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Sale price $99Guaranteed delivery by Christmas.
Other items in this collection
Peach Triangle Geo
Product Options
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Choose your Fit
Choose your Length
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Product Information
The Leeward is a lightweight, wrinkle-resistant performance dress shirt with built-in stretch. Designed for easy care, breathable comfort, and all-day wear—no dry cleaning needed.
Performance Features
– 4-Way Stretch
– Moisture-Wicking
– Breathable
– Wrinkle-Resistant
– Lightweight
Construction
– Short Sleeves
– Hidden Button-Down Collar
– Back Darts
– Our short sleeves are designed to be worn untucked and are 2 inches shorter in length than our regular dress shirt
Body Length
– Small: 28 3/8"
– Medium: 29"
– Large: 29 5/8"
– X-Large: 30 1/4"
– XX-Large: 30 7/8"
SKU: 1WS-1576
Model is 6’ 2” and is wearing a Medium, Trim Fit, Regular Length
– Lightweight feel, ideal for year-round wear
– Moisture-wicking, breathable, wrinkle-resistant, 4-way stretch
– Machine wash cold
– Hang to dry
– No dry cleaning needed
– Fabric Content: 88% Polyester, 12% Spandex
Free Shipping
- Free domestic ground shipping on orders with subtotals of $150 or more. Transit times may vary.
- Overnight shipping $30 and express 2-3 day shipping $25 are available at checkout.
Free Returns
- In-person or online
- Returned items must be unworn and unwashed with tags attached
- Not eligible for refund. Exchange or store credit only up to 45 days after date of delivery
- HOLIDAY POLICY: All purchases made after 11/3 are eligible for return until 1/9
Styled With
A recommended pairing from our stylists.
Helmsman Shorts

Get to know
The Leeward Dress Shirt
The original performance fabric dress shirt is still the best on the market. Designed to blend classic style with modern comfort, the Leeward is a shirt you can trust for everyday wear. Lightweight, wrinkle-resistant, machine washable, and moisture-wicking, it’s made to move with you while maintaining a crisp, polished look—all without a trip to the dry cleaners.
The dress shirt you actually want to wear
Built for all occasions, the Leeward redefines what a dress shirt can be. Whether at the office, on the road, or out for the night, it delivers effortless style and all-day wearability.

- Wrinkle Resistant
- Odor Protection
- Moisture-Wicking
- Four-Way Stretch
No reviews available.
Frequently Asked Questions
The Leeward Short Sleeve shirt comes in the same Classic and Trim fits as our long sleeve Leeward styles.
The Leeward Short Sleeve is designed with a modern length that looks great worn untucked for a more relaxed yet still refined look. Check the product description for specific recommendations on each shirt.
The Leeward Short Sleeve shirt features a hidden button-down collar for a put-together look.
Yes. Their wrinkle resistance and easy-care properties make them ideal for travel.
The Leeward Dress Shirt is available in multiple fits, including Classic and Trim. We also offer a Tall length, to suit various preferences.
The Leeward Dress Shirt offers excellent wrinkle resistance, keeping you looking sharp throughout the day. For any initial wrinkles from the packaging, we recommend a gentle wash and then a low tumble dry or light steam to alleviate any wrinkles or creases.
Yes, these shirts are extremely easy to care for. Simply throw them in the wash using cold water and hang dry. If you see small wrinkles feel free to put it in the dryer at low heat to quickly remove them.
Yes. The Leeward Dress Shirt is designed to be worn with a tie, offering a polished, professional look.
Yes. These collared shirts transition effortlessly from professional to casual settings—pair them with dress pants or jeans for a more laid-back style.
