This is the time of year when we’re pretty much done shopping for winter and not quite ready to think about spring fashion, so I’ve been updating some of my old 5 Ways To Wear posts to help us get a little more mileage out of our winter wardrobe essentials, and today it’s all about the grey sweater! Not only am I sharing 5 ways to wear this versatile piece, I’m showing both of the looks—Then and Now—and how I updated them for 2025!
Every woman probably has a grey sweater or two, so you can probably shop your closet and recreate these looks without buying anything new, but I’ll still link up what I’m wearing under each picture. And if grey isn’t your thing, you can substitute another neutral like ivory or camel or taupe for most of these looks.
You may also like: 5 Ways to Style a Camel Coat and 5 Ways to Style a Black Vest. Also, Then and Now: Grey Denim + Burgundy Sweater.
5 Ways to Style a Grey Sweater Redux
I published the original 5 Ways to Style a Grey Sweater back in January of 2020, and I wrote a post for each outfit, but this time I’m putting them all together in one post for easy reference. I also updated those 2020 looks in 2022, so I’m going to include those all here, as well.
#1. Then: Mom About Town
For my first outfit, I was going for a casual-chic monochromatic look. I styled a grey cashmere crewneck sweater with a black puffer vest, inky black skinny jeans, and grey/black trainers. I don’t think I wore those sneakers very much, although I distinctly remember them and trying to make them work with casual outfits. All that to say, I’m not sure I really loved this look at the time, and I definitely don’t love it now.
THEN (2020): grey crewneck sweater // black skinny jeans // grey trainers // black puffer vest
I updated that look in 2022 with this next outfit, which still looks fairly current, although the length of the jeans looks a little off to me now. Those Fidelity jeans were a slim straight ankle jean, which looks more like a crop by today’s standards, but the washed black finish adds a nice updated touch (as opposed to the more dressy black skinnies in the original look), and the VEJA Esplar is a shoe I still have in my closet.
THEN (2022): grey turtleneck sweater // washed black slim straight leg jeans // VEJA sneakers // black puffer vest
Now: Mom About Town
For today’s look, I pulled out my AG Mari slim straight ankle jeans in the washed black. These are about two inches longer than the Fidelity pair wore in 2022, and they look more modern to my eye, even though the trends lean more towards relaxed silhouettes right now. I feel like this cut is more flattering on me than the wider, more relaxed straight leg styles.
NOW: Caslon Rib Turtleneck (S) // vegan leather puffer vest (S) // AG Mari (29) // adidas Spezial (8) // rag & bone belt (M) // similar bag // swirl bangle bracelet // chunky hoops
To that, I added my vegan leather puffer, which is a very of-the-moment look—not just because of the vegan leather, but the puffier puffer (lol) makes it look more current than the older ones above.
I almost wore the same VEJA sneakers, but I decided to change it up with the adidas Spezial, since gum sole shoes are having a moment. My jeans are kind of a safe choice, and the turtleneck is pretty classic, so adding a trendy shoe keeps the look fresh and modern.
The chunky accessories (swirl bangle bracelet and chunky hoops) also help to update the look, and I made sure to wear a belt, as that adds a polished touch and belts are very much on trend right now.
#2. Then: Winter Date Night
The second outfit in the original series was a winter date night look with a grey turtleneck, coated denim, and a statement coat. (I didn’t keep the leopard coat. As I said at the time, it was just too over the top for my understated sense of style, and I don’t live the life of the woman that owns that coat… Which is still true!) And it certainly doesn’t look as fresh and fun to me now as it did at the time. That was the height of leopard everything, as I recall.
I’m also cringing at those coated black skinnies paired with the burgundy suede pumps, and the long layer necklace also dates this look. Isn’t it funny how our eyes adjust over time?
THEN (2020): coated black skinny jeans // grey Equipment turtleneck (S) // burgundy suede pumps // leopard faux fur coat // long layer necklace
In 2022, I recreated that outfit with my Vince Crop Leggings for more of an upscale look and feel. I also went with a v-neck sweater instead of a turtleneck, and a shorter black faux fur jacket instead of the long leopard print coat. I changed up the jewelry quite a bit here, as well—I went for a crystal teardrop earring with an understated bezel station necklace. And I still added a burgundy suede pump, but this outfit looks a little more classic to my eye.
THEN (2022): Vince Weekend V-Neck in Steel (S) (budget option) // Vince Crop Legging (M) (option) // burgundy pumps (8) // faux fur jacket // crystal drop earrings // bezel station necklace // link bracelet
Now: Winter Date Night
For my updated look, I actually have two—I recreated both! For the 2020 outfit, I swapped out the coated skinnies for a pair of coated flares, and I actually still have that Vince v-neck sweater, so I wore that again here.
Vince Weekend V-Neck in Steel (S) (budget option) // KUT from the Kloth Ana Coated Flare Jeans (6) // Stuart Weitzman Naomi Bootie (8.5) // Sanctuary faux fur jacket (S) // triple chain necklace // swirl bangle bracelet // chunky hoops // Hammitt VIP
My Sanctuary faux fur coat is a nice update to the one with the chevron pattern, and rather than a pop of color in the shoe, I went for a dramatic suede pointy toe kitten heel sock boot. These are a major splurge, and I’m having trouble finding a similar for less option, but I went ahead and photographed the look because I think this shows a more modern look than a pop of red against an otherwise monochromatic look. That’s not as much of a thing right now. I do have red shoes, but I like them better to dress up my blue jeans and more casual tops than with an all black outfit. (See an example HERE.)
Here’s the look without the jacket. I added a triple chain necklace and the swirl bangle bracelet and chunky hoops, as well as the belt, so it’s a complete look even without the coat. And I carried my Hammitt VIP crossbody as a clutch. I think the textured leather and edgy gunmetal hardware adds a nice extra something to the outfit, but I can also see adding a pattern or a lighter color bag to break it up.
I also did a similar look to the 2022 look with black pants, but this time instead of the Vince Crop Leggings, I wore the SPANX Perfect Fit Ponte Flare Pants. And in keeping with the original outfit, I went with a bold red kitten heel slingback—although the pop of red with an all black outfit isn’t really a current look. The shoe itself is current, but I would probably opt for my black croc-embossed Vince kitten heel slingbacks with this outfit instead. The croc embossed texture adds a nice detail to the look without drawing all the attention to the feet, and it keeps the look monochromatic.
Vince Weekend V-Neck in Steel (S) (budget option) // SPANX Perfect Fit Ponte Flare Pants (M Petite) // Sam Edelman Bianka Slingbacks in Deep Scarlet (8.5) // Sanctuary faux fur jacket (S) // triple chain necklace // swirl bangle bracelet // chunky hoops // Hammitt VIP
Which look do you like better—the coated denim or the pants? I feel like I’m a little over the coated denim. I feel like the pants look more modern, and I like the quiet luxury aspect of this second look… but probably with the textured slingbacks or the suede booties from above.
#3. Then: White Denim for Winter
For my third look, I styled a grey sweater and white jeans outfit for fall or winter, and I added a plaid blanket scarf and snakeskin booties for color and texture. Oh, how I loved those snakeskin booties, haha! They look so dated to me now, but they were good boots in 2020… And the fitted denim jacket is definitely a blast from the past, as well.
THEN (2020): Vince Camuto denim jacket // grey cashmere crewneck // white skinny jeans // snake print booties // plaid scarf
In my 2022 update, I changed out my white skinny jeans for cropped flares, and I went with neutral booties instead of the python. I also went with a slightly longer and more boxy denim jacket, and I went way overboard with that scarf! My word.
THEN (2022): Plaid Scarf // Reformation sweater (M) // Mother Insiders (28) // Marc Fisher Alva Booties (8) // KUT from the Kloth Jacqueline Denim Jacket (S) // Gucci sunnies (option) // similar tote (option)
Now: White Denim for Fall/Winter
For my modern update, I went a whole other direction and ditched the denim jacket entirely. A denim jacket with a cashmere sweater and scarf looks incongruous to me, and denim jackets aren’t as much of a thing right now. If they are, they are big and oversized—a look I’m not crazy about. So I went with a long wool coat instead. This looks way more current to my eye.
similar grey coat (S) // similar sweater // PAIGE Leenah Trouser Jeans (29) // Aquatalia boots (8) // similar belt // chunky hoops
Not only is the style of the coat more current, but the monochromatic look with shades of grey and white really keeps it fresh and up-to-date.
And the white trouser jeans are a nice update to the crop flares and white skinnies, especially for winter. I happened to have a pair of taupe booties I’ve kept around, and they work perfectly with this, but I don’t have a link because they’re from last year or the year before.
And because I wore a scarf in the original looks, I did throw on my Burberry scarf just for the fun of it—this would make more sense with the coat, of course! We thought about it after we got back inside.
#4. Then: Cozy & Casual
The 4th outfit in the original series was a super casual look with a puffer jacket, ripped jeans, and hiker boots. I really like the combination of the light wash jeans, medium grey sweater, and grey hiking boots; and the washed red jacket is a fun pop of color.
THEN (2020): grey Equipment turtleneck (S) // MOTHER Looker Ankle Fray Skinny Jeans (28) // Caslon hiker boots // REI red puffer
When I updated that look two years later, I didn’t have grey boots, hiker style or otherwise, so I went with my go-to fashion sneakers at the time. I chose a more muted color for the puffer jacket, but it still adds a nice contrast of colors to the otherwise neutral look. These jeans were supposedly more of a slim straight than a skinny, but they still look pretty skinny!
THEN (2022): grey Equipment turtleneck (S) // AGOLDE Toni slim straight ankle jeans (28) // P448 John (39) // Barbour puffer jacket // pearl earrings // link bracelet
Now: Cozy & Casual
I actually don’t have a short puffer jacket right now, believe it or not! And the only casual jacket I have in a color is my red Helly Hanson insulated rain coat, which is sold out, so I decided to wear the color in my shoes, and I just wore a black quilted vest over the turtleneck sweater. I actually still have the Equipment turtleneck I’m wearing above, but I decided to shoot this look with a more accessible option—this Caslon ribbed turtleneck in the dark grey heather. (It’s low inventory, but the medium grey heather is fully stocked.)
Caslon Rib Turtleneck (S) // Cooper Quilted Vest (S) // PAIGE Leenah Ankle (29) // PUMA Easy Rider Vintage (8.5) // chunky hoops
These PAIGE Leenah wide leg ankle jeans are a new wardrobe addition, and I think they’re really fun with sneakers, for a change from my usual slim straight ankle jeans or long flares. They do add some visual weight but when I keep the rest of the outfit in proportion, I think it works.
And while the “pop of red” isn’t as much of a thing right now, I like it better with the sneakers and blue jeans than I do with the slingbacks and all black outfit. I think I’d like it even better with lighter colors on top… maybe a white jacket on top of that grey sweater?
#5. Then: Monochrome with Pop of Red
Here we are again with the pop of red… haha! I ended that series back in January 2020 with this monochromatic winter date night outfit. I paired suede over the knee boots with black skinny jeans, and I wore a classic cashmere crewneck with my leather moto on top. Then I added a red crossbody with silver chain detail for a little pizazz. I actually really like the red bag on this look, rather than in the footwear… and I sure do wish I’d kept that bag.
THEN (2020): grey cashmere crewneck (S) // AG Farrah (28) // Bernardo leather moto // Stuart Weitzman OTK boots // Michael Kors crossbody
I just didn’t reach for it much, and it eventually made it to the donate bin. Now, I realize, I don’t even have a red bag. I think I need to remedy that. Also, I really loved that leather jacket, but it started to look worn and I passed it on, as well.
To change things up a bit in 2022, I wore my black skinnies with knee boots instead of OTK boots, and I went with a faux suede moto rather than the leather jacket, although I still had all the components of the first look at the time. I actually still really like this outfit, but doesn’t feel as fresh and modern as it did then.
THEN (2022): grey cashmere crewneck (S) // AG Farrah (28) // Sam Edelman boots (8) // KUT from the Kloth Quinn Faux Suede Moto (S) // Michael Kors crossbody
Now: Monochrome with Pop of Red
Since I don’t have a red bag, I recreated this look with red shoes, but as I said before, we aren’t really doing this right now… the monochrome with pop of red thing. I mean, you certainly can if you like it, but the purpose of updating these outfits is to show something that looks more current, so I can’t say this is my favorite of these looks. I even tried it back in the fall with this casual look, and I think it works better with the blue jeans, but I still felt at the time that my feet were arriving before I did. I think I will like them better with grey or white on top. The red and black creates such a stark contrast.
AllSaints Orten Leather Bomber (8) // Caslon Rib Turtleneck (S) // PAIGE Leenah Trouser Jeans (29) // Sam Edelman Bianka Slingbacks (8.5) // rag & bone belt (M) // similar bag // chunky hoops
These shoes worked really well with this outfit, by way of example. That’s how I would do a pop of red with the slingback pumps today.
Sanctuary stripe sweater (S) // similar jeans // Sam Edelman slingback pumps (8) // hinge bracelet // similar hoops // necklace set // Coach bag
Bonus Looks
You know me, I can never leave well enough alone, so here are a few more looks with grey sweaters that I’ve worn lately…
This cardigan sweater is a very light grey, and I love how it looks paired with the darker grey flare jeans. (Sorry, I now it’s spendy! I got mine on sale, and I expect it will go on sale again… maybe even for President’s Day Weekend. I’ll keep an eye on it.
The monochromatic look is very much on trend, as is the short v-neck cardigan worn as a pullover, as shown here. The black boots are a little heavy, but I like how they work with my hair to bookend the look. For a lighter look, I could try those taupe Aquatalia boots with this.
Vince Donegal Cardigan (S) // MOTHER Weekend Flares in Wanted! (29) (option) // similar boots
And both of these looks feature a grey turtleneck, blue jeans, black boots, and a black vest. It’s an outfit formula that I repeat over and over again.
LEFT: similar sweater // Cooper Quilted Vest (S) // MOTHER Weekender in Layover (29) // similar boots // similar belt
RIGHT: Halogen Funnel Neck Sweater (S) // Rowan Puffer Vest (S) // PAIGE Laurel Canyon Flares (29) // similar boots (8) // similar belt
