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Feel Your MOST Confident Wearing Shorts Over 40 With These 8 Simple Style Tips

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How To Wear Shorts Over 40

We’re talking about one of the most controversial fashion items for women over 40…shorts! I get tons of questions around this time of year about how to wear shorts over 40, what shorts are best for women over 40, how to style shorts…the list goes on and on. There may be voices in your head saying you can’t wear those shorts. But there’s another voice saying…IT’S HOT, I want to wear shorts, and I want to look good doing it! But how?! Don’t worry, if you’re wondering how to style your shorts this summer while still looking chic and sophisticated, this post has all of my best tips! Plus, I’m sharing some of my new favorite shorts for the summer…


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SHORTS | BLOUSE | HAT | FOR LESS | SIMILAR SANDALS

Tip #1) Try A Longer Inseam

If we’re trying to look sophisticated, we don’t want to wear tiny short shorts like our teenage daughters, right?! So, when you’re shorts shopping, look for a longer inseam! Between a 4–5-inch inseam length is ideal. But if you’re petite (under 5’4”), you can get away with a 3–5-inch inseam length. Another fool-proof way to check the length of your shorts is the fingertip test. Hold your arms by your sides and if your fingertips are at or below the bottom of the shorts, that’s a good length. Another popular option is Bermuda shorts. But they can be tricky because they can cut you off and make you look shorter. Look for a pair of Bermuda shorts with a 7-9-inch inseam and make sure you style them in a chic way. A lightweight, longline blazer can look very chic and stylish with any pair of shorts, but especially cool with Bermuda shorts.

Another major tip for styling your shorts is to make sure you pair them with a top that’s more refined and elevated. The problem with wearing shorts is that they can sometimes look too casual. So, elevating the look with those more interesting, chic pieces can help. Instead of a plain tee, opt for a tee with an interesting design detail like puff sleeves, ruching, ruffles, a print, or a strategically placed cutout.

The little details are what make the biggest impact.

 

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SHORTS | TOP | WEDGES | NECKLACE

Tip #2) Try Shorts with A Wider Leg

Avoid shorts that are super tight. Instead go for shorts that have a wider leg. The tighter the shorts are around the leg, the bigger your legs will look. If you give yourself some room in the leg, your legs will actually look smaller. Look for a pair of flare or A-line silhouette shorts. The Jonathan Simkhai shorts I’m wearing above are the perfect example. You can see the wider, A-line silhouette actually makes my legs look slimmer and longer. The A-line shape can also help mask or minimize your hips, butt, and thighs if that’s your problem area. I styled the shorts with my favorite Rails button down and a new pair of woven wedge sandals by Veronica Beard that are perfect for summer.

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SHORTS | BLAZER (SOLD OUT) | SIMILAR CAMI | SIMILAR HEELS

Tip #3) Buy High-Rise

Choosing a higher rise will make your legs look longer. This is true for all bottoms…pants, jeans, skirts, etc. But a higher rise also helps create a waist. If you really want to accentuate the waist, wear something like the Alice + Olivia set I’m wearing above. The cropped tank hits right at the top of the shorts, which helps show off the waistline, and the blazer slims the sides even more. You could also add a belt to help create waist definition. So what rise is best?? The ideal rise for everyone is different. Generally, anything above 9 inches is considered high rise, but I’d look for something in the 10-inch zone.

By the way, I know shorts shopping can be really tricky. My go-to brands to look at when I’m shopping for shorts are Alice + Olivia, A.L.C., Ulla Johnson, Frame, Marissa Webb, and Amanda Uprichard. J. Crew is also very clear on rise and inseam length and has a lot of options.

If you’re looking specifically for denim shorts, make sure you check out this post!

 

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SHORTS | TOP | SANDALS (SOLD OUT IN BROWN) | SIMILAR IN BROWN

Tip #4) Size Up

Do NOT get caught up in the vanity sizing. Just because you’ve been a size 6, does not mean you’re going to be a size 6 in every piece of clothing and every pair of shorts you try on. I’ve been ordering larger sizes in my tops, jeans, and shorts lately because right now, I’m really just enjoying a roomier fit. I even ordered my favorite Rails top (above) in a medium for a more oversized fit! Sizing up in your shorts gives you a little extra wiggle room and will actually make them look more flattering on your stomach and legs, polished, and elegant.

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SHORTS | SIMILAR TOP | HEELS | NECKLACE | SUNGLASSES

Tip #5) Choose Shoes Strategically

Since you’re showing a lot of leg, your shoes are really important. I would go with a pair of sandals or heels that match your skin tone. It doesn’t have to be perfect, but in the general zone. Another tip: If you add heels or wedges, it gives you more height! I’m wearing these cool pinstripe Marissa Webb shorts with a pleat sleeve tee by See by Chloe. The tee is sold out but I linked a more affordable option I own and love. On my feet, I went with some tan See by Chloe platform heels. You can see that the color doesn’t perfectly match my skin tone, but it’s in the same zone and therefore helps elongate my legs.

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SHORTS | FOR LESS | TEE | BELT | BAG | SIMILAR SANDALS

Tip #6) One Skin Rule

I’ve talked about the One Skin Rule many times. And I know that during the summer, it’s tempting to throw on a tank top with your favorite shorts. But since you’re showing so much skin on your legs, it’s best to wear a top with short, 3/4, or long sleeves. I did live in Texas for 8 years so I know how hot it can get. But wearing longer sleeves in natural, breathable fabrics (like cotton or linen) will still keep you cool and looking sophisticated and elegant. Also, don’t forget those elevated style details I mentioned earlier…puff sleeves, ruching, wrap front, texture, etc. My secret weapon when it comes to cool t-shirts is the brand Nation LTD…the fit is great, the fabric is high quality, and they are what I like to call t-shirts in disguise because they look like blouses and can really elevate a look!

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SIMILAR SHORTS | ANOTHER OPTION | BLAZER | SIMILAR CAMI | HEELS | NECKLACE

Tip #7) Body Care

Last but certainly not least…take care of your legs! If you’re going to get them out, make sure you shine them up! What I like to do is take some lotion and mix it with this Charlotte Tilbury Super Model Glow and rub that into my legs. If you are going the tanning route, make sure you proceed with caution so that you don’t end up staining any of your clothes, sheets, etc. We did an entire post on self-tanners for summer here if you’re interested. Adding the color just makes my legs look a little better and makes me feel good! You’ll walk out the door feeling a little more confident. Another thing that will help make your legs look darker is adding a pop of color. In the look above, I’m wearing a pair of super flattering paper bag shorts with a simple cami and one of my favorite blazers by Cinq a Sept. I love the pop of color and this mint green is perfect for summer!

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Tip #8) Tie the Look Together

Now you have the perfect pair of shorts, a chic elevated top, strategically selected shoes, and summer-ready legs…what else do you need?? To kick your shorts outfit up a notch, make sure you complete the look with accessories that can pull it all together. It could be a hat, belt, cool pair of shoes, chic sunglasses, or some statement jewelry. I’m wearing a cool, chunky gold necklace with the look above and it just adds a little extra oomph!

For more of the do’s and don’ts of wearing shorts over 40, make sure you watch this video. And to see more women over 40 wearing shorts, this post is a must-read!

What other questions do you have about wearing shorts? We’re happy to answer them! Please leave a comment below.

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