Winter Fashion Over 50: Cute Casual Outfits

Last Updated on April 23, 2024 by Candi Randolph

This will be my second winter season in the Midwest, so I should have the layered look fairly well defined by now! You know…jeans or pants, long sleeves, a sweater or jacket, boots…and that’s before I head outdoors! Well, not really quite that literal, but almost.

The aforementioned wardrobe basics are the essentials of winter fashion over 50. We all have at least a few of these in our closets, so (yawn…) what’s so interesting about that?

Cute casual outfits for winter for women over 50 and over 60

Well, it’s what you do with those separates and how you accessorize them that will turn your outfit into something that is memorable, and probably will make you feel more confident, too!

Let’s take a look at some of the current fashion trends, then we’ll put together some casual outfits for women over 50 and over 60 that are cute and fun to wear.

By the way, if you click on a link and then decide to make a purchase, I may earn a small commission at no additional cost to you. Thank you!

Fall & Winter Fashion Trends

cute casual outfits for winter for women over 50

Trends in Fashion: Winter Fashion Over 50

Every year brings new trends in fashion for us, and although most of us might not dash to the store, online or walk-in, to add the latest and greatest to our wardrobe, it’s fun to see what’s trending for Fall 2020 and Winter 2021. Winter fashion over 50 at it’s best.

Our friends at TrendSpotter have pointed us in the fashion trend direction, and here is a peek at some of their recommendations:

  • Brown Leather Coats
  • All Over Neutrals
  • Blue, styled with Neutral Tones
  • Tiger Prints
  • Yellow Maxi Coats
  • Soft Hand-Held Bags in Pop Colors

I’ve curated some suggestions for you that address most of the fashion trends noted above. Check them out and maybe you’ll decide to update your wardrobe with a piece or two!


Even though we’ve moved on in time to 2022 and beyond, here are some of the 2019 Fall and Winter fashion trends, to include the types of styles the typical woman in midlife would consider wearing when putting together a cute casual outfit for winter. There are some interesting looks, including classics, that never go out of style.

If you want to see every current trendy outfit that trotted down the runway during Fashion Week, that’s cool. Find more details about the fashion trends here.

So, if you want to include some of the current trends in your cooler weather outfits, think about these. You’ll also find examples of most below, to give you some visualization:

  • Accessories and finishes with an ‘Urban Cowgirl’ feel, such as Rancher style hats, western-style boots, snake prints, and oversized belt buckles. Some or all four of these trends could look fabulous on you, or not so much. You might opt for just one, or maybe two of these accessories and let that be your style statement.
  • Animal prints, leopard in particular, as the fabric in a top, a scarf, an accessory on the shoes, or go wild and if your figure can pull it off, in the pants. For me, it would probably be a scarf at most, because that’s how I roll.
  • Plaid is in and can be found on anything from a scarf to a full-length coat. Depending on your figure and stature, you might choose a more neutral-toned plaid to keep the overall look slenderizing. But if you want to make a bold statement, go for a brightly patterned plaid jacket. Why not?
  • Denim in oversize styles is popular this season. A jacket would be the choice of most midlife women, myself included. For me, the oversized look works to a point, but I don’t want to look like I bought a jacket 3 sizes too large, either. It’s finding that stylish look that looks right, too.
  • Silk scarves are popular and quite versatile in how they can be used to accessorize an outfit. I remember when we all wore scarves with our outfits, particularly with sweaters. I’m good with this trend and will probably add a couple of pretty patterned scarves to my fall and winter wardrobe.
  • Long coats are back. I absolutely loved my long, long winter coat and wore it with heeled boots back in the day. Your overall height plays into how well you can pull off the look. I’m of average height so as long as I opt for some type of heel I’m okay.
  • Pearl hoop earrings are trending and popular. You’ll find two styles: a hoop that is literally made of little pearls, or a gold (or silver) hoop that has a pearl dangling. If I’m going to go with this trend I think I’ll opt for the hoop made of little pearls. They would make a beautiful and dainty finishing touch to an outfit.
  • Square necklines and square-toed shoes. Opt to include them in your wardrobe if you like that look and feel confident wearing it.

Winter Fashion Over 50 – put it together

Casual winter fashion for women over 50

Now that we know what’s trending this season, let’s look at some examples of the styles. I’ve gone to Amazon because of the vast selection and ease of presentation. If you’re a Prime member you can try before you buy, too, and that’s always a plus.

If you’re not sure what styles, fabrics, necklines, and patterns would complement your figure, read more about discovering your body shape. I’ve got a free printable you can keep with you that’s very helpful when shopping!

Some of these are the wardrobe essentials I mentioned earlier…the pants and jeans, the cardigans and jackets, and others are examples of a trending look for the season.

A casual outfit for cooler weather usually starts with jeans or slacks, so this is where we begin. The straight-leg look is popular now in jeans, so that is what I am showing here:

A well-fitting pair of black or dark neutral slacks are always a winner when putting an outfit together. How you choose to wear your slacks is a personal choice, and also determined by both your figure type and the styling of your top/layers.

Fortunately, dark colors are slimming so are a good choice for those of us who have a little bit of extra love in our figure:

Most of the time our cute and casual winter outfits include some type of sweater or cardigan, so let’s include these examples as part of the foundation of our style:

Most of us love a bargain, and when it comes to the wardrobe, fast fashion provides us with options for creating new outfit combinations without a big fat budget.

Target is another source of affordable sweaters and cardigans. Here is a post that I put together recently, highlighting some current Target finds:

clockwise from top left: black | ivory | dusty rose | beige | teal | leopard print | black with shawl collar | bright blue | ivory with buttons

Denim jackets are always in style, and this season includes the ‘oversized’ look. I always opt for what looks best on me, trendy or not!

If you can’t get enough of neutral plaids, here is a collection of some of my favorites. Always a classic look!

Let’s have some fun with snake prints, and look at how you can take your outfit from okay to fabulous with a cool pair of shoes. We don’t have to wear spikey heels to look trendy. 🙂

Scarves are a wonderful, flexible and economical way to add some flair to your outfit. These examples lend themselves to cooler weather!

Creating a Cute Casual Winter Outfit!

Let’s see what happens when we take a few of the separates here and create two casual outfits for women over 50 or over 60, like me. Both of the looks I’ve labeled “Black & White” are on the conservative side, so nothing outrageous by any means, and would fit well into the ‘winter fashion over 50′ category!

But there is definitely a difference between the two:

Look #1

winter fashion over 50

Details: trousers | top | shoes | necklace | earrings

The first casual look is quite nice, really. Black and white is always a good choice. This outfit is simply styled with ankle-length dress trousers, long sleeve boat-neck tunic top, black slip-on Skechers, silver ‘Love’ necklace, and double hoop earrings.

Clean and classically styled. We’re good to go.

But, what if we took it up a notch or two and added some interesting (a bit trendy) pieces? Let’s see what happens:

Look #2

cute casual winter outfit for women over 50

Details: pants | top | vest | boots | necklace | earrings

We’ve got the same trousers and tunic top, but now we’re going to switch out the Skecher slip ons for some ankle boots with just a bit of western flair.

We’ll add the buffalo check vest with draped lapel open front, and switch out the jewelry, adding a vintage-style multi-tier beaded necklace and tortoise hoop earrings.

You don’t see flashy, bold colors here, but the oversize buffalo check, the unique earrings, and chunky-heeled boots add a definite sense of style. It’s cute, casual and fun to wear. As a woman in my 60’s I’d be very comfortable with this look.

Now let’s create a couple of cute casual winter outfits using jeans and adding from there.

This first outfit is nice and easy, simple and casual, using navy and gray as the color palette:

Look #3

winter fashion for the over 50 woman

Details: Jeans | Top | Scarf | Sweater | Shoes | Earrings

The outfit stays neutral all the way, with a pretty, subtle paisley pattern in the scarf and fun, planet-themed earrings. A nice look for a cool fall or winter activity.

Now, let’s take those same jeans and top (in white instead of gray) and create an outfit with a bit more of a fashion statement:

Look #4

Jeans with leopard print jacket, a cute casual winter outfit for women over 60

Details: Jeans | Top | Jacket | Earrings | Shoes | Belt | Bracelet

We’ve taken this outfit up several notches, very simply. The leopard print jacket is the focus, with hammered metal earrings that have both gold and silver tones.

Add animal print bangles, a skinny black leather belt around your waist, black ankle boots with a unique zipper edge, and you’ve created a casual winter fashion look that is cute and memorable!

As women over 50, and over 60, we may select our clothing and accessories differently than we did when in our 20’s and 30’s. That’s to be expected. But, we don’t have to dress like old ladies, either!

Take a basic outfit of separates, add some interesting, possibly trendy finishes and accessories, and you have a cute casual outfit for winter at any age!

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winter fashion over 50 tips and suggestions

6 thoughts on “Winter Fashion Over 50: Cute Casual Outfits”

  1. Candi, what great looks!!! I am visiting some of your Amazon links to do a little window shopping and pinning til payday. That buffalo plaid vest is a great piece. Perfect for layering. And I have tabs open for several of the snake skin boots you shared. Thank you!

  2. I really love that you post on confidence as well as fashion. Please remember those of us who ONLY wear skirts and physically CAN”T wear anything but flats or orthopedic shoes. I”m disabled but I love your ideas to!

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