5 Fall Wardrobe Essentials for Women Over 50

It’s hard to believe that summer is ending, but here we are! Halfway through September, and just like that, the warm weather is starting to subside here in beautiful Vancouver, Canada. We had a blast on Vancouver Island this past weekend, and I noticed the leaves are starting to turn, which has me thinking about fall and all the things I forgot to pack. Today I’m sharing the 5 fall wardrobe essentials for women over 50 that I rely on when the weather changes.

fashion blogger jennifer connolly wearing wide leg jeans

These are pieces that you’ll reach for again and again, year after year, as the weather turns from warm and breezy to cool and brisk. I love shopping for fall because I get to reach for some of my favorite pieces.

What five pieces should be in your fall wardrobe? Let’s dive in.

A Comfortable Flat Boot

fashion blogger jennifer of a well styed life wearing fall wardrobe essentials for women over 50

Not many of us are reaching for heels these days, but even if we weren’t dealing with the pandemic, a classic fall staple is a comfortable flat boot. I’m a big fan of a riding boot, especially one that is waterproof and flat. This is a classic boot style that you can wear year after year, under a long skirt, or with jeans or leggings tucked in. Mine is an investment (La Canadienne) but I’ve had them at least ten years, and are still in great condition and totally in style.


fashion blogger jennifer fo a well styled life wearing halogen cashmere cardigan and good american jeans

A cardigan is a great piece for layering, especially when the weather is still turning. I love how versatile they are and you can pair them with pretty much anything –  a pair of jeans, over a dress, open and belted. My latest favorite is this beautiful long cashmere-blend cardigan in a soft neutral grey. Even though I’m short, I love the look of the longer duster length. Whether you prefer a long duster, a classic button-down, or a boyfriend-style… a great cardigan is essential for your fall wardrobe.

A Modern Jean

over 50 fashion blogger Jennifer Cobbolly wearing rose colored shirt and blue jeans
BLOUSE on saleJEANS on saleEARRINGS on saleSANDALS on sale

I am a big fan of a great pair of jeans, and I buy a new pair (at least) each fall. My favorite style this year is high-rise straight jeans. In fact, the high-rise has been my favorite for years because they control muffin top:) Trend reports are saying the skinny jeans are dead this fall, but I can’t imagine they’ll ever go away!

fashion blogger wearing j crew blouse and NYDJ wide leg jeans

I think it’s also fun to buy a new trend that catches your eye, which helps keep your look modern. I’ve dabbled a bit in the wide-leg style I’m seeing around lately as well. They’re a fun style, and it’s all about finding the right proportion for your shape. I believe in owning a pair or two of investment jeans that will stand the test of time. This fall I have my eye on a pair of beautiful Frame jeans that fit wonderfully on me.


A Casual Flat

A comfy and casual flat is mandatory for everyone’s fall wardrobe. I love the classic shape and elegance of the AGL ballet flats. They are an investment piece, but you’ll have them for years. My daughter and I have both owned these for many years, re-soling them when needed. They can be easily dressed up or down.

over 50 style blogger Jennifer Connolly wearing double denim

A driving moc a (loafer with a rubber sole) is a comfy, casual, sporty shoe that you can trudge around in on the weekends with ease. I love these Rothy's classic loafer in Leopard print

For a mix of sporty and classic, I often reach for my Rothy’s loafers. They are classic, comfortable, machine washable. I love the Cheetah print for some extra fun. You can’t beat having a shoe survive the washing machine that is comfortable to walk in and a chic shape/color.

A Cozy Pullover

Jennifer Connolly of A Well Styled Life shopping Everlane popup in Nordstrom Vancouver

I live in cashmere sweaters all fall and winter. I have many favorite brands but most of what I own is by Everlane. Their prices are excellent and they hold up beautifully with minimal pilling. I love classic shapes, preferably V-necks. They look great with a pair of jeans, trousers, or over a skirt. I know that cashmere care can throw some people off. I hand wash my cashmere sweaters with a mild soap, squeeze out the water, spin them in my washing machine, and lay them flat. Once they are dry, I iron them, and they look brand new! I check them over when ironing and remove any pills with my trusty sweater shaver (another wardrobe essential!)

Also – How To Wash Cashmere


What are some of your fall wardrobe essentials?

If you enjoyed this post, please share it to your Pinterest board.fashion blogger wearing wardrobe essentials


  1. Leggings, quilted vests, fleece tops are my go to because I live in the mountains So we dress down here. I have gone away from jeans unless they are lightweight & stretchy. Regular jeans are hot, stiff, thick & I do not thin they are very flattering on most people. Black cotton leggings are a great staple that you can dress up or down with different tops & shoes. Great for travel as well

  2. Great suggestions Jennifer even though I am not a long cardigan gal as prefer blazers or light Down filled jackets, for the Fall. Where I am temps are already in the mid 50’s so Autumn is definitely in the air.

  3. I have the worst time finding flat boots. I would take a trip home to Toronto where I have better luck (O how I miss The Bay!) but can’t do that this year. Years ago, you couldn’t even find boots in southern California (unless you were going skiing.) Now there are better selections online, but i want to try them on in the store rather than deal with endless returns through the mail. One of my biggest post-fire challenges has been replacing my shoes, and the boots are the worst..

  4. Judy Miller says:

    Hard for Florida gals to get excited by fall and winter😜
    I add long sweater to my summer clothes!

  5. I’m blessed living on the Coast because I can style around in Fall all the way up to Christmas some times so I get a lot of wear out of a Fall wardrobe. These are my five essentials too but I choose cotton sweaters so I can get more wear out of them in our climate.

  6. Since I retired to Maui 8 years ago one of the things I miss is jeans and boots!
    I always look forward to returning to the mainland for the holidays so that I can wear them! Cashmere sweaters are also in my closet for travel. So comfy and easy to pack.

  7. Christine Flaherty says:

    Hi Jennifer, your Frame Jeans reference takes you to Rothy??

  8. Good post Jennifer. I still love the look with the jeans, leopard belt, and eyelet shirt! I’m looking for a new pair of jeans also and I like Frame. When I clicked on the link for the Frame jeans you’ve been eyeing, it took me to Rothys. Which Frame jeans are you eying?

  9. Linda Henderson says:

    Jennifer, you look great. Love the looks.

  10. Love your blog. Hope you are well but wondering about your husband’s health. Have both of you in my prayers.

  11. Francesca B. says:

    I love Plaid shirts and leggings for Fall. I got a great deal on a Frank and Eileen plaid shirt at Nordstrom Rack and they have some nice ones from Treasure and Bond too. Love long cardigans too. Great post thank you Jennifer.

  12. MollIe M. says:

    Another great post Jennifer! I am also looking for a good pair of jeans. They are a great for Fall with a cozy sweater. This is my favourite time of the year and here in Ontario the trees are beginning to turn.

  13. I am a jeans sweater girl too! I love riding boots and booties. I have some high heeled boots that I’m thinking of giving away. Haven’t worn them in years! Love all the clothes you’ve shown here, look beautiful on you!

    1. @Rose: Depending upon the style and height of heel, sometimes they can be reduced. A shoemaker will be able to advise you. (I have three pairs of boots that I’ve had it done to.)

  14. Terri Reilly says:

    You look absolutely amazing – a Fall inspiration to us all!

    A quick suggestion about jeans that perhaps will be of interest to Susan R. I too have struggled to find just the right cut. Eddie Bauer has an interesting selection of choices. Their jeans are available in boyfriend, slightly curvy & curvy fits with skinny, straight, slim straight & bootcut leg styles; most are also available in petite, regular & tall. For those of us with ample hips & legs, the slightly curvy fit works…curvy offers a smaller waist with full legs & hips. Definitely worth a try – particularly if you can try them on in-store.

    1. Thanks for sharing that resource for us Terri! Have a great day

      1. Beverly Marshall says:

        I like the Hue jeans…easy to pull on, comfortable, wear well, good quality and around $45-$50 the last I checked. Also, there is no front button to pooch out or struggle with, so it creates a slimmer look with no obstruction. I highly recommend them!

  15. Linda Simpson says:

    Great minds think alike; I love pullover sweaters, cardigans, jeans, loafers, and boots in the Fall. I also have a cute pair of Converse sneakers to wear as well. Since I am retired, I don’t feel the need for heels and prefer my riding boots with jeggings. I do wear turtleneck sweaters but admit that I like the looks of v-necks better since I don’t have a long neck. Oh, and I cannot forget scarves as accessories to pull everything together.

  16. I must say how gorgeous you look in those cool colours. Looking forward to the last analysis. For fall, I am a jeans and sweater type with a variety of ankle booties, mostly flat. I like the longer cardigans as well, somehow they feel cosier. I have fingers crossed for a nice long fall season as I am not looking forward to the indoors for a long winter.

  17. I too am still looking for jeans that fit. I bought the dark wash Marilyn from NYDJ as you suggested. I was so excited- no whiskering, no fading no contrast stitching. However. The body of the jeans fit beautifully, but the legs on my sturdy thighs and calves fit like skinnies. And made all the horizontal lines of a too- tight fit. If I go up a size, the body is too loose. It’s just too marrow in the leg. I never wore skinnies because They weren’t (and aren’t) flattering showing my worst body part. I found the old j jill Tried and True straight leg on ebay. ( not dark was though) Of course j jill hasn’t made them in years. They made a cut called “Slim”… same problem of too tight legs. So the search goes on. Ideas anyone?
    Here in Connecticut we’re just starting to have cool mornings and nights. So grabbing a cardigan or a blazer ( looks better on me) over my mid wash jeans feels great.

    1. This year there are more “stove pipe” fit jeans around so you might have better luck. This style is often called wide leg, without a flare at the bottom.

  18. For as long as I remember, my fall favourites have been: a tweed blazer (or variation of), boots, leather gloves, jeans and cozy sweaters. This fall I’m determined to find a pair of jeans that I like – most likely straight leg in a dark wash. I just have to force myself to get into the stores to try some on LOL.

    1. A tweed blazer and suede boots just sound perfect for today.

  19. Another great post filled with inspiration and information! Thank you for sharing…

  20. I am a jeans and sweater girl in the fall and winter. Unfortunately, I am very sensitive to wool/cashmere and can not have it next to my skin at all. So I am always on the lookout for good quality cotton/cotton blend sweaters to wear. On my fall shopping list are a pair of straight leg jeans. I will still wear my skinnies most of the time, but I want something different on occasion. I pulled out a pair of wider legged flares I purchased from Talbots and am trying to decide if they work for me. After wearing skinnies for so long the wider leg is throwing me off style wise. It has turned cooler here in Indiana and I am savoring these temperatures while they last. Not looking forward to being cooped up indoors this winter.

      1. Claudette says:

        I am like you Michelle with anything wool. It is a little harder finding a nice looking sweater that stays in shape that is not wool.

Leave a Reply

Your email address will not be published. Required fields are marked *