6 Ways to Wear Long Shorts for Fall (aka Bermuda Shorts)

Midlife women wearing Bermuda shorts, white tee and tan blazer

Right about now, my Instagram feed switches from summer dresses & shorts to sweaters & boots. But here on the West Coast, we are still firmly rooted in summer even with the Fall Equinox right around the corner. The weather here is hot! In fact, some of our hottest days are ahead. So it is no surprise we want to rock the shorts well into fall.

Long short (aka Bermuda shorts) are perfect for the transition to fall. Fashion girls are wearing their long shorts, baggy, and pleated. But as a woman of a certain age, I don’t want to add any additional bulk around my middle. I prefer the streamlined look of the Vince Bermuda Shorts. The style is more tailored with slim legs providing a more polished look to your outfit.

If you’re not quite sure about spending so much on shorts, the Liverpool Lacie Bermuda Shorts are under $60 and a great alternative. I often try a trend with a less expensive option then upgrade to the more luxurious pair when I know I will wear. I did this with my Stuart Weitzman Lowland Boots. First, I purchased the Jeffrey Cambell dupe to make sure I would wear them enough, and then I invested in the SW, which will last a lifetime.

Bermuda Shorts are a fabulous alternative to trousers and skirts for fall. Read on for six ways to style long shorts this fall.

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Styling Bermuda Shorts for Fall

Outfit #1: Bermuda Shorts + White Tank + Tan Blazer

This outfit is an easy take on a short suit. Instead of buying a suit, use separates to build one. I added a the Long & Lean Linen Fit Blazer from Banana Republic. Generally, I size up in blazers for a bit more room in the shoulders. Apparently, I am not Long & Lean because I sized up two sizes for a good fit.  If you want a tailored fit size up only one size.

The tank top is from AMO, which I discovered during my hunt for The Perfect Non-See-Through White Tank. Yes, $79 for a tank top seems extravagant, but I reach for this tank all the time. It works as a layering piece or alone. I love it so much. I went back and bought the black.

Women wearing bermuda shorts blazer and sandals

Outfit #2: Bermuda Shorts + Hoodie + Denim Jacket + High Tops

Bermuda shorts give you the option to wear casually or dressed up. My lifestyle is pretty casual. The key for fall is to layer. Long before our days grow cold, our mornings start cool. It isn’t uncommon to have a 15 to 20-degree swing in temperature in a single day. During fall, I never leave home without a jacket or sweatshirt.

Both my denim jacket and sweatshirt are lightweight. Layering gives me warmth in the morning but then I can remove layers as needed throughout the day.

Midlife women wearing bermuda shorts, Everlane sweatshirt, L'Agence denim jacket and Golden Goose Sneakers Midlife women wearing bermuda shorts, Everlane sweatshirt, L'Agence denim jacket and Golden Goose Sneakers

Outfit #3: Bermuda Shorts + Interesting Blouse + Kitten Heels

There are a couple of reasons that I love this top so much. 1. It has interesting detail with the grommet and knot. 2. It is perfect for hiding the 50-something tummy. My shirt is no longer available, but the rag & bone Victor Silk blouse is similar and on sale. I have the Victor Silk blouse in the sleeveless version. I wear it all the time.

For the most part, I am a flat shoes girl, but when kitten heels made a comeback, I decided the mini heel was just my speed. I’m wearing the Stuart Weitzman Estela kitten heel. They look great with everything from these shorts to jeans.

Over 50 women wearing rag & bone top, Bermuda shorts and kitten heels.

The top below is Vince. I buy another Vince top every year at the Nordstrom Anniversary Sale. This year I bought this Vince Top in the beautiful champagne color. These tops are incredibly versatile. Silk & cotton are my two favorite fabrics for hot weather.

Midlife women wearing Vince top, Vince Bermuda shorts, red sandals.

Here is another take on the same outfit—this time with denim Bermuda shorts. Mine are the Amelia Cuff Bermuda Shorts by Hudson. I prefer the Amelia shorts because they have a flat pocket in the back. The Hudson button flap pocket doesn’t work well with breezy tops. It adds bulk that isn’t needed.

The look has a casual yet dressy vibe perfect for lunch with your girlfriends. BTW – I had my first lunch out since February with my girlfriends. It was glorious to catch up with them. The world isn’t the same, and I was stressed, but it was such a treat to spend time with such fabulous women. I won’t take their company for granted ever again.

Midlife women wearing Bermuda shorts with a statement top.

Statement Top Picks

Outfit #4: Bermuda Shorts + Silk Camisole + Utility Jacket

If you have been following along for any time at all, you know I love my utility jackets. They are the perfect topper for fall when the weather is still warm, but your tan has started to fade, and your arms are looking a little pasty. That is me about 90% of the year. #palegirlproblems for sure.

I have finally admitted that I am addicted to utility jackets. Every time I see a new one, I want it. They are just so versatile. This jacket is the Rails Collins Military Jacket. I picked this one up at Nordstrom Rack a few months back. There are a few there now but limited supply. It was also available at Nordstrom. I had to restrain myself from buying it in black during the Anniversary Sale. I already have three: this one, a camo version, and olive green. I told you I had an addiction, right? Even in writing this post, I am still considering the black. It is honestly the perfect warm-weather jacket.

Another item I have recently started collecting is silk camisoles. A good silk camisole will last forever. They are great for layering under a sweater in winter, wearing alone in summer, or wearing under a blazer for work. I prefer silk to all other synthetic material because it breathes and keeps you both warm and cool as needed for the season. Plus, they are available at all price points. The one I am wearing is Frame. I always pick up my silk camisoles on sale.

Midlife women wearing Bermuda shorts, snake print camisole, Rails blue military jacket and sandals.

Midlife women wearing snake print camisole with Rails Blue jacket.

Outfit #5: Bermuda Shorts + Graphic Tee + Denim Jacket + Sneakers

I can’t go on without commenting on my hair. It is all over the place in this post. The reason for that is, I come up with post ideas in several ways, but one is by looking at trends in my own Instagram feed. So these photos cover several months, including some time during the C19 quarantine, which explains the wildness of my hair. Well, my hair is always kinda wild except for the first two weeks after a haircut.

Ok! Back to long shorts, now. There isn’t an item of clothing you can’t wear with a graphic tee. Maybe a ball gown, but I bet you someone rocks it at an award show someday a la Sharon Stone in the J.Crew button-up shirt and full taffeta skirt. So, of course, a graphic tee looks great with Bermuda shorts. Keep the look casual with your favorite kicks. Add a denim jacket for the cooler fall days. Outfit perfection!

Midlife women wearing Bermuda shorts, graphic tee, L'Agence denim jacket and Golden Goose Sneakers Midlife women wearing Bermuda shorts, graphic tee and Golden Goose sneakers

Outfit #6: Bermuda Shorts + Pajama Top + Booties

Bermuda shorts with booties isn’t for everyone. I can hear my height-challenged friends screaming, “no way!” but if done right, it can be a fun and fashionable look.  The trick is picking the right booties for your height. I have long legs so I can get away with booties that end above the ankle bone, but if I were shorter, I would stick with booties that end just below the ankle bone.

Booties and Bermuda shorts shorten the look of your leg, and I get that can be unappealing. However, I think the look is fashion-forward and adds a new dimension to a look. Fashion girls wear tall boots with baggy Bermuda shorts, and I love the idea. Since I am skipping the baggy short trend, I will stick with booties with my tailored long shorts.

Over 50 women wearing Maje pajama top, bermuda shorts and white booties.

Long shorts are a fun way to transition into fall. The look is on-trend and quite practical for the Indian summer, which hits us as fall begins. Long shorts add a little more coverage than other short lengths but still keep you cool. The right pair can be worn casually or at the office. Do you all go to an office right now? My daughter calls them “mom short,” but I told her that is because moms are always practical. These shorts are entirely practical and super fashionable.

I would love it if you followed me on Instagram for my everyday outfits or on Pinterest for my fashion inspiration. StyleDahlia is a fashion and lifestyle website with a modern take on midlife. We hope to inspire you to step out of your comfort zone, try new things, and live your life in full bloom.

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StyleDahlia is a fashion and lifestyle blog with a modern take on midlife. We celebrate the beauty in everything whether it be fashion, travel, or home. StyleDahlia offers and honest take on aging, fashion and everyday. Our hope is to inspire you to see beauty in the little things, step out of your comfort zone, try new things, and live your life in full bloom.

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