50 Best Winter Outfit Ideas for Women over 50: (Formal & Casual Outfits)

Tips and styling ideas for winter dresses for women over 50.

Today, I’m sharing winter outfit ideas for women over 50, inspired by what we’re actually wearing. These ideas come from observing street style around us and from watching Leigh & Me.

Table of Contents

50 Best Women’s Winter Outfit Fashion ideas

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Both Leigh Ann and I recently dressed for a shopping trip using items from our own closets. While we can’t provide direct links to all the garments, I’ve created slideshows featuring similar pieces to what we’re wearing.

I hope you find inspiration and motivation from seeing our real outfits and gather some winter outfit ideas for yourself.

So, let’s get started!

Best Fashion For Women Over 50 – Outfit Ideas

1. Striped Sweaters And Ankle Length Trousers

Swap your unflattering oversized sweaters for chic striped knit sweaters. Stripes are versatile and suitable for all ages. Replace your baggy sweats with ankle-length trousers that strike the perfect balance between loose and tight, creating a casual yet stylish look.

Striped sweaters and ankle length trousers for women over 50

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As you know, I love wearing brooches this time of year when I have on coats and jackets. I chose a brown brooch to complement my brown sweater.

Now, let me tell you about the sweater.

I recently mentioned that I was going to try some affordable brands, which led to my posts about Quince. I also decided to try a couple of items from Amazon, not the top brands. VIEW THIS ON AMAZON

I ordered this FIXMATTI Stripe 2 Piece Outfit. Although I haven’t worn it as a set yet, I really like the sweater and have worn it at least three times.

The pants I’m wearing are the Talbots T by Talbots Ribbed High Waist Flare Leggings. They are incredibly comfortable, look nice, and I’ve worn them often.

My green crossbody bag is a beautiful BRAHMIN piece I found on sale at Dillard’s last year.

Here is a GEL Polish I USED with.

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2. Add Layers – Scarves, Cardigans

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Women over fifty often assume that this age means frumpy, without realizing it can be quite fabulous. With a few stylish additions—like tops with asymmetrical cuts, smart patterns, cardigans, and jackets—you can elevate your look. Scarves, in particular, can add a touch of class and sophistication. These accessories are not just great for women in their fifties or plus sizes, but for anyone looking to enhance their style.

3. Colors And Prints

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4. Denims For Fifties

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WINTER OUTFIT IDEAS FOR WOMEN OVER 50: STREET STYLE (SORT OF)

Style Guide And Winter Wardrobe Tips For Women Over 50

A personal stylist says, “Many 50-year-old women think the game is over and dress like teenagers to look more attractive. But today, fifty is the new thirty, and you can be beautiful and youthful by choosing items that enhance your age. What’s more intriguing and seductive than a pencil skirt that hits just below the knee paired with a pair of Louboutin heels?”

Hemlines don’t have to be too short to be stylish or too long to be appropriate. A little below the knee is perfect. Don’t shy away from bold colors; just balance them out. Opt for well-fitting jeans and trousers instead of loose, sloppy ones. Avoid pairing loose jeans with loose tops—let one piece be well-fitted. Choose dresses that drape around you rather than clingy ones. Cardigans are a better choice than oversized tops. Never underestimate the power of shapewear and the right lingerie. Select patterns and prints that complement your body shape. Accessories are and always will be game changers.

Beth Djalali, a blogger, shares her thoughts on dressing women over 50 on her personal blog. She says, “The style goal for any woman of any age should be to look modern and fresh, not dated and stodgy. It’s time we focus on style secrets for women over 50.”