores shopping for at the moment?