Wardrobe Essentials: Jeans

I thought it would be fun extension of my weekly outfit posts to dedicate an entire post to each of my most worn items. My wardrobe essentials. In these posts I’ll share everything from why I purchased them, to how they fit, to how I’ve styled them.

To kick of the series, I decided to start with my jeans. Because it seems just about everyone considers denim a wardrobe essential. But boy, is it hard to find good ones. When they’re good, they’re so good and when they’re bad, they’re so bad.

Since late spring, I have worn only one style of jeans. The Madewell Cruiser.

I decided about a year ago that I just wanted to find one basic pair of jeans. Not too skinny, not too boyfriend, not distressed, not too dark, not too light. I first purchased the Levi’s Wedgie Fit, which I almost loved. They were pretty dang close. The fit was great and they sure were flattering, but I never fell in love with the frayed hem. Eventually, my personal preference on that tiny detail won and I sold them earlier in the fall. My full review is here.

I don’t remember how I first discovered this particular Madewell style, but I tracked them down on Poshmark and bought a pair secondhand.


It took three tries to get the right size, but luckily they resell easily. I first tried the 29 and they were more of a boyfriend fit. I kept them for a while as an alternative to the more fitted Levi’s, which turned out to be perfect during warmer months. I then stumbled across a pair in size 27 on Poshmark, so I bought those. While I can get them on, they are a little too snug for all-day comfort. So, I kept browsing (aka stalking) Poshmark and finally found the 28’s. It was my Goldilocks moment. I am a true 28, so I say these run true to size.

Side note: If you choose to buy secondhand, search Straight Leg Crop as that’s what the tag inside the waistband says. Also, there are some seasons that were not 100% cotton, so that’s something to watch for too.

What I Like

My favorite thing about these jeans are that they’re 100% cotton, so they feel like real denim. Being short, the cropped length of the Cruiser jeans works out to be a full length pant on me. I also love the 10″ rise for tucking in and being able to sit and bend over without worrying my undies are hanging out.

What I Don’t Like

Honestly, not much. If I had it my way, they would be about an inch and a half shorter so I wouldn’t have to cuff them. I also don’t know that they would dress up as well as a darker wash, but I have other bottoms I wear in those situations.


I don’t think there are many styling secrets to jeans, which is what makes them a wardrobe essential. For me, when putting together an outfit with jeans I try to make sure I watch the little details – a tuck, a belt, a necklace, cute shoes – one or two of those elements always take it up a notch.

I wear these typically twice a week to work and on weekends. They work well with everything from flips flops to Birkenstocks to clogs to ankle boots to velvet heels. I also have discovered a new found love of fully tucking my shirts into these high-waisted jeans for a totally different feel to an outfit.

For work, I tend to wear my jeans with a sweater or a tucked in top and boots or heels. I also love the look of denim and a blazer, so I’ll throw that into the mix every now and then.

For weekends, I throw on a t-shirt or sweatshirt and comfortable shoes. If we’re going out and about I add a necklace to pull the look together.

How many pairs of jeans do you have? What is your favorite pair and why?

More about Paige


    1. thank you thank you for posting this! I, too, have recently been in search of the perfect pair of jeans. a friend had some that looked great on so I asked her about them. they were madewell’s high riser skinny skinny. she wears a 28 and I tried them on – perfect fit! so I ordered a black pair and dark blue pair from poshmark (the black pair will be a Christmas gift from my husband) in the high riser skinny (slim through the leg, not as skinny at the ankle as the skinny skinny). I just discovered that site and love that it allows me to search for favorite brands, but is an ethical way of purchasing. that and, as you mentioned in a recent post, cutting down on purchasing altogether. I’m so enjoying your blog!

      1. Taylor,
        I love Poshmark for finding more expensive brands more within my budget, but I also feel better buying secondhand when I can. I also buy myself things to be Christmas gifts from my husband 🙂 Are you new to Madewell jeans also? I’ve always heard good things, but I LOVE them!

        Thanks for your kind words as well,

    1. I am so fascinated and curious about doing a capsule wardrobe but also find it a little overwhelming on how to get started. Wasn’t it hard to purge your closet of so many things. I too have a closet full of clothes but struggle in the morning to put outfits together. I have stuff in the closet that doesn’t even leave the closet but I can’t seem to give them away because I might someday wear it. I really want to be more ethical and live a lot more simpler while being stylish and purge the excess that I have. Would love to hear how you started and kept from being overwhelmed.
      Thank you so much!!!

      1. Shellie,
        Your question totally inspired to start a new post going into more detail about my purging process as I think it’s one of the hardest parts. In terms of the ‘might wear them someday’ problem. Try to think of the occasion that you might want to wear that item for, and then look for another item in your wardrobe that would work for the same occasion, but that you would like to wear more. I have a few sweaters in a box in my basement that I just found that I was keeping because they could look cute around the holidays. Well, I have a few sweaters in my closet that I LOVE to wear and are just as cute (if not cuter), so it helped me find the ‘courage’ to let them go.

        Also, when I first started I packed a lot up and put it in our basement. Then, a few months later when I went back through, I found a lot of the items lost their appeal and I hadn’t missed them at all and that made it easier to let them go.

        I hope that helps, but I’ll share more soon!


    1. I usually tend towards skinny jeans because I’m petite and they just fit better without looking like I’m wearing too-big jeans (which is the epitome of the boyfriend look but on me it just looks sloppy). I used to have a pair of Banana Republic skinny jeans I’d had for maybe 5-6 years? So perfectly broken in and a dream to wear. Then on a trip last year I got a grease stain on them within 24 hours of a 5 day trip, and simply couldn’t save them. I felt like someone had cut off my hand (dramatic but you get it. Great jeans are hard to find.) Now I have 3-4 pairs all from different brands and not one of them truly fits like my BR jeans. I like the Everlane high waist but they are too cropped for me (who has long legs) in winter, my Levi’s are the best of the bunch, and I have a pair each from American Eagle and J Crew. The J Crew are a straight leg fit and have been in a consignment box. After 3 times of trying to get rid of them, I keep pulling them out and keeping them. I don’t know why as they don’t fit perfectly either. I think it’s mostly guilt over the price. I had 3 pairs of Nudie Jeans – organic, raw denim that cost a bloody fortune, but even after 6 months still hadn’t stretched to fit without cutting off oxygen supply (I was told they would stretch to a perfect fit and to buy them a bit tight…) I held on to them for over a year because I felt like leaving them in the closet vs chucking out the equivalent of $450 was smarter! I just brought in about 6 pairs of jeans to the consignment store, and have a few more waiting for spring. Finding the perfect jean is a never ending story!

      1. Andrea,
        My hope is that these jeans become like your Banana Republic jeans. What a bummer to have them ruined…especially as you try to find some that meet that expectation. I have heard a few people say the raw denim never really broke in the way they had hoped. I, too, felt like I was in a constant cycle of buying, trying, and selling to find the perfect jeans. Plus, postpartum weight changes also factored into a lot of turnover in my denim wardrobe. I still find myself browsing jeans and did just score a pair similar to this in a light wash on poshmark, but I’m going to work on contentment in my denim department and stop the cycle for a while (I hope)!!

        Thanks for sharing,

    1. Hi Paige! Do you mind sharing your Poshmark name? I was assigned a super long weird one… does that happen to everyone? We are about the same size and I would like to take a look at your “closet”.
      : )

      1. Hi Mariah,
        I think I was able to choose my name – it’s stylethislife over there too. My closet is pretty slim these days as this summer I packed up most of what was still listed and shipped it off to Thred Up because I wanted to clear it out of my house!

    1. Cute! I’m still in love with my Wedgies, and Christmas came early for my family, so I now have them in 3 colors! It feels a little weird to not have more “variety” in terms of fit/brand, but I guess I shouldn’t fix what isn’t broken.

      1. Lo,
        I just saw a pair of the Wedgies that had a regular hemmed edge and I was very tempted by them! Hey, if it’s working…especially in the denim department, go with it 🙂

    1. I have the hardest time with jeans! For the past 3-4 years, I have strictly worn Madewell high riser skinnys which have been amazing! I love the fit and the quality with most of the pairs I own (I still have the first pair I purchased and wear them weekly) – the new versions have “magic pockets” that hold you so you don’t have to worry about your midsection which is great feature. I recently wanted to branch out into other jean shapes and tried the perfect summer jeans. While I love the look of them, the 100% cotton is hard for me because I have muscular legs and a booty. I couldn’t even squeeze into my regular size and the size up fits well when first washed but stretch out to be unflattering. I also purchased the Everlane Modern boyfriends (black & mid blue) which I love but the aren’t perfect (I don’t like the extra fabric in crotch area on me, it bunches marking it weird when I tuck in tops..and the black pair stretches out in my knees). I purchased a pair of the Madewell Perfect Vintage jeans off Poshmark which are 100% cotton, first in 1 size up which was too snug and then 2, which first almost perfectly (just the slightest bit too big). They are pretty distressed so I can’t wear them to work but they have been great weekend jeans. I am loving the thicker weight/less stretch/non skinny denim but it is proving to be a challenge! I think a of people do find it hard to be content with denim because it is so tricky to get right and very personal…I am glad you finally found a pair that works well for you 🙂

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