Let’s talk 2020 Fall & Winter Fashion Trends! First of all, I think you’ll agree with me that 2020 is the strangest year we’ve ever seen. The COVID-19 pandemic has changed things in business, entertainment, travel, dining, home life, and so much more. Add fashion to that list!
Gone (probably forever) are the days so cutely memorialized in the 1988 movie, “Working Girl,” where Melanie Griffith’s character rushes into her office scrambling to grab a ringing phone while yanking off her Reeboks and tube socks to slide on a pair of heels. Of course, even before the pandemic, you could find sneakers in some boardrooms, but what I don’t think we’ll see from now on is such a definitive distinction between work clothes and home clothes.
Oh, and, can we please talk about the evolution of those “home clothes?” Even if you’re working from home, you’re looking for clothing that will take you from workouts to household chores to Zoom meetings to masked-up errands. (And let’s not even talk about some of our poor millennial daughters who are also trying to wrangle their kids and maybe even home school! )
As our carefully socially distanced calendars begin to fill up again, the round-the-clock loungewear we were all wearing at the beginning of the pandemic may no longer fit the bill. So what will take it’s place? What we’re seeing is some new kind of hybrid fashion.
Although women may be ready to get “dressed” again, they aren’t necessarily ready to sacrifice the ease that came with dressing down. Oh, and don’t forget the lovely “Quarantine 15” that so many people now have to camouflage.
The 2020 fall and winter fashion scene is ripe with a few specific trends. Today I’m sharing them with you, along with my “Pro Tips” for making these trends work when you’re over fifty! Look for the bolded text for the must-know info! (Suzy made a rhyme! )
As always, click on any pink text link or image (including the collage above) for more information or to shop.
Here’s what you need to know as you go through my comprehensive 2020 fall & winter fashion trends post:
This post is best viewed on a laptop, iPad, or other tablet. On mobile, the images may be too small to see clearly.
For size reference, I am 5’5″ and wear an XS or XXS. (Read that: flat-chested! ) Also, remember that the models you see in the photos are often really tall, making things look shorter than they are!
I worked hard to find well-priced and affordable examples of each trend.
I focused on in-stock, highly rated items.
Many of the items featured in my example images come in multiple colors and patterns. If you like a style, be sure to click on it to see the other options!
Many of the items featured also come in petite and plus sizes.
There are some great sales this weekend! If you like something you see, click through to see if it might be on sale.
Thanks for shopping with my links! When you click through on either text or image links, I earn a small commission if you make a purchase. Your support enables me to continue to do this job that I love so much!
Hot Colors & Patterns to Watch For
Hot 2020 Fall & Winter Colors
Light Coral & Dark Coral
Hot 2020 Fall & Winter Pattern: Camo (But Reimagined!)
Cinch-Waist Floral Camo-Print Rain Jacket | Long Sleeve Crew Neck Tee | Similar Khaki Jeans | Similar Khaki Sneakers
Animal prints are still out there, and you’ll still see last year’s obsession with snakeprint, but this year, look for camo reimagined! Watch for camo’s more feminine makeover, incorporating a subtle floral into the design, or just using camo in an unexpected spot.
2020 Fall & Winter Fashion Trends: Zoom-Worthy Tops
Animal Print Tie-Neck Blouse (similar) | Black Stretch Ankle Pants | Black Belt | Black Block Heel Sandals
Look for tops with statement making details above the waistline. High necks plus a touch of frill gives your run-of-the-mill blouse a chic update. Not into frills? Embrace the stand-collar neckline instead.
***Suzy’s Pro Tip For Women Over Fifty: Tie-neck tops are still everywhere. If you love this style, be sure to wear them with the bow untied for a more casual, less prim and proper look.
Georgette Half Sleeve Ruffle Neck Blouse | Leopard Print Calf Hair Belt | Block-Heeled Sandals | Tory Burch Micro Bag | Initial Necklace | CZ Pave Hoop Earrings
Ruffled necklines are everywhere! (Thanks, Zoom!) Also look for shirred neck tops, which fit closer to the skin like a turtleneck.
***Suzy’s Pro Tip For Women Over Fifty: If you’re not crazy about your neck or jawline, take them into consideration when choosing your top! A soft, higher ruffle (THIS top is a J.Crew best-seller!) that doesn’t hug the neck skin can hide neck wrinkles, while a lower, tiny ruffle can distract the eye from a jawline that isn’t as tight as you’d like.
Call it the evolution of the statement sleeve! Although we’ll still see balloon sleeves and other statement making looks, the focus this year is on shoulders. (Thanks, Zoom!) Especially noteworthy: sheer detailing on sleeves. (Soooo pretty!)
***Suzy’s Pro Tip For Women Over Fifty: While the feminine puffy sleeve trend is beautiful at any age, know that the older you are, the smaller the puff, the better!
2020 Fall & Winter Fashion Trends: Faux Leather
This trend is awesome! Look for easy care (machine washable) faux leather styles. My new fave is this puffy sleeve top! Also, if you don’t have a faux leather moto/biker jacket, you need one! I own THIS one from Chico’s.
2020 Fall & Winter Fashion Trends: Elastic, Pull-On Waistbands
Pull-On Jeans (These are reversible and come in a variety of patterns/colors) | Twist Front Tee | Coordinating Twill Denim Jacket | Blush Suede Perforated Slip-on Sneakers (Similar) |Pearl Initial Necklace | Pearl Cluster Earrings
From faux leather joggers to animal print jeans, look for pull-on styles that are easy-to-wear!
2020 Fall & Winter Fashion Trends: Puffy Pieces
It’s not your mama’s bedspread, that’s for sure! These quilted styles feature elevated textures and fabrics that are perfect for cold-weather wear.
***Suzy’s Pro Tip For Women Over Fifty: Watch out for this trend! You don’t want to add bulk in the wrong places! Maybe opt for a slimmer-profile vest or jacket instead. (J.Crew did this so well this year, opting for a slimmer, quilted take on the trend. Click HERE to see what I mean!)
Look for cozy sweatshirts with surprising, fun prints, ruffle necks, button collars, or pearl detailing.
2020 Fall & Winter Fashion Trends: Sweater & Sweatshirt Dresses
Go for an oversized sweater dress for a cozy, comfortable look. Pair with regular boots or over-the-knee boots, booties, regular sneakers or wedge sneakers. (I own and love THESE wedge sneakers!) Think about adding a vest or scarf for fun! Also, in maybe the greatest invention of all time, look for the sweatshirt dress! Wear it the same way as the sweater dress!
2020 Fall & Winter Fashion Trends: Pearl Party
Pearl detailing is everywhere this year! Yes to pearl accessories, for sure! (Watch for my next post on the 2020 Fall & Winter Shoe & Accessory Trends.) But also yes to pearl detailing on tops, bottoms, and even dusters!
2020 Fall & Winter Fashion Trends: Elevated Loungewear
Cap Sleeve Tee | Slim Cropped Pants | Calf-Hair Leopard Print Belt | Black Pumps
Did you see my recent post with Lilysilk? They’re my go-to spot to shop for affordable silk! Want to upgrade your lougewear? Silk is an updated way to do it! We’re seeing more and more of it out there. My post explains what to look for in terms of quality, and how to care for it, etc.
This is not a green screen! This really is the view at our condo in Sanibel Island! Also, may I just say that I got SUPER excited when it looked like I had cleavage in this picture!!! (Spoiler alert: I. DO. NOT.)
Palm Print Cropped Leggings | Long-Line Padded Sports Bra (Amazon Best-Seller) | Sneakers | Sunglasses | Lipstick
Print and patterned leggings are such a fun way to show your personality without spending a lot! Pull out a color in your leggings that you feel good in and put an on-trend twist front or tie-waist tee on top!
***Suzy’s Pro Tip For Women Over Fifty: Look for a top that comes down far enough for modesty. Think about something like this long, tunic length elevated sweatshirt that I own to make the patterned legging trend your own!
Let’s be real. Joggers are really just slightly more fitted sweats than the ones we wore around the dorm or sorority house in college! That said, they’re on-point right now, and women over fifty can wear them.
***Suzy’s Pro Tip For Women Over Fifty: Be sure to pair a loose fitting jogger on the bottom (THIS pair is so cute!) with a fitted top so you don’t add girth! If a fitted top makes you self-conscious, consider adding a faux leather moto jacket or other waist-length (now called “cropped”) cardigan on top.
Twist-Front & Waist-Tie
Twist-Front Top (Amazon Best-Seller; lots of color options) | Bronze Faux Leather Leggings (on sale)| Filigree Earrings
A twist-front is a great way to add interest and texture to an otherwise plain top!
Twist Front Three Quarter Sleeve Knit Top (From my fave Amazon brand! Also in navy, black, and hunter green)| Reversible Twill Pull-On Jean (These are the ones from the pull-on jeans section above – just reversed!)| Similar Pink Sneakers | Kendra Scott Drusy Earrings (Amazon lookalike Drusy earrings HERE) | Yeti Stainless Tumbler
Waist-Tie Dress (Comes in multiple colors) | Block Heel Sandals | Rattan Earrings
***Suzy’s Pro Tip For Women Over Fifty: The twist-front or waist-tie provide “strategic” ruching, which makes this a super-flattering style for women over fifty.
2020 Fall & Winter Fashion Trends: Oversized & Boxy
If you have a larger bust, you’ll love these styles!
For a pulled-together look, throw on a double-breasted style before a Zoom meeting or when running errands.
***Suzy’s Pro Tip For Women Over Fifty: Remember that, when worn unbuttoned, the double-breasted style can visually add width due to the way it hangs. I’m not a fan unless it’s done with a nipped in waist, like THIS one from Express!
Oversized, Sweater Blazers
In an effort to look pulled together, yet remain comfy, look for oversized, sweater blazers. THIS line at J.Crew has a bunch of great colors. (Can I hear you say “Best of Both Worlds?” )
Now, don’t freak out! The word “cropped” now refers to a flattering waist-skimming length! Look for a couple of cropped cardis to add to your wardrobe (especially if you’re cold-natured like I am!) They can be boxy or slightly more fitted. I think the best selection and quality for the price is at Boden.
***Suzy’s Pro Tip For Women Over Fifty: This waist-defining shape is often more flattering than a hip-length or longer. It creates a waistline!
2020 Fall & Winter Fashion Trends: Continue to Wear
Leopard Ruffle Collar Knit Top | Similar Black Skinny Jeans (Without raw hem.) | Chain Link Mules
Animal-Print Skort | Cotton Bateau-Neck Tee | Black Allbirds Sneakers (Amazon Lookalikes HERE)| Rattan & Straw Fan Clip-On Earrings
Tie-Dye Loungewear Set (Other colors/patterns available) | Pink Bandana
Tie-Dye – Check out the entire post I did on how to wear the tie-dye trend if you’re over 50.
Fringe and Western
2020 Fall & Winter Fashion Trends: What I’m Buying & What I’m Skipping
I think your decisions about what to buy and what to skip is pretty personal! Consider things like your lifestyle, plans for the future, body type, and priorities.
Here’s What I’m Buying:
As you can see from the photos in this post, I’ve already started buying! Hey, it’s part of my job!
THIS sweater dress. (Cute with or without a belt!)
THIS faux leather puffy sleeve top.
THIS cozy animal print tunic. (Cozy over leggings!)
THIS faux leather moto. (I consider this a must-have piece!)
THIS perfect-for-transition short-sleeve camo puffy sleeve top.
THIS cute waist-tie waffle knit top.
Here’s What I’m Skipping:
I’m mostly down for the 2020 fall & winter fashion trends, but I’ll draw the line when they just swim on me!
Oversized Cardigan Sweaters
Boxy Crop Cardigans
Wide Leg Pants – I just don’t think they provide a flattering silhouette for anyone! That’s why they’re not even included in this post!
Remember that many of the 2020 fall & winter fashion trends I featured in this post are on sale this weekend! I hope you clicked through on anything you liked, just in case! If not, take another look at them below!
I don’t know about you, but it always takes me a little while to get used to the new trends! I think it helps to see multiple examples, don’t you? I’ve pulled together lots of affordable examples of the trends in a boutique below this post. Click on any item for more information or to shop.
What 2020 fall & winter fashion trends are you loving? Drop me a comment and let me know what you love and what you’re skipping this year!
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