Best Denim Shorts for the 40ish crowd

Denim shorts are by far the most worn thing in my closet in the warmer months. They’re comfortable to wear all day, go with any top, and look cute with all sorts of shoes. If I had to guess, I’d say I wear them 5 times a week at least.

But, as an almost 40 year old, finding denim shorts that are not too short or too tight is challenging. I’m not comfortable wearing short-shorts anymore, and SO many of the jean short options on the market are super short and tight (and look like they’re better for a 15 year old than a someone in their late-thirties). So over the past couple of years, I’ve made it my mission to find denim shorts that are cute AND appropriate for my stage of life.

Luckily, I’ve had a lot of success this summer. I bought and reviewed a handful of different styles from a few different brands, and in today’s post I’m sharing my favorite finds. If you’re like me and you struggle to find jean shorts that you truly love, keep reading. This is for you!

How to find the best denim shorts

Try on a lot. Seriously. I had to try lots of different styles at various price points before finding a pair that felt totally comfortable on me, but it was worth the search. Since jean shorts are a summertime staple, you want to LOVE the pair you’ll be wearing everyday. I did the same thing when it came to white jeans. I tried 15 pairs of white jeans before finding my favorites — it just takes time!

What type of jean shorts are in style 2023?

I’ve been SO thankful to see so many relaxed, high rise options this year. The super tight, cuffed look is not quite as popular as it used to be, and I’m excited about that. I like for my shorts to have room through the thighs, and thankfully, it seems clothing designers do too (this year, at least)!

What is the most flattering length for jean shorts?

This boils down to what you feel best in, but in general, a high waisted pair with a mid-length that doesn’t show your booty is a good, flattering choice.

Is it better to size up or down in denim shorts?

This will vary from brand to brand, but I actually found that I wore my true size in every pair (except one – details below). If I am in-between sizes in denim, I always go up in size for comfort and so that I don’t feel like I’m forcing myself into them.

Okay, ready to see what I’m loving this summer?

Best Denim Shorts

Agolde Parker Long Shorts

My #1 pick is the Parker style from Agolde in the longer length. I bought my first pair last year which was a raw-hem, distressed style, and ordered a second pair this year with a finished hem in a darker wash (which is one inch shorter than the distressed pair). Both are super similar, the only difference being the distressing and extra inch in the inseam for the raw-hem style.

The main selling point in this pair of shorts is that they are a non-stretch denim. This means that instead of feeling like stretchy leggings (I feel like so many pairs of jeans feel like this now!), they have a rigid feel that loosens as your wear them throughout the day. I tend to keep them out of the wash as much as I can since I love how much they loosen out with a few wears, and once you wash and dry them, they tighten back up. I wear my true size 25 in these.

These are a high rise style with a relaxed fit so they’re loose throughout the thigh, which is one of the reasons they’re so popular. While I typically hate a button fly, these don’t bother me. The longer, 4″ inseam is PERFECT for extra booty coverage that doesn’t look frumpy.

The only downside is that these are the priciest pair of denim shorts I’ve ever owned. At $148 they are definitely not an affordable pick, but after having multiple other pairs, I still like these best. They are well worth the splurge since they are a classic style that you can wear for years.

Here are a few snaps in the distressed pair:

I ended up ordering a pair of denim shorts from Banana Public Factory in hopes that they’d be great dupes for the Agolde pair and they shrunk a TON after washing them, so alas, I have not found a proper dupe yet!

J.Crew High-rise Denim Short in Delery Wash

Next up on the list (and my second favorite pair of jean shorts), is this light wash pair from J.Crew. There are so many things I love about this pair, but my favorite thing is the wash. In the summer, I always reach for lighter denim. It feels so fun and casual, and since I already had the darker washed pair above, this was my next purchase.

Like the Agolde pair above, these have a 4″ inseam and are mom-approved. They’re a little stretchier than the Agolde pair, so if you prefer stretchy denim, this is your pair. They’re comfortable all day and have a flattering high rise waist. While they aren’t quite as relaxed through the leg as the Agolde pair, they aren’t tight. These fit true to size — I wear a size 25. If you are between sizes, I would size up.

Best part? The price tag. These are listed for $89 at full-price but have been discounted to $54 for the majority of the summer.

Madewell Relaxed Denim Shorts

Next up, the Relaxed Denim Shorts from Madewell. This is a SUPER popular pair of jean shorts because of Madewell’s reputation for good denim. They have a similar fit to the J.Crew pair above but with no stretch (my preference!). They’re a relaxed fit, which gives you a nice amount of space through the thigh. The length is also mom-approved (5″). This Relaxed style comes in a handful of washes and variations (including an even longer mid-length) from Madewell.

I own the White Tile wash and the Mid-Length Denim Shorts in Kimbrough Wash, which has a side slit.

In years past, I felt like the sizing for this style was wildly inconsistent, but this year, my true size 25 fits well. They’re looser than other size 25 pairs I have, but I believe that’s because of the relaxed nature of the fit, versus the size.

Madewell Patch-Pocket Denim Shorts in Earlwood Wash

This pair of jean shorts aren’t necessarily a classic denim short style, but if you’re looking for a second pair of jean shorts that have a more tailored look, this is the pair for you. I LOVE them. The Patch-Pocket Denim Shorts in Earlwood Wash has an a-line style that’s incredibly flattering. Since the waist is fitted, it’s slimming in the right places and then the legs are wide in the right places too. If you hate when jean shorts feel stuck to your shorts, you will love this pair.

These run SMALL! I got a size 25 and will need to go up to a 26.

Madewell Baggy Jean Shorts

For a much longer denim short option, I ordered this new style from Madewell. They’re much more of a Bermuda length, which seems to be coming back this summer. I love how Madewell has made these feel fun and modern with the raw hem while still maintaining the conservative length.

This style comes in a few different variations and washes, so the details I’m sharing below may not be correct for all of the Baggy Jean Shorts that Madewell carries. I got my true size 25.

Madewell Perfect Jean Shorts

If you like a simple, stretchy jean short, then this is the pair for you. While these were my least favorite of all of the shorts above, they’re still a great option for anyone looking for superior comfort. The Perfect Jean Shorts are also a high rise style, but have a much more fitted look. They’re tighter through the leg, which is not my preference, but they have a great long inseam that I do like. Like most Madewell jean shorts, there are multiple lengths and wash variations for the Perfect Jean Shorts, so these are just my thoughts on this specific pair

I got my true size 25 and I’d say they fit true to size. The lighter wash is such a nice summer option.

I hope this post helps you find the PERFECT pair of denim shorts for the summer. I know how hard it is to find the right pair, but once you do, you’ll be happy all summer long.

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