Jean Shorts Guide: Best Denim Shorts to Buy this Summer

Why does it feel so hard to find the perfect pair of jean shorts? Why does every single brand fit differently? Seriously, the size shorts in my closet range from 24 – 27. It’s never about the size, always about how you FEEL in them and the fit! Over the past few years, I’m finally satisfied with my collection – there’s a style for every vibe & activity. High waist, low rise, medium wash, dark wash, frayed, distressed – styles that fit complete every outfit.

The Holy Grail – Levi Wedgie Shorts

$$ Mid-Rise, Medium
Wash, Lightly Frayed Cutoffs

If you could only wear one pair of jean shorts all summer, THESE would be the ones. There’s not a single style they don’t blend with. The mid-rise & medium color makes it so easy to coordinate. Wear them with a casual tank or tee, tucked in or not. The mid-rise but not *quite* high rise still allows you to pair over a bikini as a cover up. Comfortable, quality,
& classic. The Levi pocket design is flattering for every booty! I’ve had mine for 2 years and probably worn close to 200 times and they still feel like Day 1!

Fit: Levi’s run small, wearing a 28, but wish I had a 27. Recommend going 1 size up, but if you really don’t like tight shorts, go two sizes up.

The Dark Wash Distressed & Cozy – Blank NYC

$$ Low Rise, Dark Wash,
Stretch Denim, Distressed

Ahhhh, these are so comfortable. Perfect for late night ice cream runs, and summer activities like biking or walking around all day. The stretch is the perfect amount to be comfortable but don’t stretch out to the point of they need to be washed every time you wear them. For low rise shorts, I recommend pairing with looser fitting tanks and blouses. Tighter fitting tops
are more flattering with high-waisted shorts than accentuate your waist.

Fit: These run small, recommend sizing down. Wearing a 25.

The Light Wash
Distressed & High – Articles of Society

$ High Rise, Light
Wash, Distressed, Frayed Cutoffs

Finally – the perfect pair of high rise! Hitting right on the belly button, made to bring attention to your waistline. This is the
perfect pair to wear with a crop top or a tight fitting tank top. High rise style is more of my street or festival style.

Fit: These shorts don’t have too much stretch and run TTS / a little small. Wearing a 27 (I sized up, but I don’t like a tight tight fit).

The Short Shorts – One Teaspoon #2

$$$ Low Rise, Medium
Wash, Distressed, Frayed Cutoffs

These are the Jessica Simpson daisy duke short shorts of my collection. I love how they cut up on the side to elongate the legs, but still cover the booty (ever so slightly) in the back. There’s a perfect amount of fringe and distressed look to compliment the short style. I love wearing these as a cover up to the pool with a one piece! Also pairs nicely with a loose-fitting tee for a casual, daily OOTD look.

Fit: They don’t have stretch, and run big. I recommend sizing down once. Wearing a 25.

The Conservative – Joe’s Jeans

$ Mid Rise, Darkest
Wash, Stretch Denim, Cuffed

I call these my “family friendly” pair. They have a longer inseam than the other pairs featured. What’s nice is you can adjust the length of the shorts by how much you cuff them – so you can make them short if you want to. A classic cuffed design without the distressed look, they match nicer blouses in addition to casual tees. These have tons of stretch and are super comfortable. I got these last year at Nordstrom Rack – a haven for designer jean shorts discounted. I couldn’t find the same pair this year, but linked similar styles.

Joe’s Jeans Fit: Run big! Recommend sizing down or two. They stretch on the first wear if you get them where they feel “comfortable” in the store. I didn’t know they would stretch so much, and bought a 26 and a 25 would fit better.

The Pair Under $30 – Forever 21

$ Mid Rise, Medium
Wash, Frayed

Forever 21 is always a treasure hunt – sometimes you are in the mood and other times not so much. It’s a haven for cheap jean shorts in a variety of styles. Recommend trying a style that you would normally go for – frayed, high waist, overly distressed – because you can get most jean shorts under $15 – $30.

Fit: Wearing a size M here, equivalent to a 27. TTS.

White Denim Styles –
2 pairs for different occasions

$ High Rise Distressed Street Style – Forever 21

These are the most distressed pair I own, and are perfect for a festival look or wearing on a boat with a bikini. The white & high
rise combo is very flattering and the major distressed look with holes elongate your legs! It’s a win-win for a more casual and street style look.

Fit: Runs small, wearing a size M here, which according to their size chart is 27-28.

$ Low Rise Rolled Polished Look – J.Crew

For a more polished look, J.Crew is always a classic. This cuffed pair is very stretchy & comfortable. Looks adorable with a preppy
print – floral or gingham!

Fit: Runs HUGE! Wearing a size 24, size down at least once
and possibly twice (I did).

My next Obsession: TopShop Kiri Shorts

$ High Rise, Medium
Wash, Frayed Cutoffs


As you can see, I don’t need any more jean shorts. But that doesn’t stop me from wanting another pair. I
resisted the urge of buying these at Nordstrom the other week, but totally worth mentioning here for you (including a dressing room try on pic!) They compete with the Levi Wedgie style – I would say a perfect blend in between the Levi Wedgie and the One Teaspoon Low Rise. They are frayed like the One Teaspoon and cut similarly, but have a high rise like the Levi’s. If these go
on sale, I will DEFINITELY be purchasing!

Fit: Runs small, go one or two sizes up. I’m wearing a 6 here, but because they didn’t have a 4
in stock. That would have fit better!

Which jean short style do you wear most?

Hi, I'm Anna!

Welcome to the corner of the internet where you’ll find boho & bright style, travel adventures, and life in my latest “hometown” – Nashville, Tennessee. My love and I recently bought a house – and we’re taking on the renovations ourselves! You’ll be seeing more home content here – from DIY tutorials to home decor inspiration. We have a LOT of ideas for this house, implementing slowly one room at a time!

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