I Tried On 30+ Pairs of Non-Skinny Jeans, Here Are My Winners!

Today, we’re stepping outside of the DIY box to talk about fashion. I don’t consider myself to be a fashionable gal. It’s just not my thing. I don’t really enjoy shopping and some of the items in my closet are from high school. Finn loves getting new pieces for his wardrobe every season, but I rarely shop for clothes.

How to install vertical shiplap
Me & my skinny jeans

However, after having two kids and then focusing on my health in 2022, a lot of my old pants just didn’t fit anymore. I tossed a few pairs of too-big and too-worn jeans and added “buy new jeans” on my to-do list. But, what the heck to buy? My closet only consisted of skinny jeans and these days they’re considered “out.” I’m not one to follow trends, however, I was intrigued by the idea of adding a few pairs of non-skinny jeans to my wardrobe.

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I ended up polling my Instagram community to get the low down on where the heck to shop and what to buy. Instantly, I was flooded with messages from other ladies who felt just as clueless as me. How the heck do you wear some of these new baggier styles without looking like you’re wearing a potato sack? And what about shoes? How do you pair them with some of these wider legs? I volunteered to do the heavy lifting for you and find the best non-skinny jeans out there…

Your Favorite Retailers

Here’s the list of brands and retailers that you recommended in my pursuit of the best non-skinny jeans…

My Body Type

The best non-skinny jeans to try

Before I get started, I want to share a bit about my body type for reference. I’m a mom of two little ones and I’m a fan of a higher waist on my pants, so my booty isn’t hanging out when I’m on the floor playing with them. I consider my body shape to be kinda straight up and down (not much of a waist here) with thinner legs, a thicker middle, and a non-existent booty. I’m also on the taller side at 5’8″.

In terms of sizing, I had no idea what the heck my pant size was anymore and that’s why I knew that I had to do in-person shopping to figure out my size at each retailer. In the end, I wore a 4/6 or 27/28 at most retailers. I’ll note the sizing of all of the pairs I tried on below.

My Big Shopping Day

I blocked off two to three hours on my calendar on a random Tuesday to get ‘er done. If you’re going in-store, I recommend trying to go during a non-busy window. I walked in the door at 10am, as soon as they opened, and I was the only one shopping. Perfect. My best advice is to approach a sales associate, tell them you’re looking to venture out of wearing only skinny pants, and have them explain their styles and cuts to you. Everyone I interacted with was super helpful! Or, take a look at the ones I found and order a bunch of sizes and styles online and make some returns.

Savings Tip: Many of these retailers will give you a discount or money off if you bring in a pair of old jeans to recycle!


Here’s what I tried on at the first store I visited, Madewell. This was the most popular recommendation from my community and everyone suggested I try the “Perfect Vintage Jean.” But, as you’ll see, the PVJ comes in various styles too.

The Perfect Vintage Jean
Finding the best non skinny jeans

Perfect Vintage Jeans, Earlside Wash, Raw Hem (size 27)

Okay, so this is where I started – trying on the perfect vintage jean. At first, I went for my normal size (28) and they just felt so baggy. I thought, “Okay, this is just how the style is, so go with it.” But, then I showed the sales associate and she said, “Um, nope. They’re supposed to hug you more than that!”. I sized down and they were actually good!

This seems like a very nice tip-toe out of the skinny jean. Tight throughout the legs and then a little straight at the bottom. These came right up to my belly button, so definitely a high-rise.

The Perfect Vintage, Wide-Leg Crop Jean
Wide cropped jeans

The Perfect Vintage Wide Leg Crop, Cresslow Wash, Size 28 (should have sized down in these for a snugger fit)

Next, I tried on these, and whoa…I was not ready for them. These were a bit outside of my comfort zone and not the most flattering for me. I quickly took them off. But, I think with a bit more practice wearing non-skinny pants, I could work my way up to a style like this.

The Perfect Vintage, Straight Jean
Finding the best non-skinny jeans

The Perfect Vintage Straight Jean, Lunar Wash (size 27)

These were another surprise like for me. Not too rigid and not too stretchy…a good in-between. The legs are a bit wider than the regular perfect vintage jean. Overall, a cute style!

Mid-Rise Kick Out
Finding the best non-skinny jeans the mid-rise kick out from Madewell

Mid-Rise Kick Out Crop, Raw-Hem, Cherryville Wash (size 27)

These jeans ended up being a favorite of mine and I was super surprised! They’re snug and flattering through the butt, hips, and thighs and they have a cute little flair at the bottom. I was surprised that I liked the cropped look so much, but I think it’s a fun way to show off cool sneakers, flats, or booties. Overall, they were one of my faves from the day!

The Mid-Rise Perfect Vintage Jean
The best non-skinny jeans to buy

Mid-Rise Perfect Vintage Jean, Knowland Wash (size 27) // Sweater (size medium) // Blue Suede Booties

Again, another winner for me! These are very similar to the regular perfect vintage jean, but they don’t come up quite as high. Plus, they have a bit more stretch to them. If you look at the bottom, they’re really not that different from regular ol’ skinny jeans, so I think these are a good pair to try if you’re a non-skinny jean newbie like me!

Abercrombie & Fitch

Abercrombie was another popular suggestion and I’ll be honest, I haven’t really shopped at Abercrombie since high school! It’s very different all these years later and the price points were lower than Madewell, which was nice to see. Overall, I was actually very impressed with how Abercrombie has evolved over the past 15 years.

Ultra High Rise, The ’90s Straight
the best non-skinny jeans to buy in 2023

Ultra High Rise ’90s Straight, Black (size 27)

Okay, onto Abercrombie jeans, which was a new learning curve when it came to their styles. For most of their jeans, they also have “curve love” versions. This helps keeps things tight at the waist and throughout the hips, without giving you a gap in the waistband of your jeans. Since I’m not super curvy, I opted for non-curve love versions…but it might work well for your body type! Oh, and be sure to check online because they have soooo many colors available online as opposed to in-store.

These were not my favorite and I think it’s because they just felt kinda baggy throughout the hips and calves. There was just too much overall fabric for me. I know the rage is to wear tight tops and cropped shirts with pants like these, but I’m not so certain I can pull that off. These were a no.

Ultra High Rise ’90s Slim Straight
My best non-skinny jeans suggestions to wear in 2023

Ultra High Rise ’90s Slim Straight, Light (size 27)

These are similar to the above jeans, but that “slim” really made them feel a lot better. Not quite as baggy throughout the hips. These sat at my belly button and were snug all the way through, until the knee, where they went into a straight leg. Again, these are a really nice way to tip-toe away from skinny jeans and at a good price point!

High Rise, The Mom Jean
the high rise mom jean from abercrombie and fitch

High Rise Mom Jean, Medium (size 27)

At first, I thought these were cropped jeans, but I think these were just a tad short on me. They offer extra short, short, regular, long, and extra long online, but didn’t have all of those variations in store. Overall, these were pretty good! Another pair that sits right about the belly button for that high-rise look. If they had these in long, I probably would have scooped them up.

High Rise, The Mom Short

The Mom Short, Light / Medium Destroy (size 28)

Okay, I know I’m supposed to be chatting about the best non-skinny jeans to buy in this blog post, but I wanted to share some jean shorts I picked up along the way too! As long as I was trying all of these pants, I grabbed some jean shorts too and I really liked them! These are the same style, just in different colors. They come up high near your belly button and then get a bit looser in the thighs. Overall, I really liked these!

The Dad Short (It’s A No For Me…)
The dad short from abercrombie and fitch

The High Rise Dad Short, Medium (size 27)

I grabbed both a mom short and a dad short (not quite sure what they’re trying to say about parents these days…), and immediately took them off. I just don’t have the body type, or on-trend style, to pull these off.


My last spot during my shopping spree was Evereve. This is a new-to-me store and many of you raved about it. Essentially, it’s a boutique that carries multiple high-end brands of clothing. If you want to try a bunch of different brands all at once, this might be the best spot to check out.

By the time I got to Evereve, I already had a few straight jeans purchased, so here I decided to go way outside the box with wider leg styles…

Paige, Laurel Canyon, Mid-Rise
Paige laurel canyon boot cut

Paige Laurel Canyon Jeans (size 27)

Oh man, these brought me right back to high school when I wore flare jeans just about every single day! Remember when it would be rainy or snowy and the bottoms would sop up all of the slush? The worst! I thought these were really cute and comfortable, but I just didn’t feel ready to dive back into flare jeans just yet.

Citizens of Humanity, Lilah High Rise Bootcut
Finding the best non-skinny jeans

Citizens of Humanity, Lilah Bootcut Jean, Morella Color (size 27)

I really loved these jeans! I think they’re a good mix between a straight and a flare leg with the bootcut style. I didn’t end up getting them, but they are worth checking out if you’re looking for a cozy bootcut.

The Best Non-Skinny Jeans (For Me)

In the end, here were my top picks from my big day of shopping for the best non-skinny jeans.

the best non-skinny jeans to try

The Perfect Vintage Jean // Kick-Out Crop // Mid-Rise Perfect Vintage // Ultra High-Rise Slim Straight

From my experience, I found that there are lots of options that give you the feel of a skinny jean (tight through hips, butt, and thighs), but have a slight opening from the knee down. I went into this experiment worried that I would be wearing baggy pants from my waist down, but that’s not the case!

I’m happy with my haul of jeans and I might even try to venture into flare or wide-leg jeans soon. Maybe.

Shoes To Pair With My New Jeans

Before I go, I have to address a question that I had going into the non-skinny jeans world. What the heck do you do for shoes?

Now that spring is approaching, I think it’s a tad easier to wear these styles because you can reach for cute sneakers, loafers, booties, or sandals. But, I’m not totally sure I could pull off these jeans with snow boots and thick socks. Here are the shoes I’ve been reaching for over and over again when I wear my new jeans…

I hope this was helpful on your own jean journey! Please let me know some of your faves, so I can try them out myself!


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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