Best Tupac Outfits of All Time: For the Cameras and Himself

• About
• Latest Posts

Josh Deleon

Josh grew up listening to all types of underground, mainstream, Hispanic, and all other parts of the hip-hop spectrum. Born at the end of the Golden Age of hip hop, the new wave and popularity of the scene helped shape his mind and personality. He has experienced the massive growth of the culture from the underground roots to the mainstream.

Latest posts by Josh Deleon (see all)

• Eminem and Tupacs Relationship: So Close Yet So Far - December 30, 2022
• Jay Z Gold Cologne Guide: One Business Too Many - December 23, 2022
• Pharoahe Monch Bio: An Underground King - December 17, 2022

The ’90s were a peculiar time, both musically and stylistically. Fashion trends of yesteryear stand out by today’s standards but perfectly encapsulates what it was like to be young and alive in those days. Skater. Grunge. Hip Hop. All styles that took over the last decade of the millennia, and Tupac was in the front of the charge.

The eponymous no shirt, bandana combo with saggy jeans look, and his “Thug Life” tattoo on full display are what we all see when we think of the legend. It’s an outfit that remains in pop culture just as his name does, but that’s not to say it is the best. Society has immortalized this vision of the gone-too-soon artist, but during his time with us, he took the chance to show the world what his wardrobe and creative mind had to offer.

As a fashion lover, I admire the man’s sense of style. When the trends kept coming and coming, Tupac managed to stay fresh and clean (except for one of these entries, but I’ll get to that). Throughout events, night outs, music videos, interviews, and award shows, the rapper was never one to hide his confidence when wearing something new. And I looked through it all.

So, there I was, researching Tupac’s fashion choices, and I started thinking about which one was the best. Now here we are.

Just for you, here’s my list of the ten best Tupac outfits of all time.

Bottom Line Up Front

For those who want number one right here—here you go. Everyone else should keep scrolling.

The best Tupac outfit of all time is a toss-up between the classic no-shirt, bandana look you see everywhere his name appears, and the post-apocalyptic outfit from California Love. Both are the best for many reasons, including popularity, style, vibe, and meaning. But since I choose the list, I’m going with California Love. It’s just cooler.

My Top Picks

These three outfits all share memorability and style with the late rapper. The most iconic outfits he ever wore and why we know whom to picture when we think of Tupac. These are his best in events and music video appearances, photo shoots, and his personal wardrobe:

California Love

Cosplay Difficulty: 7/10

Average Cost: $200 <

Key Features of the Outfit

• Bandana (black)
• Chainmail
• Boxing-like Glove (black)
• Leather Pants (black)
• Worn Under Shirt (black)
• Large Knee-High Boots (black)

It’s a look that stands out from all the others—and in a significant way. It’s more of a costume than anything; being from the viral music video for the song of the same name, this post-apocalyptic outfit dresses Tupac in a ravenous way.

He is tailored with chainmail drooping over his shoulders and protecting his torso, tall leather boots strapped high over his matching pants—a large glove on his left hand with a forearm guard to match. And finally, his classic black bandana tied around his forehead to keep himself in the look. It’s an outfit only worn once but is immortalized for all to remember.

Tupac in White

Cosplay Difficulty: 5/10

Average Cost: $100-$200

Key Features of the Outfit

• Wire-Frame Glasses
• Cross Necklace
• White T-Shirt
• Striped Flannel Jacket (white)
• Loose Pants (white)
• Gold Ring (left)
• Gold Watch (left)

This is one of my personal favorites, not going to lie. It’s the vibe it gives off. Almost biblical in a sense. In these photos, the artist looks to be reflecting on his thoughts, creating an atmosphere that feels almost profound. This is realized with the all-white outfit.

A large white and slightly gray flannel jacket laying over layers of bright white shirts helps with this effect. The glasses matching his heavy cross necklace and studded watch also play their parts in this poetic outfit. The stylistic off-white pants and that square-cut ring on his left hand make the pieces into one. Together, all of these make this look one of a kind. An outfit that captures the late artist’s insightful yet fashionable ways.

Tupac Shakur

Cosplay Difficulty: 2/10

Average Cost: $20-$100

Key Features of the Outfit

• Bandana (blue, black, white)
• Cross Necklace (silver)
• Boxer Briefs (any color)
• Large Jean Pants (blue)

So iconic that some of us recreated it as a hologram for a posthumous performance back in 2012 at Coachella; this look will live on forever. There’s the signature bandana on his head, the cross-chain necklace around his neck, his “Thug Life” tattoo on full display, and the saggy jeans to wrap it all up.

It’s what many people picture when describing Tupac for a good reason. Because of its easy and stylish manner, the look is the most common in his wardrobe. Often performing live shows in the outfit, this one has to fall in one of the top spots.

Selection Criteria

While those three are my personal favorite outfits from the rapper, there’s still a lot to look forward to; so before we get into the good part, let me break this down for you. I chose these specific outfits based on their popularity, appearance, vibe, and what they meant (if anything) to Tupac when he wore them.

The man was a genius—you know, he put careful thought into these looks. And depending on where he would wear these outfits, the style would change. This is why I also divided the outfits between his event appearances, photoshoots, and everyday wear. They’re ranked as well for the fun of it. Below are the selection criteria:

• Must have memorability or be deemed worthy of being called ‘iconic.’
• The look and how much drip Tupac had in these outfits.
• The vibe the man gives off when wearing a specific set.
• The look’s meaning and what it may stand for.

And with that, let’s get started.

Event Appearances

This first category is Tupac’s public appearances. These include award ceremonies, music videos, movies, etc. These outfits were meant to be seen by millions and can be harder to replicate.

Bonus – First Annual Minority Picture Awards

Cosplay Difficulty: 4/10

Average Cost: $100-$200

Key Features of the Outfit

• Snapback Hat (gray)
• Striped Long-Sleeve Polo Shirt (white/navy blue/teal)
• Overalls (blue)

It’s not officially a part of the ranking here, but it is still great and one of my favorite public looks from him. So, let’s start right and bring this striped look front and center. Almost child-inspired, the blue overalls are only the final touch as they cover over the long sleeve. With a white base with dark blue lines running horizontally, the middle of the shirt fills in a few white gaps with more teal-shaded ones. These two go well with the corresponding-colored backward hat.

The overalls would become pretty popular in the decade, and Tupac helped with that. This outfit’s popularity, style, and vibe rank high here.

10^th Annual Soul Train Awards

Cosplay Difficulty: 5/10

Average Cost: $90 – $150

Key Features of the Outfit

• Beret (black)
• Camouflage Jacket
• Camouflage Pants
• Fingerless Gloves (black)

Tupac wore pretty standard camouflage in his time, which may be the most remembered outfit of this style. Receiving the Best Rap Album award for his third album, Me Against the World, the night would be most remembered for this look.

The MTV Video Music Awards

Tupac at MTV Awards (1996)

Cosplay Difficulty: 7/10

Average Cost: $200<

Key Features of the Outfit

• Suit (gray)
• Patterned Vest (green/yellow)
• Large Medallion (gold)
• Pipe (brown)

That large gold medallion blinds you right at the center—and it works! The stunning grey suit combo worn here in 1996 didn’t quite make the top ten, but it is excellent all the same.

Poetic Justice Premiere

Cosplay Difficulty: 8/10

Average Cost: $150 <

Key Features of the Outfit

• Beret (black)
• Karl Kani Shirt (black)(alternatives available)
• Large Karl Kani Button Coat (white)(alternatives available)
• Pants (white)

This one may be nearly impossible to replicate exactly, but I still enjoy the look.

After receiving praise for his role in the 1992 film Juice, the rapper/actor would star in a movie alongside Janet Jackson. This new film, Poetic Justice, finds Tupac in a romantic drama where he would further prove that he is more than just a rapper. And at the world premiere, he’d also make another fashion statement.

So, this outfit. It’s the bright denim overcoat for me. That seals the deal. Then there’s that solid, thick, gold chain shining around his neck. The black shirt underneath represents his friend and designer, Karl Kani, and matches a similar hat to the one worn at Club Amazon. Then there are the matching bright pants to finish the set.

Walking into his second movie premiere, Tupac was nearing peak confidence levels, and his clothing choices were starting to reflect his wealth and status in the mid-’90s.

So, those are the best outfits from Tupac’s different appearances, but how about the outfits not meant for the paparazzi to make public? While many of his event outfits were chosen for a larger audience to witness life, the photo shoots throughout his career paint another story for the rapper.

Photo Shoots

Whether wanting to study the fashion Tupac brought to the nineties or are feeling inspired to dress like the legend; his photo shoot works can be a great place to look.

Thug Life Overalls

Cosplay Difficulty: 4/10

Average Cost: $100

Key Features of the Outfit

• Striped Beanie (white/black)
• Hoodie (dark blue)
• Custom Overalls with “THUG LIFE” on the stomach (blue/white)

This simple, workwear-inspired outfit marks the overall first appearance on this list, and paired with the dark hoodie and striped beanie, the ‘Thug Life’ written at the stomach is made for Tupac.

Death Row Look

Cosplay Difficulty: 5/10

Average Cost: $180-$250

Key Features of the Outfit

• Bandana (black)
• Pendant Chain (gold)
• T-Shirt (white)
• Jeans (blue)
• Silver ring (left pinky finger)
• Bracelet (left)

This look falls on this list primarily for its popularity and iconic status in Tupac’s history. The whole straps thing and waist-only design aren’t quite it for me. We’ll come later to some perfect ones further on the list, but I can’t deny the memorability of this look.

A bandana is worn with the look, showing the tied end forward. A gold chain rests over a solid white T-Shirt while the signature leather vest compresses his torso like a corset. A bracelet and ring displayed along with the west side symbol end the photograph at that.

Leather Vest

Photograph showing iconic look

Cosplay Difficulty: 6/10

Average Cost: $150-$300

Key Features of the Outfit

• Bandana (black)
• Chain (gold)
• Leather Vest (black)
• Jewelry Accessories (gold)
• Leather Jeans (black)

Another look commonly associated with the rapper; is the iconic black leather vest steals the attention here. A solid gold change hangs around his neck, matching the jewelry around his wrists and hands. Similar to what he’s wearing on his famous “All Eyes On Me” album cover (although more easily visible), he commonly wore it shirtless. While I can only imagine how that would feel all day, this style can be seen in the hip-hop legend in interviews, publication images, and other places.

This image of the outfit here is one of its best. The black bandana and the unamused glance to the side hint at the personality behind the frame, reminding us just whom we’re dealing with. There are other renditions with slightly different styles, which I’ll get to later on, but this one still gives off the unique vibes of Tupac.

When it came to style, Tupac knew when to dress accordingly. The mass audience for his event outfits and the publicized prints of his photo shoots kept his fashion sense in those moments, but the looks to come are just the man choosing to dress how he wants, no matter the location.

Everyday Wear

From nights out in the club to rehearsals backstage, these more casual looks show the diversity the individual had to give. Much like other outfits listed already, some parts may be harder to get than others if you’re looking for an outfit to dress in, and the costs may vary depending on where you get them from. Still, many casual outfits can be replicated with more affordable options.

Rehearsing

Cosplay Difficulty: 8/10

Average Cost: $200 <

Key Features of the Outfit

• Velour Shirt (peach)
• Pants (white)
• Jewelry Accessories (gold)

The man was blessed in many ways, and his appearance and fashion tastes were among those gifts. On another rehearsal for a show, Tupac decided to flex his drip and come out wearing this Velour top. The sheen and reflections from the piece are enough to catch your eye, but as he nonchalantly adjusts his ring, showing off the rest of his jewelry in the process, you can see the power he knew he had.

This look leans more into his appearance as the slim fit of it all, along with the light colors, portray the more luxurious side of Tupac’s personality. Note the absence of his signature bandana. More on that later.

Club USA in New York

Cosplay Difficulty: 6/10

Average Cost: $100-$150

Key Features of the Outfit

• Bandana (blue)
• Under Shirt (white)
• Button Down Shirt (light)
• Leather Vest (brown)
• Jeans (blue)

A few changes in this curious outfit; his leather vest is now a visible brown fitted close to the loose button-down shirt. While there is a white undershirt and a blue bandana to accessorize a bit more, the blue jeans make the look feel somewhat thrown together, hoping it would work. And I say it did.

Despite the seemingly random articles of clothing being thrown together here, they all blend just fine. Not many people would be able to pull outfits like this, but thanks to his energy and complementary features, this one works for the rapper.

Club Amazon

Cosplay Difficulty: 5/10

Average Cost: $80-$140

Key Features of the Outfit

• Beret (black)
• T-Shirt (white)
• Leather Vest (black)
• Jeans (dark)

A night that would capture more than one rare photograph of these legends together, my fifth entry was that of Club Amazon back in 1993. Wearing a blend of everything in his style wardrobe, Pac is seen starting with a sizeable white T-Shirt. Resting over, this is one of the rapper’s famous leather vests like the one discussed earlier. Now, instead of the traditionally tied bandana, he’s sporting a black beret in its place. The monochrome look must have looked worked wonders that night.

Tupac stands with a young Nas and Redman here, but other photos also show Biggie side by side. As a whole, the moment’s memorability gives this outfit a timeless stamp. Someone can put this together today and still look as good as ever. One of his more casual looks, the Club Amazon outfit deserves its spot on this list.

Frequently Asked Questions

Final Thoughts

Beyond this short list of the best Tupac outfits of all time, there are dozens more that I couldn’t go over here. The man just had style, and he enjoyed showing it. But when it comes down to which one reigns above the others, then to me, the answer becomes much clearer as only one stands above the rest. And it’s the ‘California Love’ one, by the way, if you’re skipping to the bottom.

It stands out far more than anything else he has worn; it’s what he wears in one of his most iconic music videos, Dr. Dre is rocking his own apocalyptic outfit with him, and it looks cool. The costume fits in with the meaning of the song and the sequences around him, and he still wears his legendary bandana as well. These facts and opinions build a solid case for why this is the best of his outfits.

Although many people would say it’s the “Thug Life” classic that should be number one, I can see that too. And it almost was! It hits all the same criteria, but in a way, you could easily do it at home yourself. Either of these could work as number one, and the rest is up to you.

Work Citation

• “7 of Tupac’s Most Iconic Outfits” by Kendall, Zoë, i.D. Vice, June 16^th, 2021
• “Nas + 2Pac + Redman + B.I.G. at Club Amazon (1993)” by DJ Save One, Hip-Hop Nostalgia, August 22^nd, 2020
• “Tupac Shakur’s 21 Tattoos & Their Meanings” by Body Art Guru
• “17 Top Tupac Style Moments” by Haveford, Christine, Scubby
• “We Need to Talk About Tupac” by Okwodu, Janelle, Vogue, June 16^th, 2016
• “For The Record: The “Thug Life” Awakening Of 2Pac’s ‘All Eyez On Me’ At 25″ by Ketchum III, William E., Grammy, March 29th, 2021

Looking for more interesting readings? Check out:

• Best Tupac Bandanas Guide
• Best Tupac Socks Guide
• Best Tupac Hoodies Guide: Which Should You Buy?