How to Wear Denim Shorts at ANY Age and Look AMAZING! Everything You *Need* To Know

My Favorite Denim Shorts Over 40

One of the most common questions I get around the spring and summer is about whether or not women over 40 can wear denim shorts. Well, the short answer is…”yes, you absolutely can wear them.” I am definitely on Team Denim Shorts! And before you dismiss them for you because of any number of reasons/insecurities, please read through my essential styling tips below…for finding the perfect pair of jean shorts at any age! You might just change your mind. Plus, I’m sharing my all-time favorite pairs I wear on repeat each summer…

Find more do’s and don’ts for wearing shorts over 40 and how to feel confident wearing shorts here.

How To Find The Perfect Denim Shorts

Check The Rise

The shorts above have an 11” rise, so they’re very high-waisted, which can be quite flattering (when they don’t highlight the lower tummy – fit is key). 9” to 12” inches is considered high rise. I prefer high-waist shorts because they make my legs look longer!

Check The Inseam

I usually like to wear shorts with an inseam between 3” and 5”. 3 inches is pretty short, but if you are petite like me, you can get away with it. If you are taller (think 5’7″+) I would consider 5″ or longer.

Size Up

With denim shorts, it’s best to size up one size. You don’t want anything too tight in the waist creating a muffin top.

Think About Fit & Fabric

Give yourself some breathing room in the leg area (sizing up helps here). If the leg holes are a bit wider, it will make your thighs look smaller! Sometimes jean shorts have a sort of triangle shape where the legs bell out slightly. That’s the most flattering and slimming style. If the fit is too tight around the legs, they are not the right shorts, send them back and try again.

Bend Over

“Moon River. Hey doc, you ever serve time?” Anyone know that quote?? 😉 For REAL, when you put on the shorts, turn around in the mirror and bend over. I would also drop something and pick it up off the ground. If you can see your bum in that process (either at the top or bottom), they are not the right fit. This is likely due to both the rise and inseam.

Fingertip Test

How short is too short?? When in doubt, you can try the fingertip test. Put your arms down by your sides. If your shorts are WAY shorter than the end of your fingertips, you might want to opt for a longer inseam. If they are close or even below the fingertips, you are good! Longer arms? Be sure to add that into your calculation here. And, remember this is just a guideline. You do not have to adhere to this rule.

Find my favorite pairs of denim shorts below…

#1 | Moussy Vintage Jean Shorts

All-time favorite pair…(drumroll please) Moussy Vintage jean shorts! (I also LOVE their jeans.) I’ve had this pair for about four years and…I love them! They’re comfortable but the denim is stiff enough to make you feel secure. The length (3” inseam) and high rise (11”) are great. And I love the distressing and raw hem. They also have plenty of room around the leg so that they have that looser-looking fit! Moussy has different styles of denim shorts but I’m wearing the Packard style…I haven’t tried the Chester, Wheatfield, or Mililana styles yet. (Sizing note: if you are long from waist to crotch, this is NOT the right style or pair for you.)

Shop more by Moussy Vintage shorts and jeans here.

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#2 | R13 Crossover Shorts

I packed these shorts for a recent trip to CA and they did not disappoint! I love the cool crisscross front, 3.5” inseam, 15” front rise, and roomy legs for the ultimate flattering fit. The baggy jean trend is definitely transitioning over to denim shorts, and I’m here for it. They’re a little pricey but I’ll share more affordable options in the following looks as well. These shorts do run a bit big so I sized down one size, and you can see they still have that just right, oversized fit. Since the jeans have some distressing and more of an overall edgy vibe, I paired them with a super feminine ruffled top by Farm Rio and a floral beaded bag by Staud to create some contrast. If you already have your basic pair of denim shorts, these would be a fun new twist to add to your wardrobe.

If you’re on the hunt for the perfect white top to pair with your denim shorts including the one pictured above, make sure you check out this post next!

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#3 | Pistola Cutoff Denim Shorts

Next up are these distressed jean shorts by Pistola that have the perfect wash for spring/summer. These have about a 3” inseam, which is a great length for me at 5’4”. I love the light distressing at the hem and flattering high-rise. The legs are a little roomier so they’re really quite flattering. They run true to size and have a relaxed fit, but these have no stretch so that’s something to keep in mind. They’re 100% cotton and very soft and lightweight. I styled them here with a Bronx & Banco blazer, cropped white button-down, and some neutral wedges, but these will be those shorts you throw on all summer with a t-shirt and sneakers or floral print top and sandals. If you’re looking for a more budget-friendly pair of denim shorts, these are affordable without compromising quality.

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#4 | Pistola White Cutoff Denim Shorts

SO nice, I bought them twice! These are the same Pistola denim shorts from #3, but this time in white. Unlike the blue denim version, these do have a little bit of stretch to them. They have all the same flattering features like the high waist and roominess in the leg as well as the same cool distressing. If your white denim shorts need some updating, I highly recommend this pair. I styled them here with a lightweight open-knit pullover by Velvet. I love mixing white, ivory, and cream tones for more of a monochromatic look. This was such a perfect outfit to wear in CA during my last trip…beachy, effortless, chic, and comfortable!

Keep scrolling for a few more of my favorite denim shorts from previous seasons…

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#5 | Agolde Jean Shorts

These were my go-to denim shorts before I found the Moussy Vintage shorts…but don’t get me wrong, I definitely still wear these shorts each summer too! This brand, Agolde, is a line by the same designer as 7 For All Mankind and Citizens of Humanity…both amazing denim brands, so they definitely know what they’re doing with denim! Agolde is known for its trendy jeans and amazing denim shorts. These shorts give me a 90s vibe I love, but with a twist. I love the minimal distressing, raw hem, and high waist.

These are not your average high waist shorts…they have almost a 12” rise! So you feel very secure and tucked in. The inseam is 3.25” so they’re not too short and completely cover your bum. The shorts I’m wearing are the Dee Shorts but unfortunately, the exact wash is sold out since I bought these so long ago! But this pair is very similar.

More AGOLDE shorts here.

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#6 | Agolde Uncut Hem Jean Shorts

After wearing my Agolde Dee shorts and Moussy Packard shorts for years, I decided it was time to try a new pair of denim shorts last year…the Agolde Parker Long Loose Vintage Shorts. You probably noticed something a little different about these shorts…they don’t have a raw hem! I love that this version of the Parker shorts has an uncut hem that makes them feel a little more polished than a raw hem. They have an 11” rise and 4” inseam so you still feel secure in the tummy area and covered in the bum area. The whiskering and fading are minimal and there’s no distressing…something I know many of you prefer! I’m wearing the wash “Occurrence” that’s the perfect medium wash. But they also come a few other washes here and there is a version of the Parker short that does have distressing here if you are interested.

#7) Agolde White Jean Shorts

Here is another pair of white denim shorts that have a longer inseam than the Pistola white denim shorts I shared in #4. In the photo above, I’m wearing the Parker Long shorts in white (called “Panna Cotta”). These have an 11” rise, an almost 5” inseam, and they’re not see-through at all…a must if you’re going to wear white shorts or jeans! The fabric in the pockets is also super lightweight so you don’t get that weird bulking and bunching around your hips.

Shop more denim shorts here.

Have you found a pair of denim shorts you love?? Don’t keep that to yourself! Please share in the comments below!

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