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Brooks has 32" waist wearing size 32
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
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Men's Tradewind Short

Regular Price $88
If you're in between sizes, we recommend sizing down
4.8
Rated 4.8 out of 5 stars
173
Regular Price $88
Size
Hurry! Only 63 left in stock!

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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.

UPF 50+ Sun
Protection

Quick Dry

Moisture Wicking

Materials & Care

Material Description: Ultra-soft, stretch woven with DWR
Material Contents: 73% Repreve Polyester / 19% Organic Cotton / 8% Spandex + DWR
Fabric Weight (GSM): 150

Size & Fit

True to size with added stretch that moves with you
Classic chino fit
Straight leg
7.5” Inseam / 18.5” Outseam

Shipping & Returns

Free standard shipping on all orders $150+
Free 30-day returns and 60-day exchanges on U.S. orders for unwashed, unworn items.
Final sale styles are not eligible for return or exchange.
Send gifts wrapped by adding on gift wrap at cart. We also offer free gift messaging.

Tradewind Short
30
4.8
Rated 4.8 out of 5 stars
Based on 173 reviews
Total 5 star reviews: 154 Total 4 star reviews: 7 Total 3 star reviews: 6 Total 2 star reviews: 4 Total 1 star reviews: 2
FitRated 0.2 on a scale of minus 2 to 2
173 reviews
  • sharyn b.
    Verified Buyer
    Rated 5 out of 5 stars
    30 minutes ago
    Reviewing
    Men's Tradewind Short - Cement Cement / 34
    Anniversary gift

    My husband loved the shirt and shorts. Materials were perfect.

    What is your height? 5'10-6'0
    What is your weight? 160-180
    What size did you purchase? 34
    For what activity do you recommend this product? Casual Wear
  • Bonnie A.
    Verified Buyer
    Rated 5 out of 5 stars
    8 hours ago
    Reviewing
    Men's Tradewind Short - Slate Blue Slate Blue / 34
    He loves them!

    He loves the fit!

    What is your height? 5'10-6'0
    What is your weight? 160-180
    What size did you purchase? 34
    For what activity do you recommend this product? Casual Wear
  • James J.
    Verified Buyer
    Rated 5 out of 5 stars
    4 days ago
    Reviewing
    Men's Tradewind Short - Slate Blue Slate Blue / 38
    4th pair

    Love these shorts, but the sizes run big. Order the next size down.

    What is your height? 6'1-6'3
    What is your weight? 200-220
    What size did you purchase? 38
    For what activity do you recommend this product? Casual Wear, Fishing, Hiking, Work, Travel
    FF Profile picture for Free Fly Apparel
    Free Fly Apparel
    3 days ago

    Hey there! Thanks so much for this feedback. I'm so happy to hear you are loving the Tradewind Short! Thanks so much for the insight on the sizing, I will be sure to pass this along. We appreciate you!

  • TYLER B.
    Verified Buyer
    Rated 5 out of 5 stars
    5 days ago
    Reviewing
    Men's Tradewind Short - Smoke Smoke / 38
    The Best Shorts hands down

    So I have a lot of free fly shirts and I recently started buying the reverb and breeze shorts for men and I couldn’t stop talking about them. We go on vacation to Florida and I told my wife I was tired of lugging around my heavy American eagle shorts so I went to a store and found some trade winds shorts let me just say that sold me from there so of course as soon as I got home I ordered this pair to go with my others and I will most definitely be ordering more you can’t beat the softness and how light they are unbelievable!

    What is your height? 5'10-6'0
    What is your weight? 220-240
    What size did you purchase? 38
    For what activity do you recommend this product? Casual Wear, Travel, Work
  • Reggie F.
    Verified Buyer
    Rated 5 out of 5 stars
    6 days ago
    Reviewing
    Men's Tradewind Short - Smoke Smoke / 38
    Pleasantly surprised!

    These are some of the most comfortable shorts that I have owned.

    What is your height? 6'1-6'3
    What is your weight? 220-240
    What size did you purchase? 38
    For what activity do you recommend this product? Casual Wear, Fishing, Hiking
  • John M.
    Verified Buyer
    Rated 5 out of 5 stars
    1 week ago
    Reviewing
    Men's Tradewind Short - Cement Cement / 36
    Great shorts for everything.

    Perfect all around shorts. Fishing, golf, travel or out to a summer dinner. Nice cut, as not too full or too tight.

    What is your height? 6'1-6'3
    What is your weight? 180-200
    What size did you purchase? 36
    For what activity do you recommend this product? Casual Wear, Fishing, Travel
  • Terrie M.
    Verified Buyer
    Rated 5 out of 5 stars
    2 weeks ago
    Reviewing
    Men's Tradewind Short - Slate Blue Slate Blue / 32
    Mens Tradewind Shorts

    Great fit, light weight material

    What is your height? 5'7-5'9
    What is your weight? 140-160
    What size did you purchase? 32
    For what activity do you recommend this product? Casual Wear
  • Anthony W.
    Verified Buyer
    Rated 5 out of 5 stars
    3 weeks ago
    Reviewing
    Men's Tradewind Short - Cement Cement / 32
    Great Shorts

    Great fit and quality. Super lightweight and comfortable. I just the Tradewind Pant came in a longer length than 32".

    What is your height? 6'1-6'3
    What is your weight? 180-200
    What size did you purchase? 32
    For what activity do you recommend this product? Casual Wear

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Tradewind Short

4.8
Rated 4.8 out of 5 stars
173
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
Men's Tradewind Short - Chestnut Men's Tradewind Short - Chestnut
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