Prices increase in
-- H
-- M
-- S
Up to 40% Off Sitewide!
Shop Now

Windy Socks

Filter

Safe Search on hides explicit content. Safe Search off shows all results, including explicit content.
Paulie 14 Socks
Main Tag:  

Description: When you think of Chicago baseball on the Southside and the number 14, only one name should come to mind.

Tags: home run, all star, chicagoland, illinois, paulie

Paulie 14 Socks

by dSyndicate

$14 $20

for
--
:
--
:
--

Chicago Baseball Crossed Bats 1876 Socks
Main Tag:  

Description: Classic Chicago baseball aesthetic with crossed bats. Honors the long history of the game in the Windy City.

Tags: 1876, baseball, chicago, crossed bats, cubs

Chicago Baseball Crossed Bats 1876 Socks

by OuterKitsch

$14 $20

for
--
:
--
:
--

y Chicago Flag Grey Small Socks

Description: **Styley Chicago Flag Grey Small** City pride subtly displayed. Grey tones meet iconic stripes and stars in a compact, stylish rendition of a beloved civic symbol.

Tags: chica, chicago local spirit, custom city themed, unique city vibe, urban city pride

y Chicago Flag Grey Small Socks

by Nutty Jam

$14 $20

for
--
:
--
:
--

Retro Chicago Sting Soccer Socks
Main Tag:  

Description: The Chicago Sting (1974–1988) was an American professional soccer team representing Chicago. The Sting played in the North American Soccer League from 1975 to 1984 and in the Major Indoor Soccer League in the 1982–83 season and again from 1984 to 1988. They were North American Soccer League champions in 1981 and 1984, one of only two NASL teams (the New York Cosmos) to win the championship twice.

Tags: bulls, chi town, chicago cubs, chicity, fifa

Retro Chicago Sting Soccer Socks

by Localzonly

$14 $20

for
--
:
--
:
--

DeMar DeRozan Street Socks
Main Tag:  

Description: DeMar DeRozan Street Vintage Style

Tags: basketball, bulls, chi town, chicago bulls, deebo

DeMar DeRozan Street Socks

by All Time Ballers

$14 $20

for
--
:
--
:
--

Chicago City Gradient Socks
Main Tag:  

Description: Vibrant Chicago city gradient design with purple, pink colors. Perfect for Chicago lovers and city enthusiasts.

Tags: chicago band, chicago city, city, gradient, illinois

Chicago City Gradient Socks

by stillo.official

$14 $20

for
--
:
--
:
--

Chicago Love Flag Socks

Description: Show your love of Chicago with this Chicago flag

Tags: vintage, windy city, illinois, chicago love, chicago

Chicago Love Flag Socks

by Buffalo Drygoods

$14 $20

for
--
:
--
:
--

CHICAGO Smoking Gun 90s Style Graphic Socks
Main Tag:  

Description: CHICAGO Smoking Gun 90s Style Graphic

Tags: city life, chicago illinois, chicago lover, smoking gun detroit, smoking gun

CHICAGO Smoking Gun 90s Style Graphic Socks

by DarkLordPug

$14 $20

for
--
:
--
:
--

Chicago Wrigleyville Star Logo Vintage Emblem Distressed Version Socks
Main Tag:  

Description: A vintage looking logo for the City of Chiacago's Wrigleyville

Tags: ballpark, baseball, chicago, cubbies, cubs
Napoleon Dynamite Nick Foles Chicago Bears Socks
Main Tag:  

Description: Napoleon Dynamite Nick Foles Chicago Bears

Tags: bear down, bears, chi town, chicago, chicago bears

Napoleon Dynamite Nick Foles Chicago Bears Socks

by stayfrostybro

$14 $20

for
--
:
--
:
--

Chicago's Very Own Socks
Main Tag:  

Description: WGN Channel 9 Chicago // Vintage 80s Style Fan Design

Tags: 9, chicago, chitown, illinois, local

Chicago's Very Own Socks

by FriendGate

$14 $20

for
--
:
--
:
--

Windy City Series  - Kai Rhodes 21, Caught Up, Liz Tomforde, book lover Socks
Main Tag:  

Description: A book-inspired design celebrating the world of sports romance through iconic characters like Kai Rhodes and the Windy City series. With a sleek, modern aesthetic, it reflects the intensity of athletics blended with emotional storytelling and character-driven romance. Perfect for readers who love competitive energy, strong personalities, and heartfelt moments, this artwork captures the spirit of contemporary romance within a sports-driven setting.

Tags: book lover, caught up, evan zanders, isaiah rhodes, kai rhodes
Good Better Best Chicago Football Socks
Main Tag:  

Description: Good Better Best Chicago Football

Tags: 2025 champions, bear down, caleb williams, chicago bears, chicago football

Good Better Best Chicago Football Socks

by kobishadesignVip

$14 $20

for
--
:
--
:
--

I Love Chicago | Chicago Pride | Windy City Love and Adventure Design Socks
Main Tag:  

Description: Show your love for the Windy City with this bold and stylish design! Perfect for Chicago residents, visitors, and anyone who adores the vibrant culture, iconic skyline, and unforgettable energy of Chicago. Celebrate the heart of Illinois in true Windy City style!

Tags: chicago, chicago culture, chicago flag, chicago illinois, chicago lovers
CHICAGO Socks
Main Tag:  

Description: Best For you, Get ready now

Tags: united states, united states of america, chicago bulls, air jordan, michael jordan

CHICAGO Socks

by Aspita

$14 $20

for
--
:
--
:
--

Chicago, Windy City Socks
Main Tag:  

Description: Chicago, Windy City

Tags: tshirtdesign

Chicago, Windy City Socks

by Tees and the Cities

$14 $20

for
--
:
--
:
--

Chicago Express Basketball Socks
Main Tag:  

Description: Defunct Chicago Express Basketball 1988-1992

Tags: basketball, chicago il, chicago illinois, defunct, defunct logo

Chicago Express Basketball Socks

by KTees Emporium

$14 $20

for
--
:
--
:
--

Metal Detector - I dig Heavy Metal Socks

Description: This is for those hardcore metal detectorist out there that love digging metal. Finding those old relics on farms and historical wars sites is where it's at. Designed my the Windy Digger Merchandising Company

Tags: windy digger, metal detectorist humor, metal detectorist slogan, metal detecting gifts lover, metal detect

Metal Detector - I dig Heavy Metal Socks

by Windy Digger Apparel

$14 $20

for
--
:
--
:
--

Chicago Hockey Classic Helmet Socks
Main Tag:  

Description: Vintage Chicago hockey design with a retro goaltender/player helmet. Established 1926 heritage style.

Tags: 1926, chicago, helmet, hockey, ice hockey

Chicago Hockey Classic Helmet Socks

by OuterKitsch

$14 $20

for
--
:
--
:
--

Chicago Baseball Dark Retro Socks
Main Tag:  

Description: Distressed Chicago baseball diamond graphic with a classic vintage 90s sports vibe.

Tags: 90s, baseball, chi town, chicago, illinois

Chicago Baseball Dark Retro Socks

by OuterKitsch

$14 $20

for
--
:
--
:
--

Indy's playbook, Vintage Right move, Windy City Series, Liz Tomforde, Play Along, Caught Up, Mile High, Rhodes, Book lover Socks

Description: A vintage-inspired design capturing the spirit of Indy’s Playbook within the Windy City series. Blending retro aesthetics with modern sports romance storytelling, it reflects the layered relationships and dynamic characters that define the series. With subtle references to fan-favorite names and moments, this artwork speaks to readers who love heartfelt romance, competitive energy, and immersive bookish worlds.

Tags: book, book lover, caught up, isaiah rhodes, kai rhodes
Magnificent Mile Chicago Arch Text Socks
Main Tag:  

Description: Show your love for the Windy City with this classic athletic-style arched text . Featuring bold lettering, this piece captures the spirit of downtown walking, shopping, and urban exploration in Chicago. Perfect for locals and visitors who appreciate iconic city landmarks and a clean, sporty aesthetic.

Tags: downtown, illinois, travel, urban, windy city

Magnificent Mile Chicago Arch Text Socks

by Endless Siege

$14 $20

for
--
:
--
:
--

Chicago Riverwalk Vintage Athletic Style Socks
Main Tag:  

Description: Celebrate the iconic urban scenery of the Windy City with this classic vintage-inspired graphic. Featuring bold, athletic-style lettering, this piece is perfect for locals, tourists, and anyone who loves strolling along the water. Show your appreciation for this famous landmark with a timeless and clean aesthetic.

Tags: illinois, landmark, riverwalk, urban, windy city

Chicago Riverwalk Vintage Athletic Style Socks

by Maskind

$14 $20

for
--
:
--
:
--

Chicago Retro Style Vintage Sport Typography Socks
Main Tag:  

Description: Show your love for the Windy City with this bold, vintage-inspired typography featuring a classic athletic arched font and sleek horizontal stripes. Perfect for locals, travelers, or anyone who appreciates clean, retro aesthetic urban style. Ideal for wearing while exploring the neighborhood streets or relaxing with friends.

Tags: athletic, illinois, retro, urban, windy city

Chicago Retro Style Vintage Sport Typography Socks

by zaflab

$14 $20

for
--
:
--
:
--

Chicago Skyline Blue Retro 1833 Socks
Main Tag:  

Description: Celebrate the Windy City with this vintage-inspired graphic. Features a bold Chicago skyline silhouette and classic typography, perfect for showing your Midwestern spirit and city pride.

Tags: 1833, retro, skyline, urban, windy city

Chicago Skyline Blue Retro 1833 Socks

by Yakis gagap crafted

$14 $20

for
--
:
--
:
--

Chicago Star Typography Minimalist Streetwear Socks
Main Tag:  

Description: Showcase your love for the windy city with this sleek, minimalist typography featuring the iconic multi-pointed municipal star. Perfect for urban explorers, architecture fans, and proud locals looking for modern streetwear apparel and stylish urban accessories.

Tags: minimalist, star, typography, urban, windy city
Chicago Vintage Retro Style Sport Text Socks
Main Tag:  

Description: Show your love for the Windy City with this retro-inspired graphic featuring bold block lettering and classic triple stripes. Perfect for locals and visitors alike, this clean and minimalist aesthetic captures a timeless urban vibe that pairs perfectly with any casual outfit or street style look.

Tags: illinois, retro, urban, vintage, windy city

Chicago Vintage Retro Style Sport Text Socks

by MicroShop

$14 $20

for
--
:
--
:
--

Chicago City of Big Shoulders Skyline Blue Socks
Main Tag:  

Description: Celebrate the Windy City with this stylish Chicago skyline graphic. Featuring the iconic Ferris wheel and urban architecture in a vibrant blue aesthetic, this piece captures the spirit of the Midwest. Perfect for locals, travelers, or anyone who loves urban landscapes and historic city landmarks.

Tags: architecture, illinois, midwest, skyline, windy city

Chicago City of Big Shoulders Skyline Blue Socks

by Ur Secret Lover

$14 $20

for
--
:
--
:
--

Chicago Illinois Vintage Arch Sport Typography Socks
Main Tag:  

Description: Bold athletic arched text representing the city of Chicago in Illinois.

Tags: athletic, hometown, illinois, varsity, windy city

Chicago Illinois Vintage Arch Sport Typography Socks

by REOSINS

$14 $20

for
--
:
--
:
--

Hands-Off-Chicago Socks

Description: Hands-Off-Chicago

Tags: chicago, chicago defender, chicago heritage, chicago locals, chicago lovers

Hands-Off-Chicago Socks

by FestiveThreadsCo

$14 $20

for
--
:
--
:
--

Classic Chicago Marathon 1979 Socks
Main Tag:  

Description: The Chicago Marathon is a marathon held every October in Chicago, Illinois. It is one of the six World Marathon Majors. Thus, it is also a World Athletics Label Road Race. The Chicago Marathon is the fourth-largest race by number of finishers worldwide. The men's and women's races were won by Americans Dan Cloeter (2:23:20 hours) and Laura Michalek (3:15:45).

Tags: 70s, 80s, chicago illinois, exercise, fitness

Classic Chicago Marathon 1979 Socks

by Localzonly

$14 $20

for
--
:
--
:
--

Al Capone 'Snorky' Portrait Logo - Chicago Outfit Socks
Main Tag:  

Description: Embrace the iconic legacy of Al Capone, known as 'Snorky,' with my unique Logo Design. Paying tribute to the infamous Chicago Outfit, this apparel design captures the essence of the Prohibition-era gangster. Wear the legend, wear the style on my t-shirts and apparel.

Tags: al capone, chicago history, chicago mob, chicago outfit, crime boss
Santo 10 Socks
Main Tag:  

Description: When you think of Chicago baseball on the Northside and the number 10, only one name should come to mind.

Tags: sports, windy city, hof, chicago, baseball gifts

Santo 10 Socks

by dSyndicate

$14 $20

for
--
:
--
:
--

Chicago Dog with Flag Socks
Main Tag:  

Description: Just a weiner dog with toppings and the flag of Chicago!

Tags: chicago, vector, hotdog, food, chicity

Chicago Dog with Flag Socks

by DangerHuskie

$14 $20

for
--
:
--
:
--

Chicago Shamrox Lacrosse Socks
Main Tag:  

Description: Defunct Chicago Shamrox Lacrosse 2907-2008

Tags: chi town, chicago, chicago il, chicago illinois, chicity

Chicago Shamrox Lacrosse Socks

by KTees Emporium

$14 $20

for
--
:
--
:
--

Land of the Black Sun Socks
Main Tag:  

Description: Chicago skyline at sunset, with flag stars design

Tags: skyline, chicago flag, chi town, pride, lgbt

Land of the Black Sun Socks

by Jeremy Lampkin

$14 $20

for
--
:
--
:
--

Similar Designs

Cart Preview (0)

Adult Apparel

Kids Apparel

Accessories

Home Goods