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side note by an indigo day · Jul 22, 2026

Millennial Style Academy Vol. 6 // What We're Doing With Our Denim Jackets

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Your security blanket denim jacket needs a slight refresh, and you'll be glad you swapped

The Gerard Darel Denim Jacket I Reach For The Most

What was once my go-to topper for any and all outfits has been collecting dust for almost three years now. I’ve toyed with donating my beloved denim jackets, but it’s the Millennial in me who thinks it’s just a phase we’re in—they may come back. Or I may really want to reach for one at some point.

But in all honesty? I haven’t thought about them in almost three years.

I moved to NYC in 2023, and it’s been a really good gauge to see which pieces I reach for and haven’t even thought about. Which should permit me to finally donate the denim jacket. I haven’t. Yet.

What I have done, though, is reach for new styles of denim jackets, or totally different jacket styles altogether. I see this question so much in my DMs and across social media. Millennials are asking, "What are we doing with our denim jackets?” And I’m here to answer that, along with a better alternative.

The Millennial Style Academy is in session, and today’s topic is: denim jackets.

Side Note is for millennial women who want to feel a little more put-together. Support my work and become a free or paid subscriber.

The Verdict On The Classic Denim Jacket

Listen, it’s not a bad piece. At all. But it is feeling very dated and lazy in my opinion. It’s been around for ages. And while we started with shrunken ones, then moved to oversized, and then into cropped and boxy, it’s been a style that’s evolving for the last 20 years. I think it’s kinda run its course for now.

That classic denim jacket style, like the ones featured above, no matter the shape or style, feels a bit dated now. And there are really easy swaps to make that will not only make you feel less dated, but actually elevate your look and make it feel not so casual. And also allow you to probably get more use out of it.

Shop the jackets →

SHOP DENIM JACKETS

Option 1: A Different Style of Denim Jacket

If you still love denim as a layer, update the silhouette, not the material. My go-to right now: slightly oversized, slightly cropped—not swinging too far in either direction.

Beyond that classic shape, there’s a lot to choose from too.

  • Chore jackets — cropped or longer

  • Bomber jackets — casual but current

  • Collarless “lady” jackets — more polished and preppy

  • Denim trench coats — long or short

A few favorites from the above roundup include the Soeur one that’s screaming "cool fashion girl," or this dark-wash bomber jacket from Pilcro. You can shop these and more favorites here →

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My favorite non-denim jackets that will go with much of your closet. Shop them all →

Option 2: A Totally Different Jacket Altogether

Each of these does what the denim jacket used to do. Bridging casual and put-together, but with a more current sensibility. While denim is a favorite fabric of mine, it does typically read very casual, especially in the classic denim jacket silhouette. So reaching for something not only in a different fabric, but in style, can really elevate your look while still keeping things casual and put-together if you need it to.

  • Cropped trench — the most elevated and easiest swap. Works for spring and fall too.

  • Bomber jacket — still casual, but feels fresh. Great in nylon or satin. Go oversized for a cooler, edgier look, or more fitted when balancing out volume on the bottom.

  • Leather jacket (or vegan leather) — it elevates everything the denim jacket used to. Go for a bomber or slightly oversized and boxy fit.

  • Blazer — structured and cool. Go oversized for a cooler, more on-trend look. Works for any season based on the fabric you choose.

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  • Chore jacket — this is the closest to a denim jacket style if you need a simple update. Try a shorter one to make it easier to style.

  • Lady jacket — the most polished and preppy option. The “grown-up” denim jacket replacement for the girls who lean more feminine and preppy.

  • Cardigan - we seemed to have forgotten that a cute little cardigan is a great jacket alternative. Maybe it’s because many Millennials are holding onto those long knee-length cardigans. I’m talking more 90’s inspired, fitted cardigan that hits at the hip like this. A perfect sweet addition to an outfit.

Side Note - some of my favorite affordable lightweight jackets to shop over on an indigo day >

My favorite non-denim jacket alternatives in my closet.

What I Did & My Top Picks

I have found myself reaching for a handful of denim jacket alternatives, both in denim fabric, and non-denim. The above are a few of my favorites. From a cropped chore jacket, to my go-to oversized blazers, and the cropped trench, these are the ones I find replacing my denim jacket for the last two years with ease.

The Denim Jacket Itself: Keep, Donate, or Hold?

I’m torn on this myself, so I’m curious what you’re doing with yours. I may be keeping just two. My cropped slightly boxy one, and my super oversized one. I wore them the most. But any others that are in between, I think I’m donating.

What will you be doing with your denim jacket? And have you found a good alternative you reach for more?


If this made you rethink your denim jacket situation, forward it to a friend who needs the nudge. And if you've got a denim jacket you're obsessed with right now, tell me about it in the comments.

Read on anindigoday.substack.com

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