Vintage 1990s Bears
This collection covers Chicago Bears sweatshirts made from 1990 to 1999. The decade followed the 1985 title team, and under Dave Wannstedt and Dick Jauron the Bears reached the playoffs only once, in 1994, with no return to the Super Bowl. Even so, a big fan base left plenty of fleece behind.
The identity was steady: navy and orange, the wishbone "C" introduced in 1962 and recolored orange with white and navy trim in 1974, and the "GSH" sleeve initials honoring George Halas since 1984. An orange bear-head logo arrived in 1999 as a secondary mark, which helps date late pieces. Logo 7, Starter, Salem Sportswear, Nutmeg Mills, Russell Athletic and Pro Player all made licensed Bears crewnecks. Period tags and crisp navy fleece set the best examples apart.
Bears · 90sWhich one to buy
34 Bears sweatshirts are listed but only a dozen with a fixed delivered price, so the $45–120 typical band is wide; most wearable crewnecks sit at $40–50. Prioritise a period tag (Champion, Russell Athletic, Logo 7, Starter, Nutmeg) and a stated size, and ask for pit-to-pit and length, since several here are Small, Medium or 4XL. Seller feedback wasn't captured for these listings, so check it on each item page. Red flags: a Champion XL at $240, over three times the median, and 'grunge' or 'distressed' titles priced like clean ones. Budget buyers should take the $38 navy graphic Medium, everyday wearers the $49 1996 Riddell Medium, and collectors the $60 Champion Reverse Weave.
- Listed now
- 34
- Damaged / for parts
- 0
- Typical ask
- $45–$120
- Full range
- $24–$240
Cheapest$38.26est. deliveredThe lowest delivered price here, about $38 on Buy It Now, for a navy graphic crewneck in Medium. No maker is named, so ask for a tag photo to confirm it's 90s, plus pit-to-pit, length and any stains.
Vintage 90s Chicago Bears Navy Graphic Sweatshirt (M)
View on eBay →$38.26 est. delivered
Best for beginners$49.49est. deliveredA 1996-dated crewneck with a Riddell tag in Medium at about $49 delivered, the low end of the band. Ask for pit-to-pit and length, since vintage Mediums fit small, and for photos of any cracking on the print.
Vintage Chicago Bears Sweatshirt Crewneck 1996 Men’s Medium Riddell
View on eBay →$49.49 est. delivered
Collector's pick$60.00deliveredChampion Reverse Weave is the sought-after 90s crewneck, and $60 with free shipping is a sane price next to a $240 Champion XL. It's tagged Small, though Reverse Weave runs wide and short, so ask for pit-to-pit, length and a tag photo.
Vintage 1990s Champion Chicago Bears Reverse Weave Crewneck Size Small
View on eBay →$60.00 delivered
Delivered prices include shipping as eBay quoted it to a US address on Oct 3, 2026. Many sellers charge by distance, so your total may differ; eBay shows your exact total before you buy.
Live on eBay right now
Snapshot captured — listings may have ended.
Delivered prices include shipping as eBay quoted it to a US address on Oct 3, 2026. Many sellers charge by distance, so your total may differ; eBay shows your exact total before you buy.
- Used
- Cheapest
Vintage 90s Chicago Bears Navy Graphic Sweatshirt (M)
$38.26est. delivered
$24.35 + $13.91 shipping
Buy It Now$24.35
Good buy
Navy graphic crewneck in Medium for about $38 delivered, the cheapest here; no maker named, so ask for a tag photo and pit-to-pit.
Seller: unknown
View on eBay →Used - Used
- Best for beginners
Vintage Chicago Bears Sweatshirt Crewneck 1996 Men’s Medium Riddell
$49.49est. delivered
$39.97 + $9.52 shipping
Buy It Now$39.97
Good buy
Dated 1996 with a Riddell tag, Medium, about $49 delivered; ask for pit-to-pit and photos of the graphic.
Seller: unknown
View on eBay →Used - Used
- Collector's pick
Vintage 1990s Champion Chicago Bears Reverse Weave Crewneck Size Small
$60.00delivered
$60.00 · free shipping
Buy It Now$60.00
Good buy
Champion Reverse Weave at $60 with free shipping, cheap for that tag, but it's a Small; Reverse Weave runs boxy, so check pit-to-pit.
Seller: unknown
View on eBay →Used 
UsedFruit Of The Loom Men's Vintage Chicago Bears Sweatshirt Heavy Tag USA
$49.99est. delivered
$40.00 + $9.99 shipping
Buy It Now$40.00
Offers accepted
This seller takes offers, and sellers often accept less than the asking price.
Fine if you might miss it? Send an offer first. Someone else can still buy it while you wait for a reply.
Want it for sure? Use Buy It Now.
Our take
Fruit of the Loom with a USA tag, consistent with 90s production, $50 delivered with Best Offer; the size isn't given, so ask for it.
Seller: unknown
View on eBay →Used
UsedUSA Made 90s NFL Big Size Sweatshirt 4XL Navy Brushed Lining CHICAGO B
$50.00est. delivered
$41.00 + $9.00 shipping
Buy It Now$41.00
Our take
A Made in USA 4XL with brushed lining for $50 delivered, a rare size in vintage that suits big-and-tall buyers; check pit-to-pit.
Seller: unknown
View on eBay →Used
UsedVintage 80s 90s Grunge Chicago Bears NFL Football Sweatshirt Distresse
$71.69est. delivered
$63.74 + $7.95 shipping
Buy It Now$63.74
Our take
Titled 'grunge' and 'distressed' and dated '80s 90s', about $72 delivered, which is band money for visible wear; see close-up photos first.
Seller: unknown
View on eBay →Used
UsedVINTAGE 90’S NFL CHICAGO BEARS RUSSEL ATHLETIC USA RARE SWEATSHIRT SIZ
$94.99est. delivered
$79.99 + $15.00 shipping
Buy It Now$79.99
Offers accepted
This seller takes offers, and sellers often accept less than the asking price.
Fine if you might miss it? Send an offer first. Someone else can still buy it while you wait for a reply.
Want it for sure? Use Buy It Now.
Our take
Russell Athletic Made in USA is period-correct, but about $95 delivered is high for an undescribed graphic; ask for size, tag and graphic photos.
Seller: unknown
View on eBay →Used
Used- Priced high
Vintage 90s CHAMPION Sweatshirt / NFL CHICAGO BEARS /Size:XL /Made in
$240.00delivered
$240.00 · free shipping
Buy It Now$240.00
Offers accepted
This seller takes offers, and sellers often accept less than the asking price.
Fine if you might miss it? Send an offer first. Someone else can still buy it while you wait for a reply.
Want it for sure? Use Buy It Now.
Heads-up: priced high
Champion Made in USA in XL, but $240 is over three times the median; nothing in the title explains the premium, so offer far lower.
Seller: unknown
View on eBay →Used
Prices and availability change daily. The full, current search on eBay shows every matching listing, including new ones since Oct 3, 2026.
See all current listings on eBay →typical asks, Oct 3, 2026
a fair price for a fair shirt
- The wishbone "C" in orange with white and navy trim has been unchanged since 1974, so the C alone won't date a piece.
- The orange bear-head logo became the team's secondary logo in 1999. A crewneck built around it is from the very end of the decade or later.
- Jersey-style graphics with "GSH" on the sleeve match the real uniforms from 1984 on.
- Maker tags of the decade: Logo 7 (renamed Logo Athletic in 1997), Starter, Salem Sportswear, Nutmeg Mills and its Lee Sport label (from 1995), Russell Athletic and Pro Player.
- Tag history narrows the date: Salem was sold to Fruit of the Loom in 1993 and folded into Pro Player, Russell ended its pro football licensing in 1997, and Logo Athletic and Starter were both bankrupt by about 1999.
- A copyright year printed under the graphic (for example, © 1994) plus licensing text such as "Officially Licensed NFL Product" or an NFL Properties mark. The year should agree with the tag and the construction.
- A Made in USA tag. Big makers moved sewing to Mexico and the Caribbean during the 90s, so a US-made tag supports an earlier date, while a Latin American tag usually points later in the decade.
- Licensed retro lines such as Mitchell & Ness (NFL throwbacks since about 2000, owned by Fanatics since 2022), Homage and Junk Food reprint old Bears logos on new blanks. Their own brand tags give them away, and Homage names designs by year (a '93 crewneck, for example), so a year in a listing title proves nothing.
- A Reebok tag dates NFL gear to 2002-2012, when Reebok held the league's exclusive uniform, sideline and cap license. A Nike tag is later still, since Nike took over the league's uniform contract in 2012.
- 1985 Super Bowl XX designs are among the most reprinted Bears graphics. On a 90s tag they can be period retro pieces; on a modern tag they are reissues.
- A familiar label is not automatic proof. Starter is still an active NFL licensee and the Nutmeg Mills name has been revived for vintage-style graphics, so check that the tag design, fabric and country of origin fit the period, not just the brand name.
- Dealers list the same red flags again and again: wrong neck tags for the era, missing licensing text, a copyright year that doesn't match the tag, and artificial distressing. A cut-out tag removes the best evidence, so price that piece as unverified.
Tagged sizes from the 90s don't line up neatly with modern sizing, and cotton-rich fleece shrinks in hot washes, which is why Champion patented its shrink-resisting Reverse Weave cut. Ask the seller for pit-to-pit and top-to-bottom length in inches and compare them with a sweatshirt you already own. A stretched waistband or blown-out cuffs will make it fit looser than the numbers suggest.
After Mike
Ditka is out after '92. Wannstedt wins one playoff game in '94, Erik Kramer has a career year in '95, and that's about it.
Looking for one specific design? The archive files every Bears design we found on eBay, one page each, with all its past examples.
How do I date a 90s Bears sweatshirt?
Use the maker tag first, then the copyright year under the print. The logo helps only at the edges: the orange bear head became a secondary logo in 1999, so pieces built around it are late or later.
Is the navy bear-head logo a 90s design?
A navy bear head was introduced as an alternate logo back in 1963, and the orange bear head followed in 1999. Either can appear on 90s merchandise, so rely on the tag and the print date.
Does single stitching matter on a vintage sweatshirt?
Not much. Single-stitch hems are a T-shirt dating tell, common on tees made before the late 1990s. Sweatshirts finish the cuffs and waist with ribbed bands, so judge a crewneck by its tag, its licensing text and the copyright year on the print instead.
Which maker should I look for?
Any intact 90s licensee tag: Logo 7 or Logo Athletic, Starter, Salem Sportswear, Nutmeg Mills or Lee Sport, Russell Athletic, or Pro Player. Demand follows the graphic more than the brand, but a missing tag makes any piece harder to date and value.