Warm & Cozy Outfits for Women over 50

Cuddle up for Winter in these cozy and cute outfits for women over 50. Find essential wardrobe pieces that can be mixed and matched to make lots of outfits you love wearing.

I just stumbled onto this post on Winter fashion for women over 50 that I wrote a few years ago. And, the funny thing is, I’m still wearing almost all the items that are pictured! (The white sweater had an unfortunate laundry incident!;))

I love it when I find tried and true wardrobe pieces that stand the test of time – no matter what the “trends” are!

I’ve gone through and updated the links for specific items, as many of the original ones are no longer in stock.

I hope it’s helpful for you if you are looking for some cozy and cute things, too!

Cozy Winter Outfits (that can be mixed and matched!)

Disclosure: This post contains affiliate links for your shopping convenience.

Many of you have requested information on women’s fashion and details for a Winter outfits for women over 50.

I’ve had great fun putting together seasonal wardrobes that mix and match and make me feel comfortable and pretty. My 10 piece Summer wardrobe can be found here.

Today, I wanted to share with you some of my favorite Winter Wardrobe Basics that I think are worth investing in.

Winter Outfit Essential #1 : Cute, Comfortable Shoes

My Grandma told me years ago to take good care of my feet, and when I became an old woman, I’d be grateful. I’ve been heeding her advice! Skrimping and saving by buying ill-fitting shoes is a bad idea over the long run.

I invested in a low-heeled pair of ankle boots years ago, and wear them all Winter long!

Mine are black, but I think the brown ones are really cute, too.

Here are some practical stylish low heeled ankle boots perfect for pants and dresses.


Winter Outfit Essential #2: Neutral Colored Pants

Sometimes I find it’s nice to have an alternative to jeans, so I like to have 2 pairs of dressier pants. Mine happen to be navy blue and black, but any neutral color you like would work great. They can be paired with nice tops and sweaters and can be a part of many outfits.

I recently discovered these super comfortable Pixie ankle pants from Old Navy that quickly have become a favourite. Since I’m 5 foot 2, they come right to the top of my ankle boots. If you’re taller, they may fall higher up your leg.

I love how they can be dressed up or down depending on the occasion.

Winter Outfit Essential #3: Cardigan Sweaters

I have a few different colors of cardigan sweaters that I love to wear. They can be paired with short or long sleeved t-shirts for layering.  Add a long necklace or scarf and an outfit comes together in no time!

Layering t-shirts

Layering t-shirts in basic colors are a winter wardrobe must for me. I like classic short and long sleeved t-shirts. The color I find the most versatile for me is black. It just goes with everything!


Winter Outfit Essential #4: Good Fitting Jeans

wear jeans almost every day in life! Finding a good fitting pair of jeans that makes you feel like a million bucks is very important! The ones pictured above are Old Navy Rockstar jeans mid-rise. They are a tighter fitting style in the legs. (I’m 5 foot 2 and wearing size 4 Regular.) Be sure to try out jeans until you find a pair that is perfect for you.

Winter Outfit Essential #5: A Cozy Warm Sweater

I love to have cozy, comfy sweaters to reach for on chilly days. Choose sweaters in colors and patterns that bring you joy!


Winter Outfit Essential #6: A Fun Dress

A striped dress is so versatile and comfortable! It can be paired with one of your open front cardigans, a denim jacket, or just worn alone. Adding a pair of tights and tall boots will make it warm enough to wear even on cold days.


Winter Outfit Essential #7: Scarves

By far, my favorite accessories for Winter is scarves. A whole new look can be created just by adding a different colored scarf! Choose scarves that mix and match together well with the colors you already have in your wardrobe.

Winter Outfit Essential #8: Accessorize with jewelry

The right accessories can take an outfit up a notch and make everything come together! I love long neckaces and wear them a lot.

Earrings, too, can brighten up your face and add a sparkle to your look. A classic hoop earring in gold or silver goes with any outfit.

My favorite place to buy jewelry online is Alison + Aubrey. Some of my favorite pieces are below:


Do you want to put together a mix and match wardrobe that you love?

If you want some help putting together a mix and match wardrobe that you’ll love year after year, I highly recommend the Closet Staples Outfit Formulas program. (affiliate link – Use the coupon code RITAJOY10 for $10 off!) It is what helped me learn how to put together outfits that I love year after year. It has great staple pieces worth investing in, and has outfit ideas for all 4 seasons of the year!

For more Ideas for Fashion over 50

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One Comment

  1. I love your winter wardrobe Rita. I tried for the undies but they don’t ship to Canada 🙁
    I’ll hunt up where in Canada I can purchase them. The open sweater looks soft and great too!

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