Denim Short Guide 2021 – Styles You’ll Love for Years

Happy Friday friends! I feel like I say this every week… but man has it been a busy week! And the weekend is going to get even busier…

BUT after this weekend things in our live should slow way down which I am immensely looking forward to. AND our youngest is finally starting to walk (he’s been in Physical Therapy getting a little helping hand) which have my spirits lifted way up! For those of you who have kids who were delayed in their gross motors you know how funny/exciting it is to see them finally walking independently. I came out of my room today and he was just casually walking down the hall like it was no big deal. Ha! But it was SUCH a big deal, and it has me hopeful that we are in the home stretch.


I asked you guys in my stories on Instagram if you’d rather see a denim short guide or a sandal guide, and the response was pretty much 50/50 SO I decided to do the shorts guide this week, and I’ll do my sandal guide next week so everyone is happy. 🙂 I aim to please!

Denim shorts are one of my absolute must haves for warmer weather. Where I’m at in the Midwest it gets HOT and super humid in the summer and when the temps reach the upper 90’s with 80% humidity the only thing I can bear to wear are shorts. I do love my linen and summer cotton shorts (I’ll do a non denim short guide soon!), but denim shorts are just so hearty so they can withstand the worst that 4 kids can throw at me and they’re comfy…

although I have learned over the years that not every pair of denim shorts is created equal. You want something that will stay up, that’s not so thin that it’ll wear out in only one summer, and that will make you feel good.

And a good pair of denim shorts are a major confidence booster!

I did do a denim short guide last year if you want to take a look at that one, and some of the styles I showed you will be in today’s post, but I’ve added a few more pairs to my rotation this summer so I wanted to give you an updated guide.

Okay enough chatter! If you’re curious about my measurements, you can check out this post.

Let’s get to the shorts!

Shop the Look

Notes: the color of my sandals is “sunbliss” and they run true to size. You can get 20% off my tee using code KARIN20, I’m wearing a Small.

The Shorts: Madewell Mom Jean in Willis Wash

Retail for: $69.50

My thoughts: As with all Madewell Denim (check out my Madewell Denim Guide here), these shorts are very soft and stretchy. They just do comfy denim SO well. I do really love the cut of these shorts as well… you’ll notice a trend here in this guide of a looser leg in all of the styles I chose and that’s because I really dislike denim shorts that are tight to the thigh… these are not that. I love that they have a higher waist paired with a more A line shape, and the raw hem keeps them from looking too much like actual mom jeans. In other words, it’s a classic shape with a fresh take. I stayed true to size with these in a 26 (I almost always wear a 26 in Madewell denim).

Shop the Look

Notes: My shirt is an older style from Christy Dawn so I linked to a few similar options. I have a review of the sandals here (they were gifted)

The Shorts: Abercrombie High Rise Mom Shorts in Medium Wash

Retail for: $59

My thoughts: These are just a tad bit more on the sexy side as opposed to the Madewell shorts. To be honest, for this mom of 4, I kind of appreciate a little va va voom in the wardrobe department ha! These shorts hug the thighs the most out of all of the styles I’ll show you, but I still find them to be very comfortable and stretchy. The distressing at the hem and throughout balances out the closer cut and still creates a flattering shape. The rise on these also doesn’t feel as high as some of the other styles so if you don’t love a super high rise then these are a great option. I got these in a size 27 which is what I always wear in Abercrombie denim.

Shop the Look

The Shorts: Agolde Dee Super High Rise Shorts in Exhibit

Retail for: $128

My thoughts: If you’ve followed my blog at ALL then you know these are my hands down, top fave denim shorts of all time (I featured the blue wash in last year’s denim short guide). Incidentally they are the most expensive pair I’m showing you. If you can swing the $128 then I will tell you that these jeans are absolutely worth it. They are incredibly comfortable, have the perfect rise, and length, and the side slit makes them just really flattering. I honestly can’t rave enough about these shorts. If you were to only buy one pair of denim shorts ever, this would be the pair I’d recommend. They run a tad small so I get mine in a 27.

Notes: my bag is from Polene – color is taupe. I linked to a few more affordable options.

Shop the Look

The Shorts: Free People You’re Unbelievable Short in Capital Blue

Retail for: $78

My thoughts: I really, really like these shorts. I appreciate the addition of a lighter wash to my wardrobe, and the exaggerated raw hem is a really fun take on a basic pair of jean shorts. These have a very similar fit to the Madewell shorts in the first set of photos, but I’d say the material on these is slightly more thick (but not in a bad way). They are still very stretchy and comfortable to wear though! I’m wearing them in a 26.

I purchased my tee secondhand and this exact style is no longer available so I linked to similar.

Shop the Look

The Shorts: Old Navy Extra High Waisted Sky High Cutoff Jean Shorts in Jane

Retail for: $39.99 (currently on sale for $30)

My thoughts: Longer shorts are very “in” at the moment, and I looked at a lot of styles before I finally settled on this pair from Old Navy. I liked that they nod to the trend, but they are still a very classic cut and style that will still look good when the trend has passed. And it’s nice to have a longer pair in rotation! These are very comfortable with thin and stretchy material, but they really do feel well made. Old Navy is hit or miss for me, but these are a definite hit! I always size down in Old Navy denim so I got these in a size 2.

Shop the Look

Notes: these shorts were gifted. The sandals run true to size (I’m wearing a 40).

The Shorts: Everlane Easy Jean Short in Deep Sea

Retail for: $45

My thoughts: I’ve been a big fan of the Easy Short (you can see my review of them in my Everlane short guide) for a couple of years now, and the newly released denim version is no different. These shorts are just… easy (he he). They literally live up to their namesake… they’re comfy, relaxed, and easy to wear. I do think that you need to size up in these shorts to make them work though. I have all of mine in a size 6 and the extra room gives them that laid back, slouchy easy look they claim to have.

Well there you have it! All of my 2021 denim short recommendations. You honestly can’t go wrong with a single pair of these shorts so definitely check them out. Did any of them stand out to you? Let me know in the comments below! Thanks for reading friends.

Until next time,


Leave a Comment


  1. 5.7.21
    Alison said:

    Do you have a dupe for the AGOLDE shorts?

    • 5.10.21
      Karin said:

      The Free People is probably the closest out of all of these, but I haven’t found anything yet that’s a true dupe.

  2. 6.5.21
    Patti said:

    Ugh… I absolutely hate high waisted jeans. Long or short. I grew up wearing high waisted bell bottom jeans and I just think that the new trend in mom jeans make you look so “dorky”. I just think that mid-rise is so much more flattering.

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