21 Casual Winter Staples for Women Over 50

With family reunions coming up after so long and cooler months ahead, I’m using it as the perfect excuse to revamp my closet and indulge in some stunning fashion staples from my favorite retailers. If you’re on the same boat as me and the upcoming family soireés caught you with nothing casual and chic to wear, don’t stress! 

I’m sharing 21 stunning fashion staples for women over 50 that work perfectly for almost all shapes, sizes, and personal styles!

How should I dress casually in my 50s and beyond? – Tips and Casual Outfit Ideas:

I’ll be honest; fashion rules don’t appeal to me much.

After all, we all have a different idea of what stylish looks like; we all have different body shapes, preferences, and life experiences, so following strict guidelines on what to wear in your 50s/60s is not very useful, at least not in my book.

We are all unique in our way, and in this uniqueness lies the true essence of our style, making us stand out.

I think that’s one of the best things about aging. We’ve learned what we enjoy wearing and what suits us, regardless of trends.

Still, I use a few fashion tips to enhance my everyday style.  I like to dress in classic -but comfortable- silhouettes and throw in some chic elements, mostly inspired by French style. 

My biggest advice is simple: dress in whatever feels comfortable and suits the occasion.
And with that in mind, let’s jump to these 21 fashion staples for winter 2021!

Best Casual Clothes for Women Over 50 – Winter 2021:

Simply click on any of the titles below to shop

Off the Shoulder Cashmere Sweater

off the shoulder black sweater

With a slightly asymmetric neckline, this lush cashmere sweater is a wonderful option if you’re looking to update the classic winter sweater for something a bit more glam. In addition, the fit is true to size, making it ideal for a layered outfit!

Pocket Poncho Sweater

fashion over 50 model wearing peach pink poncho sweater paired with denim

This soft peachy pink poncho sweater with front pockets from Loft is just dreamy!
If you’re a fan of Loft ponchos like I am, you’ll find this one a bit more boxy than their previous poncho styles, but it’s still the best around. I love the relaxed fit and how incredibly soft the knit is.

Cotton Cashmere Cable Knit Sweater

over 50 fashion model wearing a camel Cotton Cashmere Cable Knit Sweater

Winter calls for cozy loungewear that you can dress up or down, and this buttery-soft cable-knit sweater delivers! It comes in a neutral camel shade that will give your outfit a sophisticated touch of cold weather elegance.

Satin Button-Up Shirt

button up satin shirt in a dark night blue on a white backdrop

After years of trial and error, I found that keeping some classic transitional pieces works best for me, like button-ups made with lush fabrics to give it a more contemporary feel.
For example, this satin button-up from Open Edit has a slightly oversized fit that makes it super comfy, and the little details like the side slits and patch pocket give it a trendy twist.

Mock Neck Tank Top

black mock neck top on a white backdrop

This mock neck tank top is a total must-have for the colder season!
It gives you a sleek silhouette, not too loose or too tight, perfect for adding as a first layer. I love to pair it with a snuggly cardigan for those chilly autumn mornings.


Wearever Ottoman-Knit Cuffed-Sleeve Dress

model wearing a a line dress in a blue shade with faux-tweed details and black tights

When in doubt, throw on a knitted dress, some black tights, ballet flats, and voilá! This knitted J Jill’s sweater dress has a timeless A-line fit that’s both flattering to most body shapes and unbelievably comfortable for running errands or going out for a bite.


Polished Hoodie Jacket

Model wearing a black Polished Hoodie Jacket and white top

A crossover between a sporty piece and an elegant one, this hoodie jacket from Zenergy is a fantastic addition to your fall-winter closet. Personally, I love how the silver hardware details elevate this piece from a sporty jacket to a timeless piece.

CozyChic Lite® Circle Cardigan

By far, one of my favorites from this list! This cardi is made of a soft fabric that is snuggly and warm. It is a tad oversize, giving it a roomy fit. The length of this piece is ideal, not too long nor too short. I love how it can be worn with silk tops and leggings; it’s the just-right length.

Women’s Single-Breasted Shawl-Collar Walker Coat

model wearing a burgundy CK Single-Breast Shawl-Collar Walker Coat

If you want to elevate your winter basics, you need to add an elegant piece that you can dress down, like this fabulous CK coat. The clean lines and excellent fit make this coat a versatile option you can glam up with a dressy outfit or wear casually, with sneakers and a scarf.

Felina Athletic Pocket Legging

Lately, my favorite leggings are these lovely faux-suede Felina ones. The fabric is amazing! It’s thick enough to avoid the dreaded see-through situation but with a soft stretchy feel that it doesn’t feel stiff or bulky.
It also has slim pockets that don’t create any bulk, making it even more ideal for a comfortable and stylish outfit.

Soft Ultra-Stretch Denim Jeggings

Model wearing denim colored Ab-Solution Ankle Skinny Jeans jeggings

If you love the comfort of leggings but the look of denim, let me introduce you to the most comfortable pants you’ll ever wear. These jeggings have a fabulous fabric that is soft and stretchy like leggings, but the faux-denim has a nice weight to it, making it form-fitting. Truly, the best of both worlds!

Calvin Klein Faux-Suede Cropped Pants

model wearing black cropped faux-suede black pants from CK

Is there anything better than flattering black pants? Not really, except for a pair that blends classic and trendy perfectly, like this faux-suede pair from CK. The straight cropped leg and the faux suede fabric combo creates a stylish silhouette while keeping the elegant vibe.

Ab-Solution Ankle Skinny Jeans

As far as fashion staples go, skinny black jeans are a must-have, and my choice for this winter is this pair by Wit & Wisdom.
These dark wash jeans will give your more glamorous ensembles a casual flair while keeping you comfy.

Suede Trim Lace Up Sneakers

The delicate trims of tan suede and modern shape of this Loft lace-up sneakers strike the ultimate balance of sporty and sophisticated.
You can choose from a cream-tan or a black-tan combo. I love both options, but I’ve been eyeing the light version for a long time now. It’s just so pretty!

Sofft® Bellis III Boots

These lightweight boots are such a simple yet charming fashion piece that will update your overall winter style. The heels are low, so they’ll be comfortable for everyday wear plus, these are also waterproof. Totally worth the splurge! They come in a lovely whiskey brown shade and also in black. However, the black seems to have a more grainy texture than the brown ones, a small detail to keep in mind.

Born® Beca Ballet Flats

neutral camel ballet flats on a white backfround

These dainty ballet flats from Born are chic statement shoe that looks amazing paired with almost any outfit. These come in three stunning colors: a rich terracotta, nude, and powdery dark blue.
This model is ideal for those who need a roomy fit, as these flats run a bit wide.

Buffalo Check Blanket Scarf

We can’t talk about winter fashion and not mention a blanket scarf! This one from Madewell has a rich, warm hue mixed with black and blue threads woven through giving the classic buffalo check pattern a unique autumnal spin.

Evening Sky Short Layered Necklace

Add a luxe edge to your knits this winter with this stunning layered necklace made with beads in shades of blue and grey with metallic accents.

Calvin Klein Havana Tote

With the right bag, even the most casual look will feel polished. My number one pick? This CK Havana tote!
You can carry your laptop around in this tote thanks to its just-right size and its sturdy material.

Ralph Lauren Women’s Erica Belted Small Oblong Wrap

Equestrian-inspired, this 100% silk oblong wrap is an accessory that’s worth having around. Wrap it around your tote’s handle or make a simple loop tie around your neck for a chic finishing touch to your everyday outfit.

Macy’s Cubic Zirconia Crossover Hoop Earrings

If you’re used to wearing dainty jewelry but want to add a touch of glam to your casual winter outfits without going overboard, you need to check out these classic sparkling hoop earrings!


Now, let’s embrace our unique sense of style this winter season! I’m definitely going after the casual-chic route with these lovely fashion steples… how about you? Let me know in the comments!

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  1. Maxine Hamann says:

    What a great idea of showing age appropriate clothes! Checking out a few things to check out and order. !!

    1. I’m so glad that you approve Maxine. We definitely can still be stylish over a certain age!

  2. This is all lovely! I am many years past the 50/60 range. Guidelines for my age seem to be lacking, and I’ve decided I’m just going to follow these! Dressing thirty years younger might work better at this point.:-) I bemoan the fact that my plantar fasciitis no longer likes ballet flats! Shoes are a real challenge at this point! I read your posts daily; first response I’ve made in quite awhile! Enjoy the holiday season!

    1. Thank you Nelldean and I am glad that this resonated with you! I have very high arches and a bone spur, so shoes can be challenging for me as well. It’s just a matter of finding the right fit and then I get multiples! Happy holidays 🎄

  3. Love the outfits you put together, just lovely! I love classic cuts and have no desire to shop at the same stores as my teens. Thx for pairing leggings with tops that don’t show the rear, seriously tired of seeing women’s butts. Nothing more beautiful than an elegant woman.

    1. I’m so glad that you enjoyed this and I too do NOT want to show my behind! Aging well is an art that I aspire to and it does take work.

  4. Great roundup of instant classics! Thank you for doing the legwork.

    1. Linda A. Charlton says:

      I love these pieces. I am 73 and don’t like to dress like a frumpy old lady (which I am not). These are stylish for most ages.