One Size Doesn't Fit All
All measurements are in inches and reflect body measurements. If you are in between sizes, size up for comfort. Got questions? Email us at info@freeflyapparel.com.
Men
Women
Toddler
Youth
| Alpha Sizes | Numeric Sizes | Chest | Waist | Hip | Sleeve |
|---|---|---|---|---|---|
| S | 30–31 | 36–38 | 30–32 | 34–37 | 32–33 |
| M | 32–33 | 38–40 | 32–34 | 37–39 | 33–34 |
| L | 34–35 | 41–43 | 35–37 | 40–42 | 34–35 |
| XL | 36–38 | 44–46 | 38–40 | 43–45 | 35–36 |
| XXL | 40 | 47–49 | 41–43 | 46–48 | 36–37 |
| 3XL | 50–52 | 44–46 | 49–51 | 36–37 |
How to Measure Yourself
-
CHEST
Measure circumference from the widest part around chest, about 1” down from armpit.
-
SLEEVE
With arm slightly bent, measure from center back neck to shoulder, down arm to wrist bone.
-
TRUE WAIST
Measure around your natural waist, narrowest part of your torso.
-
HIP
Measure around the fullest part of your hips.
Free Returns & Exchanges
If you try it and it doesn't fit, no problem. Returns and exchanges are free and easy. Learn More
Men's Tradewind Short
Why You'll Love It
Feels like sweats, looks like you tried. The Tradewind Short combines the best of both worlds—a timeless chino fit and a super soft, organic cotton blend finished with DWR for unbeatable comfort in hot, humid, and near-the-water destinations. Perfect for travel, golf, or casual everyday wear, it’s packed with freedom-granting stretch that won’t hold you back. Pair it with our Elevate Polo when you’re meeting buddies on the course, or try it with the Motion Tee for a go-to weekend look.
One Size Doesn't Fit All
All measurements are in inches and reflect body measurements. If you are in between sizes, size up for comfort. Got questions? Email us at info@freeflyapparel.com.
Men
Women
Toddler
Youth
| Alpha Sizes | Numeric Sizes | Chest | Waist | Hip | Sleeve |
|---|---|---|---|---|---|
| S | 30–31 | 36–38 | 30–32 | 34–37 | 32–33 |
| M | 32–33 | 38–40 | 32–34 | 37–39 | 33–34 |
| L | 34–35 | 41–43 | 35–37 | 40–42 | 34–35 |
| XL | 36–38 | 44–46 | 38–40 | 43–45 | 35–36 |
| XXL | 40 | 47–49 | 41–43 | 46–48 | 36–37 |
| 3XL | 50–52 | 44–46 | 49–51 | 36–37 |
How to Measure Yourself
-
CHEST
Measure circumference from the widest part around chest, about 1” down from armpit.
-
SLEEVE
With arm slightly bent, measure from center back neck to shoulder, down arm to wrist bone.
-
TRUE WAIST
Measure around your natural waist, narrowest part of your torso.
-
HIP
Measure around the fullest part of your hips.
Free Returns & Exchanges
If you try it and it doesn't fit, no problem. Returns and exchanges are free and easy. Learn More
UPF 50+ Sun
Protection
Quick-Dry
Moisture-Wicking
- BryanRated 5 out of 5 stars2 days agoReviewingMen's Tradewind Short - Smoke Smoke / 365 Stars
Soft. Comfortable. You can do anything in these. Definitely a go to short.
- Kathleen M. S.Verified BuyerRated 3 out of 5 stars5 days agoReviewingMen's Tradewind Short - Cement Cement / 34Nice but color is off
The color is much much darker than picture. The fabric is great for causal or dress
What is your height? 6'1-6'3What is your weight? 180-200What size did you purchase? 34 - Kathleen M. S.Verified BuyerRated 5 out of 5 stars5 days agoReviewingMen's Tradewind Short - Vintage Khaki Vintage Khaki / 34Classic and comfortable.
The fabric is breathable yet can be dressed or down
What is your height? 6'1-6'3What is your weight? 180-200What size did you purchase? 34 - Clayton H.Verified BuyerRated 5 out of 5 stars1 week agoReviewingMen's Tradewind Short - Smoke Smoke / 34Great product
Fit as described. I will be buying more!
What is your height? 5'7-5'9What is your weight? 160-180What size did you purchase? 34For what activity do you recommend this product? Casual Wear - Anthony H.Verified BuyerRated 5 out of 5 stars2 weeks agoReviewingMen's Tradewind Short - Slate Blue Slate Blue / 36Fantastic Shorts
Best Fit shorts I own!
What is your height? 5'7-5'9What is your weight? 200-220What size did you purchase? 36For what activity do you recommend this product? Casual Wear - Andrew R.Verified BuyerRated 5 out of 5 stars2 weeks agoReviewingMen's Tradewind Short - Slate Blue Slate Blue / 34Great fit
Comfortable and soft
What is your height? 5'10-6'0What is your weight? 180-200What size did you purchase? 34For what activity do you recommend this product? Fishing, Casual Wear - Chris P.Verified BuyerRated 5 out of 5 stars2 weeks agoReviewingMen's Tradewind Short - Vintage Khaki Vintage Khaki / 34Great shorts
love these shorts, very comfortable, lightweight, and just the right casual look and length. Great value for the end of the year clearance sale especially hard to resist, thanks!
What is your height? 6'1-6'3What is your weight? 160-180What size did you purchase? 34x32For what activity do you recommend this product? Casual Wear, Travel, Work - Bryan J.Verified BuyerRated 5 out of 5 stars2 weeks agoReviewingMen's Tradewind Short - Vintage Khaki Vintage Khaki / 36Fantastic shorts
Lightweight, just the right fit, and they strike the perfect balance between weekend golf and date night.
What is your height? 6'1-6'3What is your weight? 220-240What size did you purchase? 36For what activity do you recommend this product? Casual Wear, Work, Travel