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

Cute Casual Outfits for Winter – Fashion Over 50

(Last Updated On: November 4, 2019)

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 cute casual outfits for winter. We all have at least a few of these in our closets, so (yawn…) what’s so interesting about that?

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.

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Fall & Winter Fashion Trends

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.

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.

Cute Casual Outfits for Winter – 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:

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!

You’ll find some examples of leopard prints in sweaters and jackets, then several plaid jackets that I really like. The patterns vary from subtle and neutral to quite bold!

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 or boots. 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!

The pearl hoop earrings, my friends, can take a simple outfit and elevate it a notch or two. And, they are always a lovely finish to an elegant style.

The Fashion Cure - rediscover your style in midlife

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.

But there is definitely a difference between the two:

Look #1

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

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

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!

Simple neutral outfit for a woman over 60

So, now I’m going to use myself as an example. I’m wearing a casual, neutral outfit, as usual, with black pull-on Ponte Pants, a neutral pullover sweater I’ve owned for several years (one of my favorites), a simple gold necklace and earrings, and black shoes.

It’s a nice, simple look, and would typically be my choice. Nothing flashy, but probably not too memorable, either. Let’s switch out the shoes and accessories and see what happens:

Cute and colorful outfit for fall or winter

The black shoes were replaced with a tan slip-on that has some western-style accents. I added a colorful scarf in the colors that look best on me and compliment the sweater. The gold hoop earrings were switched out with a fun pair of bohemian vintage style dangle earrings, and I added a fringed wallet style purse that is small but does the job.

Casual accessories for a cute winter outfit

I like this look…still on the conservative side, because that’s who I am. But the colors in the scarf and earrings are very pretty, the purse is fun, and I love the shoes because I can wear them with jeans, too.

Here is some shopping info for you. The scarf shown is the right style in a different color. I am wearing ‘Red’. The pants are similar to mine, although the pair I am wearing was purchased at Costco:

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!

Candi Randolph Midlife Blogger


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Cute Casual Outfits for Winter for women over 50


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4 COMMENTS

  • Great suggestions. Love the pearl hoop earring! Accessories, like scarfs and earrings, are little items that can truly make an outfit pop!

    • Candi Randolph
      AUTHOR

      Hi Migdalia, thanks! You’re right, it is those finishing touches that can make all the difference!

  • leslie roberts

    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!

    • Candi Randolph
      AUTHOR

      Hi Leslie, I love that buffalo plaid vest, too, I think it’s a very versatile piece. Thanks so much for stopping by and having a look, always appreciated!

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