Celebrate the YOLO spirit with our Chicago inspired Team YOLO Flag apparel collection, featuring boldly styled hats, sportswear, activewear, hoodies, and outerwear featuring our black, blue, and red star brand logo flag.
Perfect for Chicagoans and Team YOLO fans alike, these designs combine bold style with local pride. Whether you're looking for a trendy new rope hat or trucker hat or making a bold fashion statement, YOLO Golf Sportswear and Activewear has everything to rep your love for the Windy City. Explore now and save when you bundle!
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42 products
42 products



YOLO-Chicago Flag Patch Rope Cap
YOLO-Chicago Flag Patch Rope Cap
The Ultimate Chicago Flex 💪 YOLO-Chicago Flag Patch Rope Cap
WHY YOU’LL LOVE IT
✔️ High-quality embroidered Chicago-YOLO flag patch for a standout look.
✔️ Relaxed fit and lightweight design for all-day comfort.
✔️ Adjustable, contrast colored snapback closure for the perfect fit.
✔️ Semi-curved bill with contrast decorative rope for a classic yet sporty vibe.
PRODUCT SPECS
✔️ Material: 70% Cotton / 30% Nylon.
✔️ 5-panel construction for premium comfort.
✔️ Half-moon mesh interior for breathability.
Show off your love for Chicago with this fresh, modern cap.
A high-quality embroidered flag patch and striking rope and snapback detail make this hat the perfect blend of style and city spirit.
🎯 Don’t wait—stock is limited! Snag your YOLO-Chicago Flag Patch Rope Cap today and wear your city pride wherever you go!



Ocean Mist Swingman Eco-Tee Polo Shirt | YOLO Golf Sportswear
$49.95 USD
Unit price / perOcean Mist Swingman Eco-Tee Polo Shirt | YOLO Golf Sportswear
$49.95 USD
Unit price / perDiscover the Ocean Mist Swingman Eco-Friendly Men's Slim-Fit Polo Shirt from Team YOLO Golf Activewear-Sportswear —where performance meets sustainability.
Crafted with 84% recycled polyester and 16% spandex, this environment conscious modern fit polo embodies style, comfort, and respect for the planet.
Designed for golfers who value quality on and off the course, it features a fitted but comfortable look and premium functionality.
Timeless Modern Tailoring
✔️ Finished with two premium-quality natural shell buttons for a polished look
✔️ Modern slim-fit with a sleek, versatile style that transitions effortlessly from course to clubhouse. Size up if you prefer a looser more relaxed fit polo shirt.
✔️ Features the fashionable YOLO Golf Swingman Logo on the front chest and YOLO Flag on the upper back
High-Performance Fabric
✔️ Moisture-wicking to keep you cool through every swing
✔️ Quick-drying for all-day comfort
✔️ 84% recycled poly/16% spandex with four-way stretch for unrestricted movement
✔️ Breathable to maintain comfort in all conditions
✔️ UPF 50+ sun protection to keep you safe on sunny days
Eco-Friendly Commitment
✔️ Made with recycled polyester sourced from 8-9 plastic bottles per polo
✔️ Sustainable production that reduces environmental impact
✔️ Crafted by certified manufacturers dedicated to ethics, compliance, and social responsibility
Machine wash gentle cycle at 30 degrees Celsius; Do not bleach; Tumble dry low; Do not iron; Do not dry clean.
Each Team YOLO Golf Polo is crafted to meet the high standards of both performance and ethics, allowing you to play your best while making a positive impact. Get your Ocean Mist Eco-Tee Slim-Fit polo shirt today!
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Team YOLO Mid-Profile Contrast Rope Trucker Hat
$29.95 USD
Unit price / perTeam YOLO Mid-Profile Contrast Rope Trucker Hat
$29.95 USD
Unit price / per

No-Limit Quick-Dry Stretch Polo Shirt | YOLO Golf
From $54.95 USD
Unit price / perNo-Limit Quick-Dry Stretch Polo Shirt | YOLO Golf
From $54.95 USD
Unit price / per

Quick-Dry Lightweight Performance Polo | YOLO Golf-adidas
From $54.95 USD
Unit price / perQuick-Dry Lightweight Performance Polo | YOLO Golf-adidas
From $54.95 USD
Unit price / per

Carbon Drift Performance Joggers - Gray Heather
From $39.95 USD
Unit price / perCarbon Drift Performance Joggers - Gray Heather
From $39.95 USD
Unit price / per

Pigment-Dyed Performance Tri-Blend Zip Hoodie | Team YOLO
Pigment-Dyed Performance Tri-Blend Zip Hoodie | Team YOLO


Carbon Drift Performance Joggers - Charcoal Heather
From $39.95 USD
Unit price / perCarbon Drift Performance Joggers - Charcoal Heather
From $39.95 USD
Unit price / per

Dark Matter Wide-Leg Baggy Joggers | Stretch Jersey Track Pants
From $39.95 USD
Unit price / perDark Matter Wide-Leg Baggy Joggers | Stretch Jersey Track Pants
From $39.95 USD
Unit price / per

The Edgewalker 2 Canvas Sneakers | Black Team YOLO Edition
$59.95 USD
Unit price / perThe Edgewalker 2 Canvas Sneakers | Black Team YOLO Edition
$59.95 USD
Unit price / per

Hooded Windbreaker Rain Jacket | Team YOLO Black Edition
From $64.95 USD
Unit price / perHooded Windbreaker Rain Jacket | Team YOLO Black Edition
From $64.95 USD
Unit price / per

Soft Unisex Athletic Heather T-Shirt | YOLO Sport
Soft Unisex Athletic Heather T-Shirt | YOLO Sport


Competitor 4-way Stretch Q-Zip Pullover | YOLO Golf
From $39.95 USD
Unit price / perCompetitor 4-way Stretch Q-Zip Pullover | YOLO Golf
From $39.95 USD
Unit price / per

Super-Soft Tri-Blend Unisex Athletic T-Shirt | Team YOLO Flag
From $29.95 USD
Unit price / perSuper-Soft Tri-Blend Unisex Athletic T-Shirt | Team YOLO Flag
From $29.95 USD
Unit price / per

Eco-Fit Quick-Dry Q-Zip Pullover | UPF 50+ Team YOLO Edition
$49.95 USD
Unit price / perEco-Fit Quick-Dry Q-Zip Pullover | UPF 50+ Team YOLO Edition
$49.95 USD
Unit price / per

The Edgewalker 1 Canvas Sneakers
The Edgewalker 1 Canvas Sneakers


Fabric-Lined Flip-Flop Sandals | Team YOLO Flag
$15.95 USD
Unit price / perFabric-Lined Flip-Flop Sandals | Team YOLO Flag
$15.95 USD
Unit price / per

Competitor Cool-Fit Quick-Dry Athletic T-Shirt
Competitor Cool-Fit Quick-Dry Athletic T-Shirt
What People Are Saying
⭐⭐⭐⭐⭐
My YOLO Golf circle logo cap is already my favorite and my neighbor gave me a compliment. Premium quality, looks great!
- Chris R.
⭐⭐⭐⭐⭐
Great material and fit. Not too slim and not too loose. The fabric weight is perfect too. Not too thin but not too thick either. Very soft, love the logo!
- Eddie E.
⭐⭐⭐⭐⭐
Fall golf is here and this is just what I needed. Impressed by the quality for the price and love this YOLO logo patch.
- Francis B.
⭐⭐⭐⭐⭐
Add customer reviews and testimonials to showcase your store's happy customers
- Chelsea H.
⭐⭐⭐⭐⭐
Had to have this hat! The stitching is nicely done. I prefer lighter breathable cotton-blend caps especially on hot sunny days and this is what I needed.
- Reese M.
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