How to Style a Chic and Casual Fall 2021 Outfit High Low

It’s time to pull together the perfect casual fall outfit for 2021 that’s ideal for women over 40, or any age for that matter. It is casual and sophisticated yet appropriate wherever you go. This look may seem familiar because it is reminiscent of the 90s, however it has a few twists that are totally new and on trend for fall 2021.

A Go-Anywhere Casual Fall Outfit

You may still have a glen plaid jacket from the 90s, but if not, designers like Saint Laurent, Micheal Kors, Altuzarra, Akris and others updated them for fall 2021. In the 90s we may have worn our black denim jeans with a black top under this jacket, but another runway trend that works is head-to-toe denim. A blue denim base is a fresh way to brighten and soften up a structured plaid jacket.

The 90s Fashion Trend

Do you remember the chunky heeled loafers of the 90s? They are back in style, too. Only now you can find interesting details like studs, buckles, lug soles and other variations on the trend that makes them less boring. Add a pop of red with a crossbody bag to complete this stylish yet practical ensemble. Here is how to style this casual fall outfit high or low.


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Style It High Low

You can go all high-end designer, or get the same look with low-price pieces that will cost you a lot less. Better yet, mix them up for a high-low styled outfit and get the best of both worlds.

The Glen Plaid Jacket for Fall

A perfect fall topper is a lightweight wool check blazer. This is a classic plaid that works well with denim as swell as solid black or camel pants and skirts. It pairs well with paisley and floral print blouses the same way a colorful pattern tie works for a man’s suit jacket. You can wear it styled more fitted like this impeccably tailored Saint Laurent Prince of Wales checked wool blazer for $2,990. Or go slightly more oversized with this Dorset Blazer in Bowne Plaid from Madewell for $175. I had to do a little math and found out you can get 17 Madewell blazers for the price of one Saint Lauren jacket! Hope that helps you decide.

High Waist Straight Jeans

I’ve been preaching the high waist straight or looser leg jeans for a while now. That’s because I think they are comfortable, figure-flattering and more forgiving than skinny jeans. These AGOLDE 90’s Pinch Waist High Rise Straight Fit Jeans are a best seller for $188. But you can save on these denim Banana Republic High-Rise Straight Organic Jean for $109. They have a bit of stretch, too. Order both styles in a few sizes and see which ones fit you best. When it comes to a great-fitting pair of jeans you will always get your money’s worth no matter how much you spend since you will wear them every other day! We call that Cost Per Wear.

The Denim Shirt

A chambray shirt is a wardrobe essential and is super versatile. It looks sharp with black denim, grey wool, floral printed skirts, plaids and with leather jackets. It also works with denim jeans. This head-to-to denim trend was evident on the fall 2021 runways. It gives you a jumpsuit-like base of denim to style under any jacket or coat. It’s best to look for a shirt in the same shade of blue denim as your jeans, but you can also go a shade off. This Frank & Eileen Cotton Chambray Button-Up Shirt is super luxurious for $268. But you can also pick up a Gap Denim Western Shirt (on sale too) for only $41.99.

The Black Loafer

Give your feet a break and slip on some loafers! These cool Valentino Garavani Roman Stud Loafer are $890 and (as shoe collector) I think they are worth the price. Get them before they sell out! The strategically-placed oversize gold studs make a nerdy pair of loafers look so cool! Or you can get a similar shaped shoe and a lot less attention with these Sarto by Franco Sarto Eda Loafers with little buckle embellishments for only $99!

The Dark Red Crossbody

Add a pop of fall color with a crossbody bag that is lightweight and still will hold all your essentials. It is Fire Whirl red, a color listed in the Pantone New York Fashion Week Autumn/Winter 2021/2022 trend report. This Saint Laurent Solferino medium leather shoulder bag is gorgeous and quite collectible for $2,800. Or go with a classic Coach Kip Leather Crossbody Bag for only $225 in the same shade for fall 2021.


Saint Laurent Prince of Wales Checked Wool Blazer, $2,990

AGOLDE 90’s Pinch Waist High Rise Straight Fit Jeans, $188

Frank & Eileen Cotton Chambray Button-Up Shirt, $268

Valentino Garavani Roman Stud Loafer, $890

Saint Laurent Solferino Medium Leather Shoulder Bag, $2,800

Total High Outfit Price: $7,136


Madewell Dorset Blazer in Bowne Plaid, $175

Banana Republic High-Rise Straight Organic Jean, $109

Gap Denim Western Shirt, $41.99

Sarto by Franco Sarto Eda Loafer, $99

Coach Kip Leather Crossbody Bag, $225

Total Low Outfit Price: $649.99

How would you wear this outfit? Would you style it high, low, or high-low?


Carol Calacci

You may also like to read How to Style A Comfy and Chic Travel Outfit High and Low and How To Style A Chic Beach Outfit High Low.

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Disclosure: Pants were provided for review and the opinions are my own.

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