Fall Denim Roundup – the Only 4 Pairs You’ll Need

And it’s Wednesday! We have a soccer game tonight for our oldest and it’s just the funniest thing to see all of those 6 year olds running in one big clump up and down the field ha! The games have been such a fun thing to do together as a family, but I’m also kind of glad they are coming to an end. I really want these last few weeks of summer vacation to be filled with the outdoors. We made it to the beach yesterday and I’m hoping we can make it down to the river this weekend. Late August/Early September is one of my favorite times of the year and I’m just so eager to soak up all of it that we can.

This time of year I live in my jeans… and I wanted to do this fall denim roundup today because I feel like I talk about jeans A LOT on here, and over the years I’ve shared a lot of different styles. So what I’m sharing today is a roundup of the top 4 styles that I own. These are the 4 styles that I reach for over and over and the pairs that I would keep if I had to get rid of everything else.

So if you’ve ever wondered what jeans I prefer the most, the jeans in this fall denim roundup are it.

My #1: Everlane 90’s Cheeky Jean

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Sizing Notes: Jeans – TTS (26 ankle), Sandals – TTS, Tee – Medium

Bag was gifted as was the Necklace (use code HEYKARINEMILY to get 15% off)

This shouldn’t come as a surprise to anyone, but the Everlane 90’s Cheeky are my #1 can’t live without jeans. I’ve already reviewed them in my Everlane Denim Guide so I won’t go in depth here, but I want to tell you why they are my favorite. They are extremely comfortable… the kind of jeans you can wear all day and still be comfortable. The rise is the perfect high rise, the shape is the perfect subtle mom jean and they come in a ton of washes (I have them in 4 washes – that’s how much I love them!). The length is also perfect for wearing with boots.

They run true to size so I’d go with your waist size (they also have a curvy style)

My #2: Madewell Perfect Vintage Jeans

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Sizing Notes: Tee – Medium, Jeans – One Size Down (25), Cardigan – Small, Sandals – One Size Down (39)

Sunglasses were gifted. Bag is Polene

Another not surprise is these perfect vintage jeans from Madewell. Again, I already reviewed them in my Madewell Denim Guide so I won’t go into the specs too much here, but you guys… I call these my magic jeans and they truly are. The are the comfiest jeans I own… they are SO stretchy, but they don’t slip down throughout the day. I also love that these have a slim straight fit so they kind of satisfy that skinny jean itch while being a bit more current (and way more comfy in my opinion).

They run big – they should be snug when you first get them because they’ll stretch out over time. I go down one size in mine.

My #3: Levi’s Ribcage Straight Ankle Jeans

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Sizing Notes: Jeans – Go up 2 sizes, Sweater – Small, Sandals – run a half size big

If the link to the sweater above doesn’t work, try this one

If you saw my Levi’s Denim Guide then this style may come as a surprise to you because I didn’t rate them as my favorite pair of Levi’s, BUT while they aren’t my favorite style of Levi’s, I reach for these most often because of the fit. My other style of Levi’s are fairly similar in look to the Everlane Cheeky’s, and these fill a different hole in my wardrobe with the extreme high rise and the wider leg. They’re also a thicker denim so great for cooler weather and they’re really comfy to wear. I just love the way these look and they are in constant rotation in my wardrobe.

In my opinion these run really small. I go up two sizes in them and while there is still a little room in the waist, one size down is WAY too tight. I typically wear a 26 and I wear this style in a 28.

Last, but not least: Agolde 90’s Straight Jean

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Sizing Notes: Jeans – TTS (26), Shirt – Small, Mary Janes – TTS (old colorway so I linked similar), Bag is an old colorway so I linked similar. Sunglasses were gifted.

These are a newer style to my closet so I may be jumping the gun a bit here, but the minute I put these on I was hooked. They are 100% cotton, but the BEST kind of 100% cotton. They are so soft, comfortable, and they fit so, so well. They are the perfect pair of jeans to wear with cozy oversized sweaters and I imagine I’ll be living in them until the weather doesn’t allow for ripped jeans. 🙂

I got these in my true size, and I thought maybe I’d want to size down so I ordered a size down to test it, and I actually prefer these in your true size. They are slightly oversized, but because they are 100% cotton they won’t stretch out. The size down was just a bit too tight. Plus, the charm of these jeans are the oversized fit so you don’t want to lose that by sizing down.

Honorable mention: Levi’s Wedgie Fit

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Sizing Details: Jeans – size up (27), Sweater – size down (XS), Sandals – TTS

I just had to mention these jeans in this fall denim roundup as well because they are another favorite, but they are similar enough to the 90’s cheeky that I had to prioritize those. These are a great option if you don’t love the 90’s cheeky! You can see my review in my Levi’s Denim Guide.

That’s all I’ve got for you guys today! I hope you enjoyed this look at my fall denim roundup. Do you have a style of jeans you reach for over and over? Let me know what they are in the comments!

Until next time,


Leave a Comment


  1. 8.14.21
    Erin said:

    Hi Karin! Does the waist on Madewell’s Perfect Vintage Jean stretch out at all with wear? I find that they fit me everywhere except the waist, which is a little tight.

    • 8.16.21
      Karin said:

      Hi Erin! Yes they do – not a ton but if they are a little tight then they should loosen up with time!

      • 8.16.21
        Erin said:

        Thank you!

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