Top 15 Chicago Retro jerseys to own for this summer

No matter who you are, or what your wardrobe looks like, if you’re a Chicago sports fan having a few retro jerseys in your collection is a must.

Summer is the perfect time to rock these sweet throwbacks with the weather being nice out. You can rock them pretty much anywhere. Whether you’re at the beach, walking around the city or even at a sporting event, you can’t go wrong.

Wear the right one and you might even get a compliment from a fellow sports fan. Check out our list of the best ones to wear this summer.


Any player that played less than 3 months with a Chicago team.

This is for the Jimmer Fredette’s, the Manny Ramirez’s, the Ken Griffey Jr.’s of the world – God the White Sox had a lot of trades for over the hill guys. If you can find a really obscure jersey, go for it by all means.

My personal favorite is a Michael Jordan White Sox jersey, simply because of how the GOAT from one sport was terribly human in another

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15. Elton Brand Chicago Bulls jersey 

elton-brand-chicago-bearsOne of the first picks post-Jordan era, Elton Brand was actually really underrated as a Bull, posting back to back seasons with at least 18.5 points and 9 rebounds per game.

It didn’t matter though, because the Bulls were terrible, so some could argue Brand was putting up empty stats. Brand was traded to the Clippers so that the Bulls could draft Eddy Curry and Tyson Chandler in the same draft, which really marked the down spiral of the franchise.

Brand’s Bulls jersey is pretty hard to find, so if you do get a chance to grab it, it’s a must own.

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14. Bobby Hull Blackhawks jersey


I know that Bobby Hull is a legend, and that he’s one of the select few to have his number retired by the Blackhawks. He was a huge reason Chicago is a hockey city and probably the biggest reason the Hawks won the Cup in 1961.

But I can’t move him down the list any further because I really can’t justify wearing a hockey jersey in the middle of summer.

If it’s one of those high 60-low 70 degree days with a breeze? Okay, sure, go for it. But anything past 75 and you’ve lost me. Wear with caution.

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13. Sammy Sosa Cubs jersey


Sammy Sosa was beloved right up until he was caught putting cork in his bat.

That doesn’t necessarily negate everything he did in a Cubs uniform – at least in my eyes. Sosa was one of the most explosive power hitters in the early to mid 2000’s and his two hop routine following a home run was a joy to watch.

Wearing Sosa’s jersey is a nice throwback to the early Cubs, who weren’t quite as dominant nor as fun to watch as the current day version, but still a fun bunch nevertheless.

Now if only the team would bring him back to celebrate the years Slammin’ Sammy was hitting baseballs over the bleachers at Wrigley Field.

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12. Horace Grant jersey


Horace Grant was a big part of the first Chicago Bulls three peat.

He had a solid midrange shot, good defense and he crashed the boards really well. Though he left because he wanted more shots elsewhere and eventually went on to win another championship with the Los Angeles Lakers, Grant’s contributions as a Bull cannot be overlooked.

Beware: if you get his jersey, you have to find the matching goggles. Kidding…kinda.

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11. Bo Jackson White Sox jersey


Bo Jackson had his best moments as a member of the Oakland/LA Raiders and as a Kansas City Royal.

That’s how he’s usually remembered anyways.

Jackson may have had his most memorable moment as a member of the White Sox, however. In his very first professional game back from a dislocated hip, in his first at bat, Jackson hit a home run.

While there were only flashes of greatness following, bringing out his jersey and giving a quick history lesson to the younger generation is well deserved.

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10. Devin Hester Bears jersey


It may seem like an odd choice at first – given that it wasn’t too long ago that Hester was playing for the Bears and that he’s still in the league – but Devin Hester was THE man.

The greatest returner in the history of football once called the Wind City home and was universally beloved here, so it makes sense to wear the jersey and bring back some of the good vibes.

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9. Any White Sox 1983 jersey 

Chicago White Sox starter Chris Sale delivers a pitch against the Seattle Mariners during the first inning of an MLB baseball game in Chicago Sunday, April 7, 2013. (AP Photo/Paul Beaty)

I love this look for the White Sox and I love that they wear these every home Sunday game. Frankly, you can’t go wrong with whose jersey you wear, whether it’s Harold Baines, Ozzie Guillen, Carlton Fisk or whomever.

With this jersey, you will truly be appreciated by the die-hard fans on the South Side or even someone who just loves baseball. So go and get one, like now.

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8. Ron Santo/Ryne Sandberg Cubs jersey


You can’t go wrong with rocking either former Cubs infielder jersey. Santo held down the hot corner throughout his entire career with the Cubs and was finally inducted into the Hall of Fame.

Sandberg was just marvelous at second baseman and made the flashy plays we all love to see. He is also in the Hall of Fame.

Bonus points if you can find older versions of the jerseys and not the standard home or away versions.

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7. Mike Singletary Bears jersey


Singletary was one of the most important pieces to the ’85 Bears defense, which might be the greatest defense ever assembled. The hard hitting linebacker made his mark for the Monsters of the Midway and deserves to be celebrated while you’re out driving down Lake Shore Drive, hitting up the beach or going to Lollapalooza this summer.

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6. Derrick Rose Simeon jersey


I miss the old Derrick Rose, the dunking souls Rose, straight to the hole Rose, crossover cold D-Rose…

While we can all agree that Derrick Rose isn’t the same MVP player we all knew and loved, his Simeon days aren’t that far behind him when he was one of the hottest high school prospects in the nation. Rose is part of a list of Simeon alumni in the basketball world that is impressive. He also helped pave the way for future stars like Jabari Parker, who is a member of the Milwaukee Bucks.

For that reason alone, the Derrick Rose Simeon jersey is one to add to the collection.

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5. Walter Payton Bears jersey

1985: Running back Walter Payton #34 of the Chicago Bears looks on to pass during training camp in 1985. (Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images)

I’m not even a Bears fan and this one is high on my list to add to my personal collection. Everything that has been said about the man known as “Sweetness” has already been said: he is one of the greatest running backs in the history of the game, one of the greatest players to ever step on the field and one of the greatest men in NFL history.

To wear his jersey to wear it with honor and pride and truly represents the city of Chicago.

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4. Frank Thomas White Sox jersey


Frank Thomas, in my opinion, is one of the more underappreciated Chicago sports legends. He’s easily the best first basemen from either side of town and one of the better power hitters that the MLB has seen. Thomas has always conducted himself with grace and class, making his jersey a must own for any White Sox fan.

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3.  Michael Jordan rookie year Bulls jersey


This one gets the nod over just any Jordan jersey because of the cursive script that “Chicago” was written in and how beautiful the design is. In the years following the Bulls moved to the away jerseys they have now where “Bulls” is spelled out in more plain font. Also this is when Jordan had hair, so that’s fun.

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2. Ernie Banks Cubs jersey


Homage must be paid to the face of the Cubs franchise. Banks was not only an outstanding baseball player, but an amazing human being as well.

As far as Chicago Sports Mount Rushmore’s go, Ernie Banks deserves to be at the top. Any fan of Chicago baseball should be proud to have his jersey.

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1. Any Bulls Black and Red pinstripe jersey

NBA FILE: Dennis Rodman (91), Michael Jordan (23) and Scottie Pippen (33) of the Chicago Bulls.

If you can only afford to own one Chicago retro jersey, it has to be this. No ifs, and, or buts about it. Arguably the greatest design to ever be worn in Chicago for arguably the greatest team to ever play in the NBA, the 1996 Chicago Bulls. It doesn’t matter if you get a Dennis Rodman, Michael Jordan, Tony Kukoc, Scottie Pippen or even a Steve Kerr. This jersey and this look is a must own.

Is there anything I missed? Let us know in the comments or tweet at me @JChapmani65 on twitter

One thought on “Top 15 Chicago Retro jerseys to own for this summer

  • July 3, 2016 at 9:04 PM

    This list is incomplete without a 91-92 Blackhawks barber pole alternate jersey…which I own with LARMER 28 on the back.

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