Millennial thoughts on losing our cool factor, aka, straight leg jeans will not make me younger

This blog post is actually me styling straight leg jeans as a skinny jeans loving millennial because I have several pairs and am still getting used to them. But I love that millennials are suddenly talking about what Gen Z likes! I love it because I’ve been teaching Gen Z for a couple years now and I definitely can’t wholesale categorize them as people (duh) but I have noticed the style changes they bring to class! So today I’m reflecting on incorporating new trends while also staying true to what I like.

I think most millennials are joking when they’re freaking out online about Gen Z trends. But I also think…we’re sort of not joking! This whole “no more side parts” moment is kind of a rude awakening if you’re part of the generation that has called the trend shots within recent memory. We’re millennials! We killed Applebees, we are extremely vain, and we still don’t own houses, dammit, because WHEN WILL THIS ECONOMY GIVE US A BREAK. The least society could do is keep us cool but alas. We’re over or pushing 30 AND 40. We are out, baby.

That doesn’t mean I can’t try to be a little trendy, right? Like this outfit above. These are my beloved thrifted Levi’s. I found them at Goodwill for $6 when I was not at all looking for them. I get a little intimidated by them and have found that the best route to go to style them is to put them with tailored items, like this cashmere sweater and double breasted cardigan.

Similarly, I love wearing them with a blazer and pointed flats, plus a camel sweater. Would Gen Z reach for a blazer? They’re probably not that concerned yet about making mom jeans work appropriate, but I am committed to trying it. I basically swiped the inspo for this outfit from Anine Bing if you’re looking for similar looks!

For a more casual outfit I paired my straight leg black denim (also found secondhand) with a fun textured cardigan, my favorite ballet flats, and my free New Yorker tote (I think this entire sentence characterizes me as old lol).

I’m kind of at peace with being downgraded to the non-trendy generation, for the record, because the first thing you learn when teaching is that by being the teacher, you will never be cool again. You grade papers, no matter how much YouTube you show in class, you are a massive dork and students know it. A professor actually told me this on my first day of grad school and I found it pretty freeing. It’s a lot easier to enjoy yourself when you’re not worried about impressing others.

So I guess what I learned while putting these outfits together is that you can put on the mom jeans and have the middle part all you want, that doesn’t mean you’re ever gonna look like Gen Z. They’re amazing. They know how to browse TikTok (seriously I don’t get how to find the good videos). They look different than me because they’re 20 and no amount of trying to fit in with them will take the years back.

But I am enjoying changing my look up just a little bit! And some days it’s still fun to try to fit in with the youths…

I mean thank goodness space buns are back. Might as well embrace it with some tie dye and lace up boots 🙂

13 thoughts on “Millennial thoughts on losing our cool factor, aka, straight leg jeans will not make me younger”

  1. Ahh, this is so good. I love your reflections (and your thrifted levis!). It is weird being the ‘older generation’ now, and letting go of our ‘youngness.’ The teacher analogy is really interesting. I kind of feel the same things happens when you’re a mom of older kids. I mean, I have a middle schooler. There’s no way I’ll ever be the young, cool one in the family again. But that’s okay (I think). As for clothes, I think it was Stacy London who said don’t compete with the 20 year old because the 20 year old will always win. I do love my middle part and my baggy jeans, and so on, but I love them because I chose them and no one else chose them for me. I suppose I’ll just continue to wear what I love and if fear of coming across as old crops up (and it does) I’ll try not to give it any weight or priority in my mind. Thanks for the great post!!

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    1. It is SO weird. In my head I’m still 16. Like intimidated when I pass “cool” teenagers at the mall. I agree that we can’t fake being 20!!! And I’m trying to fall into my role gracefully as well 🙂

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  2. Half of my grad school class are technically Gen Z and it’s funny because the categorization really made them seem like aliens to me when they’re really just nice young people. But there definitely are (pop) cultural differences, and I have had a huge learning curve when it comes to slang and Tik Tok. I think I am starting to dress younger, too, but I’m just going with the flow. Still can’t help pointing out to them that I’ll be 33 this year if they start to say “our generation.”

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    1. I cannot believe Gen Z is in grad school?? Ahhh! Yeah some of the history they remember makes me feel old…a really random one is that they’ve always known climate change is a thing. Like they don’t remember An Inconvenient Truth coming out!

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  3. This is so funny!
    I’m a millennial too although born in ‘94, and I often feel like I don’t fit in with older millennials nor Gen Z! The first group tells me I’m too young to remember all the cool stuff (hello, I’m Russian, it takes 10 years for the cool stuff to arrive to us) and another group is like ‘wait you’ve already worked, graduated, married + all the cooking and having dogs? You’re not one of us.’ I feel cozy with millennials though because it’s fun to have things in common with people that are hitting their 40s. Gen Z is super weird to me. My sister is 16 and she’s an alien! Love your thrifted denim btw!!

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    1. Haha yeah my brother is on the cusp of millennial too and I think he only fits with it because he was the younger child? So influenced by what I was doing? I definitely think birth order plays a role. Omg I want all of your sister’s fashion opinions you should insta story them!!!

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  4. I really like that you both styled the “trendy” jeans and discussed how we as millennials won’t be “cool girls” any more. I have more to worry about than being dressed as the trendiest person and I am also not concerned with looking like I’m in my early 20s any more. Been there, done that, had a lot of fun but now I’m more comfortable with my style in my 30s than I’ve ever been.

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  5. LOVING those Levis. I also love this whole gen z millennial conflict…. I was born in 1980 and wore straight or wide leg denim all through high school and into my 20s. Uncool is how I’ve always been made to feel by millennials! Then again, I’ve never thought that good style and trendy are synonymous:)

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  6. Haha! I’m actually Gen X (I’m 42!) and just laughed when I started seeing all the pronouncements about side parts and skinny jeans. Because you know what? By now, I know what suits my body type, my face shape, my lifestyle, and I’m cool with what works for me. I look good in skinny jeans, and a side part is infinitely more flattering on my very very narrow face. But I still love reading fashion blogs and looking at Pinterest (OK I’m so old I never got into Instagram because I understand it can become a huge time-suck), and I am definitely interested in trying some wider jeans once it’s safe to thrift again.

    Your outfit with the orange tiedye tee, docs, and the bun looks amazing on you–and you’re rocking MY generation’s look from high school 😉

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