Not sure what to wear as the cool weather approaches? Read on to see 9 fall outfit essentials you need in your wardrobe in 2020!
Without question, fall is my favorite season. Pumpkin spice latte white girl jokes aside, I’ve lived in the northeast all my life, and there really is nothing on the planet like the weather getting cooler, the leaves turning, and the crisp air that autumn brings.
More than that, it’s the absolute best time of year for fashion. Fall fashion is amazing because it’s so flexible. It’s cool enough to layer but still mild enough out that you can still wear your summer clothes with some tweaks. All you need are a few staples to build out your wardrobe, and it really is that easy to look cute every day of fall with minimal effort.
When I’m dressing for fall, there are a handful of pieces I always keep in mind, and usually integrate into every outfit I wear. Basically, my fall outfit essentials. I wanted to put together a quick guide for y’all of my absolute favorite autumn fashion pieces so you can see how I approach outfit building, and so you can build out your own closet for the season!
In this post, I’ve put together all of my fall wardrobe essentials for 2020. I have links to pieces I know and love, and pieces that are updated for 2020s trends that I’m definitely going to try out this year.
Read on to see what fall outfit essentials you need in your wardrobe this year!
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Tops & Jackets You Need to Wear This Fall
Cute Sweaters
Listen, they don’t call fall “sweater weather” for nothing. The one thing I make sure to stock up on every single fall is a new selection of cute sweaters. There’s just something so effortless and chic about throwing on a statement sweater with some black jeans and ankle booties — you could wear the same outfit formula every day and never get bored.
Some of my favorite places to grab this fall outfit essential are H&M, Aerie, Nordstrom, and boutiques like Vici, Pink Lily, and Red Dress. All of these stores have that great “elevated basics” vibe that I consider my personal style, but still put a unique twist on sweater weather.
Here are some of my picks for the cutest sweaters for fall 2020:
Some callouts on these: Clearly, I love a striped sweater. I love some good colorblocking as well, and I definitely gravitate towards more neutral items.
Two of these pieces, this H&M chunky turtleneck and this cream, tan and green striped sweater, are staples I’ve had a couple years now and I totally love. The chunky turtleneck especially is such a great affordable fall outfit essential that looks amazing tucked into a mini or some skinny jeans, and comes in a ton of colors.
I’m also loving the trend I’m seeing this season of looser, more open knits, like these two options from Nordstrom. I feel like they would be so cute with a lacy bralette peaking through the weave!
Finally, I always love a chenille sweater for fall. It’s just the softest, coziest material, and this spin on the classic fisherman sweater from Aerie looks like it would be such an amazing addition to my fall wardrobe — especially paired with some cute leggings and lace-up boots.
Denim Jacket
One of my favorite pieces to add to my transitional wardrobe is a denim jacket. I love that they’re a little bit edgy, a little bit casual, and seem to go with everything from dresses to jeans (I will rock a Canadian tuxedo, no questions at this time!!
For years, I’d worn a very basic denim jacket I grabbed on a whim at forever 21. This past spring though, I picked up the most amazing cropped denim jacket from Honeybum. I can’t get over the boxy fit, destroyed crop, and perfect amount of oversized this jacket is. It’s definitely one of the best outerwear purchases I’ve made for fall and easily turning into one of my favorite fall outfit essentials.
If cropped and destroyed isn’t your thing, check out the options below to see if you vibe with any of these other cute denim jackets for fall!
Flannel Shirt
There are few things more quintessentially fall than a flannel shirt. I actually haven’t grabbed too many new flannels recently, because I have an arsenal I know and love. But in 2020, a flannel shirt might be one of those fall outfit essentials I need to stock up on.
There are basically two kinds of “flannel” shirts you can get. The first being actual flannel, heavy and warm and stiff. The second being basically a plaid shirt you’re just calling a flannel, but usually made of a lighter material that drapes nicely.
I’m going to share some of both options here, because I think there are so many ways to wear flannels for fall! A heavy flannel is awesome on its own or under a puffy vest. However, I feel like a light, “fake” flannel tied around my waist adds such an awesome, edgier touch to any outfit! Plus — it defines the waist and helps cover the booty if you’re wearing a shorter top or sweater with leggings.
Also in 2020, I’m finding one of the fall trends to be more cropped flannels, which I love the look of! There are some options below from Asos, Urban Outfitters, and more that I think would be super trendy for fall.
Here are some real and “fake” flannels I want in my closet this fall:
Fall Essential Bottoms Your Wardrobe is Missing
Black Leggings
I can’t in good faith recommend any other than these four black leggings. They’re my tried and true, highly acclaimed, perfect black leggings for fall, winter, spring… literally always. They are the ultimate fall outfit essential, and whichever or however many you choose, I know you’ll be satisfied!
My favorite black leggings on a budget are the Aerie Offline 7/8 leggings. I love them for my workouts so much I have them in every color. They’re super affordable, sleek, comfortable and flattering with the best high rise. I absolutely love them.
The next best black leggings are an investment that I personally haven’t even made yet, but I think it’s a universal truth that Lululemon Aligns are the best black leggings out there. They’re not just on the list of fall outfit essentials, but they’re essential year-round, for workouts, travel, and every day. They’re personally on my Christmas list this year!
If you prefer a bit of a thicker black legging for fall, the Zella live in leggings are amazing. I’ve bought two pairs of them over the last three years, and they’re always on sale during the N Sale. They have a little waistband pocket, are long enough for the taller gals, and thick enough to keep you warm in fall.
For something a little basic with a twist, the Spanx faux leather leggings are the way to go. I’ve also invested in these twice in my life (my first pair lasted a good two years of wearing them…literally… every day. like my friends would make fun of me cause they’re all I ever wore. they last!) and they’re worth every penny. Like the Spanx name suggests, they suck you in perfectly, plus the faux leather look is flattering and not cheap like some faux leather can. I totally love these leggings. Best of all, they now come in petite for our shorter girls (me) and tall!
Black Jeans
I love black jeans for fall, and if you’ve been following me for a bit you know I’m pretty particular about my jeans. For the longest time, my absolute favorite black jeans were the Zara Hi-Rise Vintage Skinny Jeans — and don’t get me wrong, I absolutely still love them. They’re one of the best and most affordable fall outfit essentials I like to grab each year.
However, since Abercrombie introduced their Curve Love line, my entire jean world has turned upside down. I’ve said it once and I’ll say it again, I’m built like a Pixar mom: I have a smaller waist and a dump truck behind and for that reason, it’s hard for me to find jeans that fit me well. With Curve Love, I literally don’t have that problem anymore.
Abercrombie has also been exploring a ton of new, trendy jeans for 2020, like straight and wide leg jeans, which I would usually shy away from because of my short legs, but hey, we’re taking risks now. I’m personally crazy about the 90s fit jeans they’re offering, and think I’m going to be adding those to cart next. I also love a simple busted knee black skinny jean, and Abercrombie has a ton of great options for those too.
Here are a few of my favorite black jeans from Abercrombie for this fall:
Plaid Mini Skirt
I feel like the perfect fall date night outfit is a plaid mini skirt, cute sweater, and some over the knee boots. It’s versatile and seasonal and there are so many ways to wear that combo that I can’t get enough of!
Over the years, I’ve collected a solid amount of plaid, checked, and tartan mini skirts. A ton of my favorites are from Abercrombie, but as the mini skirt in fall trend progresses, more and more retailers are sharing their options for plaid mini skirts.
Small note here: while Brandy Melville is definitely a ~leader~ in the plaid mini field, I won’t be linking any of their products here. They’re an insanely size-exclusive brand, and I hate the thought of linking products so many of my readers wouldn’t be able to purchase because they’re not a small/xsmall. Hell, I doubt I would even be able to fit into most of their stuff!
Personally, I tend to go for a more a-line mini skirt with a small notch or slit at the leg. This year though, tennis skirts and the grunge aesthetic are totally in, so a pleated plaid mini skirt would be totally cute for fall too!
That being said, here are some other plaid mini skirts I’m loving for fall 2020.
Must-Have Shoes and Accessories for Fall 2020
Ankle Booties
I went way more in depth about this in my Essential Shoes for 2020 post, but ankle booties are absolutely a fall outfit essential more than anything else.
There are so many different options for ankle booties, but I try to go with some solid neutrals I can wear with anything. I typically like a grey suede, a black leather, and a tan suede ankle boot, but this year I’ve added some white ankle booties and some snake print booties because they’re such a fun trend for 2020.
If you’ve been following my instagram, you know the white and black booties linked below have been my go-tos, but I wanted to share some other options as well.
I tend to go for an ankle boot with a pointed toe because I feel like it makes me look a little taller, and a mid-heel so they’re comfortable enough to wear all day but tall enough to look chic. I’m also still into the sock boot trend from last year — I feel like they’re so cute with a mini skirt or some wide leg, cropped jeans!
Beanies
I love a beanie when the weather gets cooler, but I’ll be honest — I usually just wear an Eagles knit hat instead of buying a ~fashion~ beanie. I want to change that this year! Especially considering a beanie is one of those fall outfit essentials you can bring into winter.
One purchase I’m super excited about is my Flat F*ck beanie from Ohio In My Mind. It’s kind of a weird hockey in joke, but I think it’s hilarious and adorable. OIMM has a ton of extremely cute embroidered beanies with phrases like “wish you were here,” “hometown antihero,” and more. They also have a ton of cute dad hats and sweaters to check out too!
Generally, I like to keep it simple with a neutral colored beanie with a fluffy pom I can wear with anything! Below are a few options I’m loving this year:
Over the Knee Boots
I won’t waste your time or my time. I’ve been over this before. The only Over the knee boots are the Goodnight Macaroon Over the Knee Boots. They are one of my all time fall outfit essentials. They stay up, they’re the perfect heel height, and they look adorable with skirts, dresses, jeans and leggings for fall. I have them in black and grey and I need them in the tan, because they’re that good. I don’t know your life, but I know if you’re wondering what over the knee boots to buy, or which over the knee boots are the best, the answer is these, and nothing else.
I hope this post helped you figure out what fall outfit essentials you need in your wardrobe for 2020!
Now get out there, grab yourself a PSL, and get to a pumpkin patch my friends 🙂
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