How To Master Fall Fashion for Women Over 50

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The temperatures are starting to dip and the leaves are losing their bright green hue. Do you know what this means? Fall is coming! And with fall comes stylish layers, cozy fabrics, and warm golden colors. Dressing in summer is usually a bit easier, you can just throw on a dress and go, but the fall season usually requires a bit of extra thought, especially if you are a woman over 50. You may be feeling that the current fall styles of today, such as off-the-shoulder sweaters, thigh-high boots, and plaid mini skirts are a little behind you, so in this post, I’m going to help you master fall fashion for women over 50 with style tips and outfit ideas!

How to master fall fashion | Fashion tips

Just because you turned 50 (or 60, 70, or 80), it doesn’t mean you aren’t interested in looking good anymore. In fact, this may be the time you can look your best as you might have the most time and resources to devote to it now! A woman over 50 still loves fashion and still wants to put her best foot forward. And there’s no reason why you can’t!

A woman over 50 doesn’t want to be told what to do. For the most part, she knows what she likes and what she wants, she just desires some guidelines and inspiration to help her get there.

When mastering fall style, I find it best to adopt classic style to look polished and timeless, but don’t be afraid to add a few fall trends to your classic look. You don’t want your wardrobe to be full of fashion trends, of course, but a few trendier pieces here and there is a great way to update your overall look and have some fun this fall season!

Keep in mind that there are things beyond what you’re wearing that can help you master fall fashion. First, think about your hair. The right haircut and style is the best accessory you can have that you can’t buy at Nordstrom! Consider this your friendly reminder to take a good hard look in the mirror and see if it’s time to book an appointment with your hairdresser. Is your current haircut flattering to your face shape? Does the color complement your skintone? If you’re not sure, then book an appointment anyway and get an honest opinion about what could be better. The right haircut will seriously transform the way you look, and in turn, transform the way clothes look on you.

When it comes to makeup, some women like to scale it back a bit when they reach 50. It’s all personal preference, but there are some very minimal things you can do to add a little bit of life to your face, such as mascara, blush, and a lip color. This routine can take less than 5 minutes and add some color to your face without making you look like a different person.

At the end of the day, let your personal style shine. Are you the woman that always has color on her lips or a scarf on her neck? Do you always leave a subtle amber smell in your wake? These small details are what set you apart!

How to master fall fashion for women over 50 | Things that should be in your closet

When shopping for clothes to add to your fall wardrobe, keep in mind the guidelines for your body type (apple, pear, etc), not to restrict you, but to help you highlight your best features. For example, if you have an apple shape, then a v neck can be very flattering on you and that may sway your decision when shopping for sweaters!

What about bright colors? Personally, I think it’s time to put the bold colors away for the season and instead, swap them out for their subdued counterpart. If you like bright orange, then opt for burnt orange. If you like neon yellow, choose mustard yellow instead. These are all great colors that can make your fall outfit shine!

These fall colors can complement your fall wardrobe, but to be able to maximize your wardrobe to its fullest potential, you’d want to make sure your most staple pieces are mostly neutral. For example, a utility jacket should be in its classic army/forest green color instead of pink.

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Oversized blazer

Oversized blazers add that perfect touch of casual style to your look. And yes, I think a woman in an older age group can still wear this item! To pull it off, keep in mind that you still want this item to be generally fitted. An oversized blazer on you should be a bit longer and looser, but not sloppy and slouchy all over. Also, you should pair this oversized blazer with fitted jeans and a fitted top. Of course, you know what looks best on you, so if you feel an oversized fit is not for you, then a blazer jacket is a good alternative that still reads as casual chic.

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Denim jacket

A denim jacket makes the perfect transitional piece when the weather starts to get a little cooler. Denim is a great material to have in your wardrobe as well. It can “ground” a look but also add some color at the same time!

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A year-round staple, but especially a staple in the fall! Not only will this item keep you warm, but it will add that extra layering piece to your outfit to make it more interesting. Come fall, push your fitted cardigans to the side of your closet, and instead, look for one that is slightly chunky and in a cozy, knit fabric.

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Leather jacket

Some women may feel this investment piece is not their style, and that’s okay, but don’t feel like it’s not for your age! Pieces like a leather jacket and a leopard print bootie will add style and sass to your look. You’ll wow people with your style abilities! This edgy black jacket can be worn with jeans or over a dark floral dress.

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Trench coat

The trench coat is a timeless piece that will add a Parisian flair to your outfit. This light layer is great for fall and will go with anything in your wardrobe. Wrap a scarf around your neck to look très chic!

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Utility jacket/Anorak jacket

A popular piece for all ages, this jacket will be sure to update your look without making you look like you’re trying too hard to be young. Pair with dark blue or black denim, a sweater, and leopard print flats for a look that is equal parts stylish and comfortable!

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Animal print coat (or other items)

If summer is the season of lightweight fabrics, then fall is the season of prints. Camo, plaid, herringbone, and of course, animal print. A woman over 50 should definitely have her stash of animal print to pull out every now and then. Whether it’s on a larger scale like a faux fur coat or on a smaller scale like booties, this is a surefire way to add interest to your look. Trust me, coming from a woman in her 20’s, you’ll surprise those around you and they’ll be saying, “Wow, did you see so and so’s mom? She dresses really stylishly!” 😉



The perfect sweater for fall is one that will look great and be warm on its own, but not so thick that you can’t layer something like a button-down underneath it. Your sweater may be your most worn piece this season, so find one that is equally stylish and versatile! You want your sweater to have enough details to make it interesting, but not so many details that you can’t mix and match with it. A cable-knit sweater, medium-weight knit, or cashmere sweater are all good options. A turtleneck sweater can be another good choice if you already have the basic sweater.

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Tank top (or basic layering piece)

This item can be worn under an open cardigan or under a top as a way to hide your bra and keep everything looking smooth. If you don’t like wearing tank tops, then a basic white top or white shirt is your alternative to this versatile layering piece. Once you have white, consider getting your basic piece in different colors. J.Crew Factory runs a lot of sales on their basic pieces!

Denim/chambray shirt

This particular piece makes a great item for fall because it works with all of fall’s colors and prints. This top, preferably long-sleeved, can be worn with everything on this list! Try wearing it closed and as a shirt of its own or layer it open a basic tee, sweater, or tank top.

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Dark denim

Skintight skinny jeans are not the style I’d recommend for you when there are so many other current jean styles that are classic and more flattering! Try straight leg, slim leg, or boot cut, either in a mid-rise or high rise. At your age, you don’t want these to be too baggy on you either. You’re after the perfect fit!

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Well-fitting pants

Come fall, women are looking for comfort. After all, the weather is getting colder and people are getting ready to hunker down. Thankfully, there are pant styles these days that look fancy but are really comfortable. Praises be! A pull-on waist has come a long way, and twill pants add just that right amount of formality to pass as real pants without losing the comfort of something like sweats. Treat these pull-on pants as normal, wearing them with everything from chunky cardigans to sweaters.

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Black pants

In spring and summer your go-to may be white, but in fall and winter a black pair of jeans (or pants) is a must! Black pants look great with camel brown, leopard print, army green, stripes, chambray, and well, everything!

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Sweater dress

Everyone needs a feminine piece in their wardrobe that makes them feel pretty. Some of the most flattering styles for a woman over 50 are a knee-length wrap dress, fit and flare dress, or sheath dress. For fall, choose one in a cozy sweater fabric or dark jewel tone.

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Longer skirt

While the younger generation may be wearing mini skirts, you’ll find yourself much more comfortable in a long skirt, such as a maxi skirt, midi skirt, or even a knee-length skirt. Find the style that works for you, but keep in mind that it’s easy to look frumpy in a maxi skirt. Try to keep your top half fitted.

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Leather leggings

You may be surprised to see this on the list, but I think a woman over 50 can definitely wear leather leggings, with a few style reminders, of course! First, leggings are not pants. Any top or dress you wear over it should fall well below your thigh and maybe even close to your knee.

Second, your leggings should pretty much be skin-tight. Baggy leggings are a no-go. I recommend the faux leather Spanx leggings. A little pricey, but I have them and can honestly say that they slim down your thighs like magic! Who doesn’t want that?

Leather leggings can be worn with sneakers and a tunic top for casual outfits, or with ankle boots and an oversized cardigan for something a bit more casual chic. If you’re dead set against the idea of leather leggings, then try leather pants instead.

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Stylish sneakers

Women of all ages, and especially women over 50, want comfort as well as style. And who says you can’t have both? Look for a pair of stylish fall-appropriate sneakers to add to your wardrobe. These will be great for running around with grandkids or walking around the garden center picking up mums for your porch.

Shoes are where you have the opportunity to really master your fall style and bring it home! Coming from a woman in her 20s, I’ll be honest and say that many people my age don’t really expect 50-year-old women (and beyond) to have cool shoes! A killer pair of boots (it doesn’t have to have a killer heel) or stylish pair of sneakers will go a long way in updating your look.

However, I know that due to foot pain problems, some women have limited options when it comes to their footwear. Health and comfort come first. If you have to buy a shoe that you feel is less than cute, then try to make it as neutral and plain as you can and bring all the style through your outerwear and accessories!

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Stylish flats

Leopard print loafers, black leather ballet flats, or mule slides are all great options when it comes to fall footwear. Before it gets real chilly, these shoes will be on your feet the majority of the time. Make them worth it!

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Ankle boots

Ankle boots are one of the most versatile shoes you could have for fall! Whether you go heel or no heel, look for a pair that is classic yet current to easily update all of your looks.

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All-season boots

Slightly different than an ankle boot or bootie, these all-season boots are more utilitarian in nature, helping protect you against the weather elements. Not only that, but they add a certain edge to your look. These boots would be Chelsea boots, combat boots, or something like Doc Martins.

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Knee-high boots

Also known as riding boots or equestrian boots, these boots come and go in terms of popularity, but they will always be a classic in my opinion and it’s worth having a pair in your wardrobe. Look for black or brown leather for long-lasting quality and versatility. To update the riding boot style, I’d recommend a slight heel (if you find that to be comfortable) and a tighter fit around the calf.

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If there’s one accessory you need for fall, it’s a scarf. This item can be the final piece to pull your whole outfit together! Not only is it stylish and age-appropriate, but there are so many different styles out there that can work for every outfit.

Gold jewelry

You don’t need a lot of jewelry to look put together and if you had to only buy 2 items, it should be gold hoop earrings and a gold pendant necklace. These items will never go out of style and will add the perfect amount of class to your look.

Leather bag

A tote bag looks a bit more casual while a handbag can be a bit classier. A crossbody bag can be right in the middle. You may find that your wardrobe needs a variety of bag styles to fit your variety of outfits. Find the style that works for you, but try to buy the best handbag you can! This means no peeling faux leather or cheap hardware. The wrong bag can really bring down your outfit-and we don’t want that!

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Below are a few outfit ideas I put together using some of these items that I feel are appropriate for older women while also possibly pushing you outside your comfort zone a little. 😉

fall fashion outfit ideas women over 50
fall fashion outfit ideas women over 50
fall fashion outfit ideas women over 50

Did you enjoy this post on fall fashion for women over 50? For even more tips to master your overall style, check out the posts below!

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Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.