Solving The Skinny Jeans Conundrum

Apr 11, 2024

Depending on who you ask, Gen Z has cancelled skinny jeans or perhaps they are back? Trends change, and we should change with them. But what do you do when you have a closet full of skinny jeans in a wide leg world?

Edit, Don’t Purge // Go to your closet. Take out all of your jeans. First, separate out the ones that don’t fit. Life is too short to wear clothes that sag or pinch. If you’re not willing to pay for tailoring, you need to free yourself of ill-fitting denim through sale or donation.

Second, pull out the pairs you don’t love. If you haven’t worn them in six months, if they’re not your favorite, it’s time to find them a new home. It doesn’t matter what you spent on them. You’re building a wardrobe, not curating a museum. If they’re not being worn, they have to go.

Third, find the skinny pairs you really love and wear. These ones you can keep. In my own wardrobe, I am keeping a much loved pair of light wash skinny jeans, a white ankle pair, and a black pair. I wear all three. I’m comfortable in all three. I look good in all three. It won’t bother me that they’re “out of style.”

Read Up on Styles // My body has changed. Your body has changed. And you need to find the right style for your body now. In a perfect world, we’d all hire a personal stylist to help. In the real world, most of us will need to do our own research.

The first thing you need to do is to take your measurements. The Tailorette has a great video that explains how to take your own measurements. You just need a soft tape measurer and a mirror.

Next, Who What Wear explains how to use those measurements to figure out your body type. I am a pear. Always have been, always will be. But these days, my body is more of a Bartlett than a Concorde.

When starting to look for jeans, Nordstrom has a basic fit guide that you should read as a first step. Stitch Fix has one that is a bit more in-depth if you need that. And if you like videos, this one is really helpful. Here are the time stamps for the different shapes: 4:11 – Rectangle 9:11 – Pear 12:52 – Inverted Triangle 16:33 – Hourglass 18:28 – Apple.

Once you know what styles are best for you (for me, it’s trouser jeans and flares with a shoe that has a slight heel), you can go shopping.

Don’t Get Discouraged // Trying on jeans can be fun. You just have to accept that 90% of what you try on, you won’t like. That’s just reality. Last month, I tried on a flared style that I would have loved at 30 to find that they made me look weirdly disproportionate. It happens. Just remember: It’s not you, it’s the jeans.

My best advice is to go to Nordstrom or another large department store. Tell the clerk that you’re shopping for some new styles — wide leg, trouser, flare — and that you wear size X in (insert brand here). Then, tell her that you would like to take 10 pair into the dressing room. Lastly, ask for a little privacy so that you can try them on. Nothing is more annoying than when you’re trying on jeans and the clerk keeps asking if they can help. I don’t know, can you make me 25 again?!!?

Hate doing things alone? Make a personal styling appointment or take a friend. The point is to make the situation comfortable for you. Just make sure that if you’re going to go shopping and have lunch that you eat after you shop. Salt, alcohol, a big meal, all of those can make this process tougher.

Need to order several pairs online instead? I recommend ordering 6 pair at a time. First, order three different styles, two pairs each. A good place to start would be two flare, two straight or bootcut, two wide leg. For the wide leg, I would order one ankle length pair and one full. Same for the flare. If you’re not sure which rise will look best, vary those as well. Then, get half-an-hour to just stand in front of the mirror and try them on. Remember you can find most styles in a different wash if you like the look but not the color. And then, just pack up the ones that don’t work and ship them back.

See This as a Chance to Start Over // Your goal is to rebuild a new collection of jeans, but the right jeans. The jeans that make you feel good. The jeans that make you feel cool. If you try on 10-12 pair, you’ll probably find one or two that you love. That’s a good ratio.

Don’t keep a single pair you feel ‘meh’ about it. The most you’re ever going to like something is the first few times you wear it. So if you don’t love it then, you never will. You deserve clothes that make you feel good.

If at First You Don’t Succeed // I have tried on 10-15 pairs of jeans since November.  I’ve bought two styles: these and these. That’s it.  And while I love the ones I bought, I’m still searching for my white whale.  It happens that way sometimes.

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  1. Chelsea says:

    Oh how I love a great how-to list full of resources! Thanks for the in-depth advice on such a daunting task.

  2. Jules says:

    “You’re building a wardrobe, not curating a museum. If they’re not being worn, they have to go.” 🤣 words to live by

  3. Jess says:

    Love the “meh” comment. That’s been the driving force behind my clothing purchases for at least the last year. If it’s not an immediate strong response for the good, then it’s a no. No “mehs” allowed.

  4. Kelly says:

    I’ve been on the jeans hunt, and it’s been mostly disappointing. I did love an Abercrombie pair, but after washing and wearing they bagged out on me. I’m now reconsidering the stack I had planned to return to Everlane.

  5. A says:

    Highly recommend getting jeans fitted to you at Madewell. I wanted nice black jeans that I could wear to the office, and their stylists pulled different styles in different sizes based on the fit I was going for and material. They do free hemming if you need it, too. You can also order a bunch of styles and have them shipped to the Madewell store near you for a fitting session.

  6. Hannah says:

    Thank you for this!

    I am also a pear. Are Paige jeans all generally good for pears, or do you suggest sticking to those particular styles? Always looking for new pear-friendly jeans!! 🙂

  7. Diane says:

    I have a pair of wide leg raw hem ankle jeans like the Paige ones you have and am struggling to put together outfits that don’t look top-heavy and shapeless. I would love to see how you’re wearing wide-leg crops and get some ideas!

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