Cultural Context
'On my shit' is street for locked in — fully focused, handling business. Chicago is a grind-it-out town where the hustle is the culture and winters forge thick skin. Wearing I'M ON MY CHICAGO SHIT TODAY says the day can bring whatever — Chi-Town's seen worse.

I'm On My Chicago Shit Today (Bullet Holes) — Sweatshirt

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Sweatshirt  ·  Street Talk Designs
$39.99
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Color: Ash
Size: S

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About This Piece

I'M ON MY CHICAGO SHIT TODAY is Windy City steel — “on my shit” means locked in with a thick skin.

Chicago doesn't do soft: lake-effect winters, a grind-it-out town where the hustle is the culture. The bullet holes mark the kind of focus that took hits and kept moving.

This is for the Midwest grinders who treat every day like a work shift — the ones Chicago raised to be unshakeable.

The statement is armor and announcement in one. Wearing it says the day can bring whatever — Chi-Town's already seen worse.

Windproof. Weatherproof. Worry-proof.

Explore the language of cities and states.

Shop Ya City and State Unfiltered — the raw cuts, no filter.

Garment details & care

Sweatshirt — Gildan 18000

Product features:

  • Medium-heavy 50/50 cotton-poly blend (8.0 oz/yd²) for durability and warmth
  • Tubular knit with no side seams and ribbed collar for cleaner fit and shape retention
  • Embroidery placement options: left chest, center chest, large center chest, and wrists
  • DTF printed inner neck labels and wrist prints; primary prints via DTG
  • Ethically sourced US cotton and OEKO-TEX® STANDARD 100 certified dyes; double-needle stitched seams

Care instructions:

  • Machine wash: cold (max 30C or 90F)
  • Non-chlorine: bleach as needed
  • Tumble dry: low heat
  • Do not dryclean
  • Do not iron.
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Questions Answered
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Frequently Asked Questions

What does “I'm On My Chicago Shit Today” mean?

“On my shit” means locked in — focused and handling business — and the Chicago version brings steel: thick-skinned, grind-tested, unshakeable. Windy City focus with a work-shift mentality.

Is this about being in a bad mood?

No — it's the Midwest grind in shirt form. 'On my shit' is the locked-in mode; Chicago just makes it weatherproof. Armor, not attitude.

What makes this a good gift?

It's the gift for the Chicago lifer — the one who treats every day like a work shift and outworks the weather. Steel-town pride, never generic.

Where can I wear this?

Work grinds, gym sessions, lakefront runs — anywhere the day needs handling. It's built for Chicago's toughest rooms.

How should I style this?

Chicago uniform: jeans, boots, layers that laugh at the lake effect. The shirt's already steel — dress to match.

Every Statement Has a Cultural Source

Street Talk Designs is rooted in documented hip-hop and urban street language. OG Randy, born and raised in Brooklyn, spent years documenting the language of the culture in Street Talk: Da Official Guide To Hip-Hop and Urban Slanguage. Some designs use documented slang; others draw from the broader cultural territory of humor, family, faith, personality, and everyday expression.

Explore The Slang Academy →
10K+
Documented Entries
700
Pages of Vernacular
15
Years Documented
5K+
Statement Designs
I'm On My Chicago Shit Today (Bullet Holes) — Sweatshirt$39.99

Size Guide

SizeChest (in)Length (in)Sleeve (in)
S202733
M222834
L242935
XL263036
2XL283137
3XL303238
4XL323339
5XL343440

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