Full disclosure: the title is not in regard to yesterday’s conundrum. I’m a fast thinker but like not overnight fast. I didn’t figure out the thing about buying a size up or waiting out weight loss, but I did figure out why I don’t like the wide leg jean trend right now. That’s right, today I had a realization in the well-lit bathroom of a movie theater when my mom and I took Gemma to see Wonka. (It’s adorable by the way. Wonka and Migration — 10/10 must sees, especially for kids who get scared easily or are sensitive. These were easy movies for Gemma to watch!) So there I am in the warm glow of the Cinemark’s bathroom and I don’t know if it’s the nostalgia of a movie theatre or what, but as I saw my big pocket jeans of the wide leg variety in the reflection, it hit me: I look like I’m in junior high. Or at least I feel like it. The wide leg jeans with the loose tops and sneakers, that’s it! I’m in junior high again. But with sprouting white hairs and a mortgage, so I’m definitely not making friends this time around.

Do you guys remember JNCOs jeans? Iconic. Truly the 90s were a masterclass in iconography and we didn’t even know we were living it. However JNCO jeans were on the other side of JC Penney’s that we didn’t shop because it was the expensive side, which is the same as the Delia*s catalog — you can look but you can’t touch. So while I never had a pair of JNCOs, I longed for them, I so badly wanted to be a Delia*s girl. To be a catalog girl. For those who were, what was ordering from a catalog like and also did you get to ride in a limousine and/or have a water bed? What’s it like being so cool? Thank you for taking the time to answer these burning questions.

But today in my wide leg old navy jeans (that fit!) I thought wow you can barely see the tops of my sneakers…this is giving 90s cartoon character and I don’t know if it’s in a good way. I mean comfortable for sure, like I was curled up in that movie seat like it was my couch. But like…are we sure about this trend? Like collectively are we…are we okay with this? I feel like everything is SO oversized and while you’d think I’d embrace this while I’m not super confident in my body right now, but instead it feels like…I don’t know it is hard for me to wrap my head around. I mean, gosh should I just not fight this trend? Should I embrace it? Is my elder millennial showing? I’m just really struggling embracing these loose oversized trends. But I did have an epiphany — maybe that’s why I’ve felt in a rut. Because the trend right now is bigger pieces, oversized and loose, not tailored and perfected like I’m used to, so when I reach for pieces I’m used to I start to feel out of date. So…to oversize or to stay tailored? That’s definitely not a question for a Friday. That is definitely a Monday question.

So anyways, I figured the problem out.

PS: You can’t tell me this look from the side isn’t giving a Disney cartoon character from the 90s / 2000s. 

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Fit Details

I am in the medium of the sweater, it runs TTS for me. I am in the 10 of the jeans, runs slightly loose!

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21 Responses

  1. elder Millenial as well here. The only wide leg style that works for me is slightly cropped so the whole shoe shows. I can wear with tennis shoes for casual or heeled boots to dress up and I still feel cool, on trend, but not 13. I have the Mia High Rise Wide Leg from Joe’s Jeans and love them.

    1. I DO love the Mia’s, you’re so right. You gotta show the shoe! Everyone listen to Carly over here, she gets it!

    2. Thanks for the tip! I think the outfit looks great on you Kendi- feeling inspired to try a wide leg!

  2. Wider/baggy pants are one of those garments from My youth that I’m happy to see again. We didn’t have Delias where I grew up but I would still fantasy-shop there online back in the day. Finally accepted that they’re not for rainy days though, I spent so many years with damp hems! Silhouettes I am not so keen to see again include juicy couture tracksuits – did not think I’d see those again!

  3. This is my problem EXACTLY. I feel like a child again when I try to follow these trends, and then I feel out of fashion when I wear what I feel comfortable in…what to do…

  4. I’m a Gen-X and i don’t love the wide leg jeans because they just aren’t flattering on me. They look best with a slightly fitted top and i always want to hide my middle section. That’s why skinny jeans ans loose tops were my go-to (and still are). I’m wearing the wide leg jeans to be hip but they really aren’t for me!

    1. SAME. I find skinny jeans are just way more flattering but ya know my legs are my skinnier part. We are in the same boat, my friend.

  5. 36 year old here! I recently embraced the wide leg pant style and i am loving it! Same as you, it makes me feel like the cool teen that i was not. I feel a bit like an imposter? There are 20-something year olds whom i work with that have been rocking all our trends from the 90s/00s, and at first i wasn’t Feeling it, but now i’m just embracing it. I told my husband that i feel like the cool skater chick i never was- hahaha!

  6. Omg i forgot about delia’s. Those catalogs were my everything! And as someone who’s not comfortable in anything these days (42 and pregnant with twins wtf was i thinking), you look incredible. Truly. And ill forever be envious of your closet(s). Looking forward to buying from the new shop in a couple of months when i hopefully look less fluffy

    1. Twins, you brave soul. But I like to think of twins as a two for one deal, you know? You’re already pregnant so why not get two out of it? 😉

  7. We saw Wonka and Migration with our 7 yo over break and agree 10/10 recommend as well!!

    1. OMG Migration was just a nice goofy good time, wasn’t it? Gemma still does the Gwen ;pleaaasssseee’ thing lol

  8. This all makes total sense!! Please know we love all of your outfits and you always look fab. Thank you for sharing those old navy jeans— theyre the only thing that fits at the moment and i love them.

  9. I am also struggling with the loose and oversized trend. I am only 5 ft 3 in tall and most of the items overwhelm me (or make me look pregnant-which i most certainly am not). appreciate any outfit suggestions you have…

  10. Your 2024 posts have been nothing short of amazing. I love when honest, hilarious kendi comes out. I am all here for the delia’s catalog references. I’m only slightly sad that with a post called “I figured it out,” there wasn’t any mention of the summer sanders or Danny Tamberelli with what an iconic 90’s show that was. And…I mean, who didn’t gain a little extra poundage in 2023. You look as fabulous as ever.

    1. How did I forget Summer Sanders?! The original influencer, let’s be honest. I am here because of Summer.

  11. I remember getting the Delias catalog and never being able to order. My senior year my mom surprised me and ordered my prom dress from there. I think it was $125 which seemed like so much money when I’d always shopped the sale racks for my dresses. Now knowing what people spend on dresses that was so cheap.

    I also hear you on the wide leg jean trend. I got a pair, and I feel like a child when i wear them. But they are comfy. Like really comfy.

    1. YOUR PROM DRESS?! ARE YOU KIDDING ME? Wow. I aspire to be the Delia*S catalog mom.

      re: the jeans — so comfy. no wonder we wore them for years.

  12. I PINED over a tee in the Delia*s catalog that said “peas on earth” with peas holding hands around the globe. I’m 35 and while I think oversized is amazingly comfortable and wonder how I stuffed my legs into skinny jeans like sausages into casings for so long, I do think upper 30s and early 40s are a generally confusing time because we’re not young anymore but also not old and where is our place in the world?

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