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 subsiding in many places. It was definitely beginning to feel like fall on our drive back from Vancouver 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.

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

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.



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

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!

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.

Rothy's classic loafer in Leopard print

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 Robert Zur  ‘Petra’ Driving Shoes because they’re comfortable and come in a million colors. The woven top portion makes them extra cozy.

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

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?

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