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.

My Favorite Denim Shorts Over 40

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…

Moussy Vintage Jean Shorts | Favorite Denim Shorts Over 40

#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.

R13 Crossover ShortsR13 Crossover Shorts review

#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!

Pistola Cutoff Denim Shorts

Pistola Cutoff Denim Shorts outfitPistola Cutoff Denim Shorts for women

#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.

Pistola White Cutoff Denim Shorts

White Cutoff Denim Shorts with mesh topCutoff Denim Shorts with mesh top

#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…

Agolde Jean Shorts, how to wear shorts over 40how to wear denim shorts over 40

#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.

Agolde Uncut Hem Jean Shorts pink aje blouse, agolde parker long vintage shorts

how to wear shorts over 40, Favorite denim shorts over 40

age appropriate denim shorts, Favorite Denim Shorts Over 40, how to wear shorts over 40

#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.

button down rails chambray shirt, white agolde jean shorts

#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!

Be sure to subscribe to my newsletter to receive some incredible style resources. We just released a Spring Occasion Lookbook with 40+ outfits and it’s a MUST see. You can access it here.

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Join the Conversation

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

  1. Will you please recommend some great denim shorts with 7” inseam. They are hard to find and when I do they fit tight around the leg. I like a bit of a flair. Thank you for all your detailed content.

    1. Hi Stephanie! Here’s some great options for you to look at… The 7″ inseam is tough to find so I included a couple of great options that are just a touch shorter as well… Thanks for reading! ~Team Busbee
      AG 7″ Inseam |
      AG 7″ Inseam w/ distressing |
      Jen7 6 1/2″ Inseam |
      Levi’s 6″ Inseam |

  2. Hi Erin! I’m a tall curvy women over 50 and I don’t really like to show much leg, so I was wondering if would 7” or 9” would ok? Do you have any brand suggestions? Thank you for always having such great content. Love everything you put in your newsletters!

    1. Hi Michelle! Agolde has some great options in longer lengths including a 9.5″ inseam: These have a longer 5.5″ inseam but the legs are a looser fit and have a fun crisscross waist: These also have a longer inseam (8.5″) but we have not tried them: Hope this helps! Please let us know if we can help you find something else. Thanks so much for stopping by! ~Team Busbee

  3. This is such a great post, because it shows there doesn’t need to be any “age limit” on denim shorts; they can be youthful and cool, without ever going into that dreaded “I-look-like-a-teenager” place! (And here in SoCal, they’re absolutely a must-have staple.)

    My trick? If you’ve recently (or not-so-recently, depending on how long you keep your clothes, lol) lost a little weight and gone down a size or two, choose a previously-favorite pair you no longer wear (in that one-larger size), grab a pair of fabric shears, and create your own cut-offs! (Always remember to measure and mark the length you want, first, though–that old “measure twice, cut once” came about for a good reason!) It’s completely eco-conscious, giving a whole new life to something you’d otherwise be giving away or consigning… and costs you absolutely nothing. To me, that’s a win-win!

  4. Brilliant post, Erin. Denim shorts can be tricky but these tips are fabulous and shows they aren’t “off limits” if you pay attention to how to wear them in a flattering way. Thank you!

  5. Love it! I am having a jean transformation! High rise for me now… I got “Good American” destrcutive faded shorts but love what you have. It takes a while to get used to it. It’s so hot here that I will wear that with a fancy top to a restaurant. thanks for all you do! It’s difficult to stay caught up with all you do!

  6. I love your chanel, and your news letter! Its one of the few emails i ACTUALLY open! Love Seeing colorado. Makes me want to move from California. Keep doing what your doing, you make a big DIFFERENCE in womens lives. May God CONTINUE to bless you.

    1. Aw, thanks, Irene!! I love the newsletter too. I love sharing in that way. California is pretty amazing too! Come visit CO!! xoxo

  7. Erin, I’Ve been RECEIVING your emails foR quite a while now. I happenend upon your site when i was searching for age appropriate/non-frumpy clothes. Now that I just turned 60, i am not ready to join the baggy capri look. I am a high school physical education teacher that wears gym clothes to work everyday. I’ve struggled over the years in my professIon of Trying to dress like a girl, over dressing masculine, as some other colleagues in my profession do. My husband Tells me there is no way i Can look like a boy(so sweet!) . I enjoy Wearing “normal clothes” on the weekends, for teacher meetings, Etc. i identify with your struggles of trying to stay fit while working full time. I am about The same size as you, but struggle with the saggy skin of 30+ years of southern californiA sun. (Back in the day, sunscreen was not emphasized) my work shorts have gotten longer, as have my sleeves;) i want you to know, i really enjoy your Seeming AUTHENTICITY and humbleness. Your Shared struggles of feeling down and reaching out is so endearing. I also truly enjoy your tips on trends and Style. Some of the styles you wear, i never would have considered, but you alWays manage to make it look so cute With style and not “stuffy.” Even lOw cut items, look cute and not trashy(i hate that word, but for lack of a better one) 🙂 i also enjoy your travEl tips, as my husband and i travel light to Europe for a few weeks every summer. i want to encourage you to continue with your clasS, style and humbleness. You are a True gem. Thank you for giving me the opportunity to write my first ever Note to someone in the media. 🙂 may God bless you.

  8. I especially like the belt and the bracelet. Can you list those also??? Thanks Erin. I’ve gone for a lot of your recs these past few years.

  9. Hey erin! Cant wait to order those shorts! Question – with such a high rise, how do shorter ladies woth bogger boobs make that outfit work?

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