Weird But Legal Fashion Idea: Copy Outfits Leonardo DiCaprio Wore in the 90s

Do you ever feel like you’re stuck in a fashion rut? *turns around in chair to face camera from the other side* I’ve been there.

Okay, that’s enough of that, but really, do you? And really, I have been there. I’m there constantly. I’ll do this thing where I’ll catch myself wearing the same outfit in the exact same way and it makes me feel dead inside. I couldn’t change, like, one thing about the entire situation? We’re keeping the socks the same, too? Tragic.

When this happens people are quick to suggest looking at fashion blogs or magazines. Honestly? They’re fine. I’ll look at them, sure. But after enough pictures, it all feels too polished and in general they all seem seem to wonder if you’ve just considered looking rich and beautiful? Or they suggest going shopping! Spice up your wardrobe. Get out there and spend some cash, girl, you deserve it. Except, no, I don’t, and do any of us, really?

Of course I want to be a person that’s nonstop crushing it in a rotating lineup of perfectly tailored off-shoulder jumpsuits. Absolutely I do. That’s a fact. I’d love nothing more than to enter a peak Anna Nicole era of my life. But until somebody gives me the zero-questions-asked $10,000 that I’m entertaining as a real possibility in my life, that’s not going to happen.

I need some realistic solutions for something that’s not actually a problem. Which is why I went a little off script to break from routine. Just for fun. Privately. Shhh, it’s just for me. Until now:

Copy outfits Leonardo DiCaprio wore in the 90s.

Hear me out.

1) This is totally legal. Check the books, buddy.

2)  We’re working on solid ground. Decade-hopping to rip styles is straight out of the Professional Fashion Editor handbook. Recycled trends aren’t coincidences! Anna Wintour 100% has a Rolodex filled with the fanciest jean cuts from every decade just in case she’s ever low on content.

3) This is a chance to let your brain reset, like a writing prompt but for clothes. For people coming from a women’s fashion perspective like I am, this is a chance to explore how men’s fashion approaches color combinations, patterns, layering, and textures, warping your brain around them, and then updating them as you see fit. For people not coming from a women’s fashion perspective, these are still good outfits to mimic. The collar placements alone on some of these things are enough to change your whole world around.

4) Dressing as Leonardo DiCaprio is a meta gay experience. Who was many a baby queers crush if not Leo f’in DiCaprio, his assessable, pretty face speaking to hidden sensibilities?

5) This is the best part: you get to have a secret while you walk around in public, and not a bad one, like you got a puppy from an adoption agency but then returned it in the middle of the night so they’d find it in the morning. I didn’t do this! I’m just saying it’s not that kind of secret. Relax! The secret you have is that you essentially get to prank every single person you encounter. The check out lady has no idea you’re dressed as Leonardo DiCaprio from the 90s and yet there you are. If anything this one’s going to get you out of the house.

Enough talking, let’s get to the goods.

Black bomber jacket, brown polo shirt, gray pants, white soled shoes. Love it, love it all, love the color scheme, love that this headband is making an appearance. Those appear to be corduroy pants and let me just say if I had a pair of high rise corduroy pants in gray I’d probably ascend to a new level of inner peace, wherever Owen Wilson resides. If you don’t have a bomber jacket, improvise with something puffy and/or oversized. Life’s right there for the taking.

Okay, yes on the monochrome blazer and high cut shirt combination. Make the pant the same color, slick your hair back and slip into the night. Close your bank accounts, take your cash, and get in a car. Drive until you hit a spot that has mountains and water.

My man Leo looks high as hell here, but that doesn’t mean he doesn’t have a point with matching his lenses to his shirt. The button up shirt appears to have a polyester sheen to it, which under a blazer is a risky gamble to make in the ventilation department, but what is fashion if not taking risks. Bottom line here: mix and match navy and brown like you’ve never mixed and matched navy and brown before.

This burgundy leather jacket, brick red shirt, and patterned pant of a similar hue must be recreated en masse. Oh god, and the Sambas. Does anyone have Sambas still?!? If you don’t have access to a burgundy leather jacket, as I believe those were all sucked into some sort of portal during Y2K, what about a rain slicker or an enthusiastic cardigan?

Dark demin, some athleisure shoes, and a whatever shade of tan that shirt is is a cartoon Italian chef kissing his fingers. Mwah. Beautiful. I’d go for a tuck of the shirt but that’s just me. No disrespect, obviously. I’m not the one who’s dated a thousand supermodels, what do I know?

Making a white undershirt the star and not the supporting role of an outfit and then pairing it with grays and browns is powerful and I think you should try it.


You were made for a fitted tee with the same color wide leg pant and white socks with shiny flats. Make the pants a long wide skirt if you want!!

This is for fun, why not try it? Or if you don’t want to try it why not just enjoy some pictures of Leonardo DiCaprio, but from the 90s. Where’s the harm? The earth is literally melting ;)

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Los Angeles based writer. Let's keep it clean out there!

Erin has written 208 articles for us.


  1. When i was six years old, I wanted his haircut so badly. Like I had a go with a razor in the bathroom myself kind of level. I think growing up and stealing his fashion choices is a great progression for me to take in life.

  2. my day was at a -5 before i read this and now it’s at a +25

    this was the first time i lol’ed, followed by many more:
    “after enough pictures, it all feels too polished and in general they all seem seem to wonder if you’ve just considered looking rich and beautiful?”

  3. The only time I ever successfully copied a style was right after high school, when I had a Molly Ringwald phase. But this almost seems doable. And it’s definitely a lot of fun to mimic a style no one has any idea you’re mimicking. Secret dress-up games, wohoo!

  4. I think those sneakers were actually Gazelles, maybe? And those are my preferred non-dress shoes. I wear them every day. :)

  5. I think those sneakers were actually Gazelles, maybe? (as opposed to Sambas) And those are my preferred non-dress shoes. I wear them every day. :)

    • They have both classic Sambas and Gazelles at – although I have to check if we’re allowed to shop at I vaguely recall something about them supporting Trump.

      • I did find the Samba’s on Adidas’ site, but sadly it was in kids sizes, which is great news for some.

  6. The secret you have is that you essentially get to prank every single person you encounter.

    This is literally my fashion goal every day. If I don’t walk around having an in-joke with myself about something I’m wearing, I’ve had a bad morning.

    • I had a sparkle gold glitter headband on straight from the little girls section at target today accompanied by a pretty butch look for everything else; Unspeakably long leg hair (truly chewbacca inspired) and baggy cargos with a black tee (for work) and I just giggled all day as straight girl after straight girl wondered what kind of crazy I had for breakfast–inside fashion jokes make me laugh and laugh–viva la resistance!

  7. Can we also do this for late 90s Taylor Hanson? He was my first crush and style icon. Also, why did no one notice that I was always obsessed with boys that looked like girls and suggest I might be majorly gay?

  8. Where do I apply for the zero-questions-asked $10,000 ? Wait, did I just miss out on it because I asked questions?

  9. Leo looks high in 60% of these pictures.
    Also also also I had the exact same pants from that picture of him with David Blaine and Elijah Wood

  10. This article gives me succor in a time of need. It should be planted in the air conditioning systems of all office blocks and public buildings, so that it may become a gentle breeze to salve the wounds the Western world inflicts upon itself.

  11. Was just about to do this w some other celebs (actually been doing it and only not name dropping cos it won’t mean anything to most on here) but tempted by Leo now. Esp the matching shades to shirt thing. I have to wear dark glasses cos I have light sensitivity so it’s great to be able to turn it into a fashion thing too.

  12. Yep. I graduated high school in 97. This is weirding me out. I had a lot of similar clothes at the time. Now, I wear primarily black and you know what? I don’t feel in a rut, because my whole wardrobe is a rut. I’m cool with it.

  13. Pretty sure in middle school I wore a version of that bead necklace that’s in two pictures toward the end. And I probably made it myself? That and lots of hemp chokers.

  14. I am wearing black Adidas with white stripes and soles right this very second and I did not know when I bought them that they were part of my path to FULFILLING MY DESTINY but here we are.

  15. I need all of these outfits. I never have the patience to find my size in thrift stores so the oversize stuff is *perfect*. You’re a genius.

  16. “Dressing as Leonardo DiCaprio is a meta gay experience. Who was many a baby queers crush if not Leo f’in DiCaprio, his assessable, pretty face speaking to hidden sensibilities?”

    Ha! When asked about my favourite lesbian movie I always answer: “Titanic.”

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