High waisted jeans made an enormous comeback in 2018 and are still going strong. I keep telling you guys that I’m giving fashion history lessons, and I’m sticking to it. All hail the high waist denim deities. So let us talk about Levi’s. I remember my mom always talking about her favorite 507’s and how (for most of my teen years) that I should be wearing Levi’s because of how great they are compared to the expensive True Religion and Rock Revivals I had to have in my closet (sorry Mom).
Levi’s are the alpha in the denim industry and are also responsible for the high waist style. Back in the 1940’s these bad boys made their debut for women who went to work during the war while the men were away. The high waist allowed these revolutionary women to remain modest ladies if they bent over while working.
Come the 50’s they were still worn because they accentuated the lovely lady curves and were given an iconic look courtesy of Marilyn Monroe who flaunted her high waited jeans with a belt and a tucked in shirt. The fad faded a tad in the 60’s and 70’s because bell bottoms became the focus.
Then in the 80’s Guess Jeans blow retro fashion out of the water with the skinny/ straight leg high wasited jeans in a variety of washes. I have a favorite pair of high wasited Guess jeans that you’ll see in my Outfit Of the Day Posts. Mom still wears her denim guess jeans and jackets from the 80’s. Fashion in a full circle there.
Anyway, high waist fades through the 90’s (with the exception of mom jeans) and early 2000’s but last year? They’re everywhere. I’m here to help you wear your high waisted jeans because they’re so lovely at accentuating curves and even hiding some areas! So let’s get started.
How To Wear High Waisted Jeans In The Summer
The first topic I want to talk about is how to wear high waisted jeans in the summer. Jeans really are a year round clothing item. It doesn’t matter how warm it is outside, you can wear jeans. Makes perfect attire for those days where it is warm when the sun is up but gets chilly once it goes down, you know?
The image on the left shows her high waisted jeans with a cute little white tank top. A v neck with buttons down the front that lead to a tie at the bottom. It’s cute, and shirts like these are really popular right now.
The image on the right shows high waisted mom jeans with a cute floral/ tie-dye off the shoulder crop to. (Hello ruffles!) She’s completed her look with a black Gucci belt, black heels, and a black bag. If you take a look at her pants, she has the bottoms of them rolled up, which is really the way to go for those super warm summer scorchers when you’re wearing pants.
Check out my Leopard Print Top outfit, I’m wearing high waisted Guess pants with this and it really makes for a fun summer night look. A nice pop of color seen in the shoes, a fun flirty print, the open back and sweet strapless top keeps you cool. High waisted jeans with your favorite summer tops are super cute and easy to wear! Pair them with a cute pair of sandals or heels and you’re ready to go!
How To Wear High Waisted Jeans In The Winter
The cooler winter months are when jeans see the most action so there is no reason to not wear your high waisted ones. If you look at these two outfits, they practically took whatever top that would be summer weather appropriate and added a sweater or jacket to them to be more suitable for those chilly days. One of my favorites is this White Teddy Bear Coat with my high waisted jeans, you can see it here!
Take a look at the image on the left. She is wearing a beige trench coat, over a black top tucked into high waisted jeans with rolled ankle cuffs. She picked black heeled ankle boots that match her belt and top, and a back pack that matches her coat. How easy is this look! You could wear this outfit with red or even white boots, or even pointed heels. Don’t forget to match your bag!
Then we have this look on the right, which screams cozy winter fashion. I love these big chunky turtleneck sweaters, and it looks stellar tucked into her high waisted jeans and beneath a trench coat. Emphasizing the big chunky look, she has even selected a big bag. Her shoes we can’t see, but a pair of pointy toe heels or sock boots would be what I would wear with this look. If you have a turtleneck or cowl neck sweater and a trench coat or even a pea coat you have what it takes to recreate this look with your high waisted jeans (regular jeans too)!
How To Wear High Waisted Jeans With Sneakers
So I wrote a how-to blog on wearing white sneakers. You can check it out that How To Wear White Sneakers here. I talked about how universal white sneakers are, and really the white sneaker and a pair of jeans is the most commonly worn combination in history- across all ages, across the world. But I wanted to make sure it was known that those favorite white tennis shoes can be worn with your favorite high waisted jeans also.
The image on the right looks like the most comfortable outfit besides a pair of sweats, doesn’t it?! She is wearing her high-waisted straight cut mom jeans with a black tee, a teddy bear jacket, and some sneakers that could probably serve well as running shoes. This look is a perfect example of how you don’t have to have a solid crisp white pair of shoes to wear them fashionably. She’s even added a striped bag for some extra color and pattern to her look. This is probably the easiest look to pull together! Can you imagine your favorite band tee or a graphic tucked into your jeans?
Then we have the picture on the right, which shows her wearing a long sleeve turtleneck tucked into her high waited jeans with white sneakers. Something important to note between these two images is the type of shoes they’re both wearing. Yes, both white sneakers but the look on the left look more like athletic shoes whereas if you ran in the shoes on the right you’d probably break your ankle with soles that thick! Easy look to recreate though, even if you wear a white tee, a white sweater, or some other white shirt. The point, is these jeans and these sneakers are such simple pieces to pair!
One of my Outfit Of The Day looks is me wearing a Striped Chunky Turtleneck Sweater with high waisted jeans and sneakers, give it a look. Would you wear it?
How To Wear High Waisted Jeans With Heels
Jeans and heels are magnificent together, regardless of wash, color, style, cut… they just work. So I wanted to share a couple of images that display cute ways to wear high wasited jeans with heels- which if you’ve noticed in several of these topics I’ve already talked about most of them are wearing heels with their outfit. I love my Miss Lola boots with the clear heel, you can see me wear them with my high waisted jeans in this perfect fall coat outfit here.
Left to right, right? On the left, I love this look for a casual but still cute day out outfit. She is wearing a simple black tee tucked into her distressed high waisted jeans, and a pair of simple black strappy heels. This would be cute with a favorite graphic tee!
To the right, she is wearing a sweet v-neck blouse tucked into her high waisted jeans, which has a hole in the knee, but I think between the strappy heels, the style of her top, and her top knot this look would be perfect for a girl’s night out, or even a date! I also love that she is carrying her bag, rather than holding it over her shoulder. It makes a statement, doesn’t it? Those 2 in 1 bags are awesome!
High Waisted Jeans For Different Occasions
I think it is safe to say that we all have jeans designated for specific occasions. I have my “nice” jeans and my “casual” jeans. So this part I wanted to show you that high waisted jeans can be more than just your stroll to the store or casual day with friends pants. You can dress high waisted jeans up with a nice shirt, sweater, or even a blazer. Check out my Pink Blazer with Highwaisted Jeans outfit of the day look!
The woman on the left, where do you think she’s going? She’s wearing black distressed high waisted jeans with a long sleeve button up blouse. Maybe lunch with friends? A coffee date (lucky guess?) or maybe she works somewhere that she can wear distressed jeans. The top dresses the outfit up! You could easily pair a nice collared button up with these even!
If you look at the outfit on the left, you see that her top is a probably that chiffon/ polyester material which is almost an instant dressy-upper (yes, I just made that up). Her top has either ruffled shoulder accents or maybe even a padding in them and it is probably a button up in the front. These shirts are pretty inexpensive and easy to find! The polka-dot pattern is cute and makes it a little dainty.
Hopefully this has inspired you or helped you try new ways to rock those favorite high waisted jeans of yours! I want to know how you wear yours- tell me below in the comment section!