Do you love the comfort and effortless style of 90s jeans but aren’t sure what to wear them with? Here’s how to wear 90s jeans in an easy, effortless way that’s suitable for every day!
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Whether it’s through long-overdue Netflix binges or throwback social media posts of 90s fashion icons, the 90s jeans outfit is making a resurgence.
My interest in 90s jeans started during my first-time binge of Dawson’s Creek, which had innocently appeared on my Netflix recommended page, and I thought, “what the heck, I’ll try it out.” Plus, it’s been super fun reading people’s reactions and comments on the subReddit (people have OPINIONS).
Anyways, since the show takes place, and was filmed, in the late 90s and early 2000s, it made me think about 90s fashion in general.
Even though I’m a 90s kid, I was a baby when these clothes were in style, and my five-year-old eyes were in no place to appreciate some of the cool aesthetics and silhouettes of the time (terrible 90s photos of my parents, complete with red-eye, didn’t help either).
Plus, I think I was confusing 90s fashion with 2000s fashion, which, let’s face it, was not my favorite era (cue chunky flip flops…).
Whether these are mom jeans, boyfriend jeans, or jeans by any other name, 90s jeans tend to be high-waisted, loose, and often fairly baggy.
This makes them a challenge to style, but since they’re so comfortable, it’s super worth it to learn how. Here are my top tips for figuring out how to wear 90s jeans in your everyday outfits!
Your 90s Jeans Outfit Starts With the Right Jeans
Before we get into how to style 90s jeans, let’s take a look at how to actually choose the right pair first.
In my case, when I opened up my Aritzia newsletter and saw “90s jeans” under New Arrivals, I clicked on it. And the jeans looked GREAT. So, off I went to Aritzia to try them on.
Unfortunately, nothing fit right, no matter how many brands, different fabrics, and fits I tried. I’ve always wanted to try something from Reformation, but I’d recently had an online shopping debacle (“but it looked so good on the model!”) that I didn’t want to risk ordering online.
My friend told me that American Eagle was having a sale, so I headed over and got this fantastic pair for a fraction of the price as the Aritzia jeans.
Of course, I wasn’t sure how these types of jeans would look on me, what I’d wear them with, or whether I’d even like them after I tried them on, so I didn’t think it was worth spending $250 plus on jeans like this.
This is why I recommend trying a cheaper version of a trend first if you’re on the fence (which also helps you stop impulse buying a super expensive pair). But after trying these, I’ve since gotten more American Eagle pants and have been quite pleased with them!
And if you’re not a fan of super baggy styles, check out slightly slimmer versions of boyfriend jeans, or look into getting a pair of mom jeans.
Another tip that I like to give is that you don’t need to buy items just because they’re “trendy.” In this case, I had already wanted a looser pair of jeans that were super comfortable.
Use trends to your advantage, and if there’s something you really like that happens to be trendy, then that means you have a lot of options to choose from! I did this years ago when smoking shoes were on-trend, and I got the most comfortable pair ever from Nine West that I still wear all the time.
This also means that you may not get the usual 90s jeans brands that you’d wear for your other jeans.
If you’d like to try out some 90s jeans for yourself and re-live the 90s (or live them for the first time), check out how I styled these jeans below (I’m wearing a 90s boyfriend style).
At the end of the day, you want to get a pair of jeans in a wash you’ll like, that fits you well and that you’re comfortable in.
How to Wear Baggy Jeans
Some ideas for styling this type of pant would be with tennis shoes and a top that is tight or that cinches at the waist. This is the outfit I’m wearing below, and it’s super comfortable for walking around with friends.
I paired the jeans with a linen cardigan I bought at the thrift store for a layered and sweat-proof summer outfit. You could also tuck in a looser top and pair it all with some cool sunglasses.
For fall or winter, you can pair the jeans with a chunky sweater for even more vintage vibes. To show off the jeans the best, go for a jacket with a higher cut and a vintage aesthetic like a cropped jacket.
A leather jacket would work really well too, especially a moto-style leather jacket. You could also try a denim sherpa jacket to keep warm but stay with the vintage aesthetic.
For this one, you’ll want to do a denim-on-denim look with enough of a contrast in color between your jacket and your jeans.
Here are some more ways to wear baggy jeans from YouTuber Audrey Coyne:
Cute 90s Outfit Ideas
For my look, I’ve gone with a 90s acid wash jeans outfit. To complement the color of the jeans, I’ve chosen an orange spaghetti strap cami à la your favorite 90s TV show.
Some other tops you could wear include a cropped t-shirt, graphic tee, or cropped sweatshirt so you can best show the shape of the jeans. Another good idea is to wear an oversized shirt and then tie it at the waist.
As for jackets, you could get a 90s or vintage style jacket to complete the look, such as a varsity jacket or a sherpa-lined denim jacket that matches the wash of your jeans.
For the rest of this post, I’ll go through each section of your outfit and give you some ideas that can help kickstart your outfit ideas.
For the shoes in my 90s jeans look, I usually opt for a pair of white tennis shoes or Converse-style sneakers. I like to go for simple, neutral-tone sneakers for this type of outfit to keep it wearable and not too overwhelming.
Keds also work quite well, as do classic Oxfords for an evening out, especially if you’re wearing the outfit with a blazer like I did.
Due to their cut, the jeans do look best when draped over top of boots rather than tucked into them. Now that fall’s come around, I’ve been wearing these over-ankle boots and even over my ankle-length winter boots.
And no matter the season, you can wear these jeans unrolled for a more straight-leg look or roll up the bottoms to better show your shoes.
Since the boyfriend fit of the jeans is a bit loose around the waist, I added my go-to braided skinny belt for a better fit. I added some cool hoop earrings, a chunky bracelet, and draped a thrift blazer over my shoulders for a more casual look.
Some good jewelry to pair with this outfit would be a chunky bracelet, mismatched earrings, or stud earrings.
If you want to go all-out 90s, then get a set of resin rings, which were a huge 90s trend that’s made a comeback this year.
For bags to wear with this type of outfit, I’d keep the outfit simple with a cross-body bag or a one-toned satchel. You could also go for a tote bag as long as you keep it simple.
Remember, to keep a 90s outfit as wearable and as modern as possible, you want to let the jeans and top shine while the rest of your accessories complement (rather than take away from) your outfit.
How to Wear 90s Jeans -Final Thoughts
Learning how to style 90s jeans might take some trial and error, but once you get the hang of it, you’ll love how versatile and comfortable these jeans are.
My favorite part about 90s jeans is that they’re loose and literally feel like pajamas, but can look so cool and stylish with little effort. I also love that you can dress them up or down.
Remember that there’s no “right” way when it comes to how to wear 90s jeans—these are all just ideas meant to give you inspiration so you can find the style that works best for you.
What’s your favorite way to style 90s jeans?
Posts Related to How to Wear 90s Jeans:
- Boyfriend vs Mom Jeans: Which Should You Buy?
- The Beginner’s Guide to Creating a Winter Capsule Wardrobe (That You’ll Actually Like)
- How To Find Your Perfect Skinny Jeans and Blazer Outfit