How To Wear - May 19, 2019

10 Ways to Wear Denim Shorts

How To Style Jean Shorts

I’ll admit, it wasn’t until a few years ago that I actually felt comfortable wearing denim shorts. I could never find a pair that I felt comfortable and confident in. But after going through 12+ pairs of jean shorts that just never felt 100% *right*, I finally found a pair that I Love!

I think it’s safe to say that every girl has one part of her body that isn’t her favorite and for me, it’s my legs. So I’m VERY particular about shorts and hardly EVER wear them. But these jeans shorts are the first pair that actually felt and looked decent on me. and now I literally have them in every single wash and color they make because I love them so much!

With Summer basically here, I thought it would be fun to do a “Weekly Outfit Ideas” round up on how to were and style denim shorts. I’ll be styling this lighter wash pair in 7+ looks below for yall! Let me know in the comment which look is your favorite!

jean shorts summer outfit with smocked floral top and white denim jacket

Jeans Shorts with a Printed Top + White Denim Jacket

Sometimes when it’s REALLY freaking hot, putting on long jeans with that new cute top you just purchased just ISN’T GOING TO HAPPEN. In which case, I always resort to my cutoff shorts (if the dress code permits). Especially for when I’m dressing up for something during the day! I paired this look with a white denim jacket make it look a little more dressed up and put together. And although I don’t have them on here, I added some hot pink statement earrings to really make the pink POP!

Outfit Details: Smocked Floral Strappy Top (wearing size XS, fits short) // White Denim Jacket // Tan Wedges (will be living in these this summer! fit TTS) // Tan Wooden Handled Bag (love how perfectly this bag matches with these shoes!)

I’m including a photo without the jacket so you can see the detailing of the top! 

jean shorts summer outfit with smocked floral top

jean shorts outfit with lightweight sweater

Denim cutoff shorts with an oversized, Lightweight Sweater

Something about wearing an oversized (long-sleeved) top with high-waisted shorts just looks so #effortless, don’t you think! While I’m at the beach, I love wearing looks like this but like also pairing my denim shorts with a long-sleeved graphic tee and a scarf or something in my hair – it makes for the perfect laid-back chic look!

Outfit Details: Rust Colored Sweater (fits oversized, wearing size XXS – see it with skinny jeans in this outfit here) // Tan Flat Strap Sandals (old – similar here for $80) // Printed Headband // Circle Straw Bag

DENIM shorts outfit with utility shirt tucked in and sneakers

Jean Shorts with a Button-up Shirt (Tied-Up or Tucked-in)

There truly is something about a longer-sleeved top with shorter shorts that I love! Maybe it’s the juxtaposition or the fact that both these tops not fitted and so it looks more relaxed. Regardless of the reason, I just love how chic the combo looks. And I paired sneakers with this look to make it even more casual. But I think loafers or sandals would look just as cute!

Outfit Details: Olive Utility Shirt (wearing size 2, fits true to size) // Brown Belt // White Platform Converse // Circle Straw Bag

jean shorts outfit with white booties and black oversized blazer

Oversized Blazer + Statement Booties

Not gonna lie, this look was a little out of my comfort zone but once I warmed up to the idea of wearing booties with shorts, I was ALL ABOUT IT. And something about the blazer somehow balances out the whole look, giving it this super chic and put-together vibe. All in all, I’m obsessed with this look! I’d probably add some sort of edge statement-ish necklace, but I didn’t have one that looked right. Would you wear this?

Outfit Details:  Oversized Blazer (old – similar here) // Black Fitted, square-neck Tank (wearing size XS) // Dee Keller White Pointed Toe Bootie (old – similar here) // Black Quilted Crossbody Bag (love this one by Tory Burch and this one by Rebecca Minkoff)

jean shorts outfit with jean jacket

Wear Denim Shorts with More Denim

I got a text from one of my girlfriends the other day asking me, “wait real quick, is it cute slash okay to wear a denim jacket with jean shorts?” To which I responded, “HECK YES SO CUTE GO FOR IT!” but really I absolutely love denim on denim! I think the trick  is just added in a print where you can (like with accessories or shoes like I did here!) or another neutral or accent color to sort of tie it all together!

Outfit Details: Oversized Distressed Denim Jacket // Black Fitted, square-neck Tank (wearing size XS) // Western Belt // Snake Print Flat Sandals  (fit true to size, $39) // White Crossbody Bag (old –  similar here)

denim cutoffs with camp jacket and Gucci loafers

Denim Cutoffs and Camo print

I’ve had this camp jacket since like 2014 and I’ve actually worn it WAY more than I would have anticipated.  My style is usually pretty classy and sophisticated but I do have days where I like to be a little more edgy and spunky. I love the bit of interest the camo print adds to this look – especially when paired with the leather and gold loafers! This graphic tee is just the right amount of “stuff going on” if you ask me – I love that it’s a neutral grey with simple black lettering on it because it makes it easy to stye with different  outfits.

Outfit Details: Camo Printed Jacket (old – similar here) // California Graphic Tee (wearing size 2) // Gucci Mules (Sam Edelman version here) // Black Quilted Crossbody Bag (love this one by Tory Burch and this one by Rebecca Minkoff)

jean shorts outfit with long grey cardigan

Denim Shorts with a Longer Cardigan and White Tee

I was a little hesitant to try pair a cardigan that’s longer than my shorts (since I’m so short, I thought it would make me look stumpy). But I actually love how this looks. The different length of the shorts and cardigan actually looks really cute, don’t you think? I really wanted to pair this white-tee-and-shorts combo with a lightweight, natural cardigan but I didn’t have one. I feel like that would be SUCH a cute look!

Outfit Details: Grey Mid-Length Cardigan (old –  similar here) // White V-Neck Tee // Gucci Mules (Sam Edelman version here) // Black Quilted Crossbody Bag (love this one by Tory Burch and this one by Rebecca Minkoff)

Denim Shorts + Army Jacket + Wedges

This look is perfect for spring or summer (you can easily take the jacket off and just go with the tee) and I love adding a wedge with shorts because it elongates your leg – which I need being short and all, ha! I love the tan, green and black color pairing so this look is right up my alley. Change up the look by adding different wedges or different short styles (distressed, dark wash, cuffed) and make it your own!

Outfit Details: Striped Tee // Green Army Jacket // Distressed Denim Shorts // Tan Wedges // Tan Bag


denim shorts, white tie-front top, red banadana, cognac wedges

Denim Shorts with a White Button-Up and Wedges

I don’t know what took me so long, but I got this short-sleeved white button-up last year and I can’t stop wearing it. Check out this blog post  to see more ways to style it! It’s such a GREAT wardrobe staple!