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 reworking 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!

I figure every woman probably has a grey sweater or two, so hopefully you can shop your closet and recreate these looks without buying anything new, but I’ll still link up what I’m wearing under each picture.  

5 Ways to Style a Grey Sweater Redux

I published the original 5 Ways to Style a Grey Sweater back in January of 2020, so I still have some of these pieces, but I tried to tweak each look a bit to make it fresh and modern. And if grey isn’t your thing, you can substitute another neutral like ivory or camel or taupe for most of these looks. I personally love a great sweater, and I have a few so I used a different one for each look.

Outfit #1: Mom About Town

For my first outfit, I styled a grey cashmere crew with a black puffer vest, black jeans, and grey/black trainers. I was going for a casual-chic monochromatic look. Because the look is casual, I didn’t bother with a necklace, but it could probably use one — or a scarf is an option as well.

Outfit #1 Update:

I shot a whole new look for this one because I love this combination so much. I realize not everyone shares my love for grey and black outfits, but this is such a classic look that never gets old for me.

grey turtleneck (M; similar option/splurge option/budget option) // faux leather vest (sold out; option) // Fidelity denim (28; budget option) // belt (M) // Vejas (39; option) // sunnies (budget option) // similar tote

I swapped the crewneck for a turtleneck because I like the look of a turtleneck with a vest. Plus, I don’t usually wear a coat when I wear a vest, so any extra warmth is appreciated!

If I had gone with the crewneck, I would have tried one of my shorter layered necklaces like this mixed metal set of 3 by Madewell, but I decided to go without a necklace in this case. This overall look is casual, and my longer necklaces that would fit over a turtleneck seemed too dressy for this outfit. The long pendants are looking a little dated to me at the moment, anyway.

I did add a belt, though. It’s such a small detail, but I feel like this outfit really needed that extra point of interest.

These jeans are Fidelity Denim, and this slim straight ankle silhouette in the washed black looks more modern than the jet black skinny ankle jeans from the 2020 look above. A similar style for less would be the Madewell Perfect Vintage Jeans or maybe their Stovepipe Jeans.

Unfortunately, my faux leather vest sold out a while ago, and I haven’t been able to find much like it, but any regular puffer vest would work with this look. Finally, my Vejas with the black accents complete the look. The Adidas Superstar would achieve the same effect.

I know some of you are cringing to see my bare ankles in January, and you could totally wear socks with these. I typcially don’t bother because I’m lazy (and apparently impervious to cold) but a grey crew sock would tie into the sweater, and the low contrast of the grey with the white sneaker wouldn’t look too out of place. I’ll have to try that next time.

Outfit #2: Winter Date Night

The second outfit in that series was a winter date night look with a grey turtleneck, coated denim, and a statement coat. I still like this outfit, but I didn’t keep the leopard coat. 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.

Here’s how it looks without. Still cute — that necklace really does look nice on the turtleneck for a dressier vibe, the coated denim takes it up a notch, and the burgundy suede pumps add a subtle touch of color to the otherwise monochromatic outfit.

Outfit #2 Update:

I still have those coated jeans from White House Black Market, but since I don’t have any looks with non-denim pants in this collection, I decided to recreate the outfit with my Vince Crop Leggings for more of an upscale look and feel. I also went with a v-neck instead of a turtleneck and a shorter black faux fur jacket (similar here).

grey v-neck sweater (S; budget option) // black pants (M; option for less/budget option) // burgundy pumps (8) // faux fur jacket (sold out; option) // crystal drop earrings (option) // bezel station necklace // link bracelet

I’ve talked a lot about these pants, and they’re definitely an investment, but the fabric is amazing and they are so flattering. I always recommend the Spanx skinny pants as a more budget-friendly alternative, and I also found this option at Express.

Here’s the look without the jacket. This is the Vince Weekend V-Neck, which I managed to grab on a really good sale a few years ago right after Covid hit an all the stores were practically giving stuff away. I chose the v-neck instead of the turtleneck because it seems dressier, and the turtleneck is really long. I like the proportions of this outfit better with this sweater.

Finally, the Sam Edelman pumps in the Bordeaux suede brighten up the look, and the crystal drop earrings add sparkle and shine. Because they’re the statement piece, I went with a delicate bezel station necklace. Both are sold out, unfortunately, but you get the idea!

This would make a really nice outfit for a Valentine’s dinner out, don’t you think?

Outfit #3: White Denim for Fall/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.

I loved those boots so much; not only did I love the snake print, but they were so comfortable. Unfortunately, that style is looking dated to me now, and while python is a classic in footwear, it was so trendy for a short time that it’s a bit tired at the moment.

Here’s how it looks without the scarf, by the way. I added a long pendant for a focal point.

As I pointed out in that post, it may be too cold where you are to wear this outfit right now, but it’s a great look for fall or early spring, and you can ditch the denim  jacket and wear a coat for now.

Outfit #3 Update:

I shared this outfit last week, so you can get more details on it there, but basically I changed out my white skinny jeans for cropped flares, and I went with neutral booties instead of the python.

Madewell Barwell Plaid Scarf // Reformation Cashmere Blend Sweater (M) // Mother Insiders (28; budget option) // Marc Fisher Alva Booties (8; option) // KUT from the Kloth Jacqueline Denim Jacket (S) // Gucci sunnies (option) // similar tote (option)

I also purchased a new scarf since the one in the look above is no longer available. I think this one has a more wintry vibe than the one above, which reads as more of a fall look to me.

I also like this look without the denim jacket, but I do feel like the proportions are a little off. I wish I had given the sweater a front tuck, or better yet, worn longer jeans. The Mother Hustler is the same style, but with an extra inch or two and a straight raw hem as opposed to the step hem, and KUT from the Kloth has this full length pair that I really want to try.

Outfit #4: Cozy & Casual

This is 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 nice pop of color.

Outfit #4 Update:

I don’t have grey boots right now, hiker style or otherwise. And while lace-up styles are very popular at the moment, I always feel like they look a little too utilitarian on me, so I decided to recreate this look with my go-to fashion sneakers.

The difference in the denim is subtle, as the wash is similar, but these are a slim straight style with a 26 1/2″ inseam and 13″ leg opening, as opposed to the skinny ankle jeans (28″ inseam + 10″ leg opening) I was wearing in the look above.

And I still have that red jacket, but I haven’t reached for it much this year. I decided to photograph this updated look with my Barbour puffer in the trendy latte color. I really like this soft color palette for this time of year.

grey turtleneck (M; similar option/splurge option/budget option) // AGOLDE Toni slim straight ankle jeans (28; option/budget option) // P448 John (39; option) // Barbour puffer jacket (US6) // similar pearl earrings // link bracelet

Outfit #5: Monochrome with Pop of Red

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.

I added a red crossbody with silver chain detail for a little pizazz. The hardware has a more rugged/edgy vibe than most of my other bags, and I like the element of interest it adds to the look.

I still have every piece to that outfit, but in order to change things up a bit, I wore my Sam Edelman knee boots with my black skinnies, and I went with a faux suede moto rather than the leather jacket.

grey cashmere crew (S) // AG Farrah raw hem ankle skinnies (28; budget option) // Sam Edelman Sulema Boots (8) // KUT from the Kloth Quinn Faux Suede Moto (S) // similar crossbody (more options) //

The red bag really pops this outfit. I picked this up at the Michael Kors store in my local mall a few years ago, and I don’t carry it nearly enough. It’s a gorgeous bag.

Even though booties are having a moment on the fashion scene and over-the-knee boots are waning, I still like a classic knee boot. It’s more of the moment to pair them with a midi skirt or dress, but I feel like this outfit has a modern classic look to it that works for my personal style and also the area where I live.

I do wish I’d taken a picture with a straighter jean and black booties, just for the sake of showing more options. It didn’t occur to me at the time.

And that’s it for this year’s 5 Ways to Wear a Grey Sweater. For even more outfit inspiration, check out all of my 5 Ways to Wear posts, and you may also like my Winter Wardrobe Essentials.

Stay In Touch

If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.

I would also love for you to join my JLS Fashion Insiders Facebook Group! This is a safe place to discuss all matters of fashion and style with other women, share your outfits, and get advice, and stay up to date on all the happenings in this community.

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!