Sky Crayton Plaid Leeward Dress Shirt

Lavelle Blazer & Pants

Lightweight Fresco Suit Blazer & Pants

Leeward Dress Shirt

Watson Blazer & Suit Pant

Fresco Suit Jacket & Pants

Gift Box

Restocked

Mizzen Man 3

Main Man 3

Embroidery Available

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Highly Rated

No returns

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Returned items must be unworn and unwashed with all tags attached

Not eligible for refund. Exchange or store credit only up to 45 days after date of delivery

Size

Length

Navy Solid Helmsman Chino Pant

29W / Slim / 30L

30W / Slim / 30L

30W / Slim / 32L

31W / Slim / 30L

31W / Slim / 32L

32W / Slim / 30L

32W / Slim / 32L

32W / Slim / 34L

33W / Slim / 30L

33W / Slim / 32L

34W / Slim / 30L

34W / Slim / 32L

34W / Slim / 34L

35W / Slim / 30L

35W / Slim / 32L

36W / Slim / 30L

36W / Slim / 32L

36W / Slim / 34L

38W / Slim / 32L

38W / Slim / 34L

40W / Slim / 32L

38W / Slim / 30L

Brown Solid Leather Belt

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.

Lightweight feel, ideal for year-round wear

Moisture-wicking, breathable, wrinkle-resistant, 4-way stretch

Fabric Content: 88% Polyester, 12% Spandex

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.

Gary

The first (and best) moisture wicking, wrinkle resistant, machine washable dress shirt.

Pink Heather Leeward Long Sleeve Dress Shirt

Blue Cross Print Leeward Long Sleeve Dress Shirt

Navy Aqua Multi Large Plaid Leeward Long Sleeve Dress Shirt

Green Navy Multi Plaid Leeward Long Sleeve Dress Shirt

Light Blue Gingham Leeward Long Sleeve Dress Shirt

White Navy Mini Grid Leeward Long Sleeve Dress Shirt

Black Solid Long Sleeve Dress Shirt

Light Blue Solid Long Sleeve Dress Shirt

White Solid Long Sleeve Dress Shirt

Blue Tonal Check Leeward Long Sleeve Dress Shirt

White Blue Windowpane Leeward Long Sleeve Dress Shirt

White Pink Geo Floral Print Leeward Long Sleeve Dress Shirt

Pink Gray Diamond Print Leeward Long Sleeve Dress Shirt

Navy Pink Dot Print Leeward Long Sleeve Dress Shirt

Deep Cobalt Gingham Leeward Long Sleeve Dress Shirt

Cream Caribou Plaid Leeward Long Sleeve Dress Shirt

Navy Multi Check Leeward Long Sleeve Dress Shirt

Ctrl+Alt+Delete Print Leeward Long Sleeve Dress Shirt

Blue Gold Plaid Leeward Long Sleeve Dress Shirt

Corner Pocket Print Leeward Long Sleeve Dress Shirt

Gray Floral Dot Print Leeward Long Sleeve Dress Shirt

Large Burgundy Plaid Leeward Long Sleeve Dress Shirt

Light Blue Mini Plaid Leeward Long Sleeve Dress Shirt

White Blue Dot Geo Print Leeward Long Sleeve Dress Shirt

White Maritime Blue Plaid Leeward Long Sleeve Dress Shirt

Blueprint Windowpane Leeward Long Sleeve Dress Shirt

Maritime Blue Geo Print Leeward Long Sleeve Dress Shirt

White Navy Windowpane Leeward Long Sleeve Dress Shirt

Micro Chip Geo Print Leeward Long Sleeve Dress Shirt

Set Sail Ipanema Star Print Leeward Long Sleeve Dress Shirt

Capri Breeze Floral Print Leeward Long Sleeve Dress Shirt

Nightshade Windowpane Leeward Long Sleeve Dress Shirt

Bright White Multi Plaid Leeward Long Sleeve Dress Shirt

Provence Multi Plaid Leeward Long Sleeve Dress Shirt

Prairie Sunset Plaid Leeward Long Sleeve Dress Shirt

White Plus Print Long Sleeve Dress Shirt

Lotus Windowpane Leeward Long Sleeve Dress Shirt

White Multi Plaid Leeward Long Sleeve Dress Shirt

Rose Banker Stripe Leeward Long Sleeve Dress Shirt

Bel Air Blue Banker Stripe Leeward Long Sleeve Dress Shirt

Silver Banker Stripe Leeward Long Sleeve Dress Shirt

Blue Lustre Danbury Plaid Leeward Long Sleeve Dress Shirt

White Danbury Plaid Leeward Long Sleeve Dress Shirt

Navy Madison Check Leeward Long Sleeve Dress Shirt

Navy Solid Leeward Long Sleeve Dress Shirt

True Pink Solid Leeward Long Sleeve Dress Shirt

Sky Hampton Plaid Leeward Long Sleeve Dress Shirt

Navy Ludlow Plaid Leeward Long Sleeve Dress Shirt

Sky Ludlow Plaid Leeward Long Sleeve Dress Shirt

Navy Dash Repeat Leeward Long Sleeve Dress Shirt

Deep Sea Oaklawn Plaid Leeward Long Sleeve Dress Shirt

Sage Lexington Plaid Leeward Long Sleeve Dress Shirt

Navy Lexington Plaid Leeward Long Sleeve Dress Shirt

White Ombre Diamond Leeward Long Sleeve Dress Shirt

White Manor Plaid Leeward Long Sleeve Dress Shirt

Sand Ludlow Plaid Leeward No Tuck Long Sleeve Dress Shirt

Bistro Green Dallas Plaid Leeward Long Sleeve Dress Shirt

White Linear Triangle Leeward Long Sleeve Dress Shirt

Garnet Gingham Leeward Long Sleeve Dress Shirt

Black Dallas Plaid Leeward Long Sleeve Dress Shirt

Deep Sea Plus Print Leeward Long Sleeve Dress Shirt

Sage Dot Leeward Long Sleeve Dress Shirt

Sage Multi Gingham Leeward Long Sleeve Dress Shirt

Nile Blue Double Dot Leeward Long Sleeve Dress Shirt

Nickel Madison Check Leeward Long Sleeve Dress Shirt

Rose Filbert Plaid Leeward Long Sleeve Dress Shirt

White Larkin Plaid Leeward Long Sleeve Dress Shirt

Cobalt Stratford Check Leeward Long Sleeve Dress Shirt

Sky Pyramid Leeward Long Sleeve Dress Shirt

Carolina Star Leeward Long Sleeve Dress Shirt

Coastal Fjord Dot Leeward Long Sleeve Dress Shirt

Nile Blue Banker Stripe Leeward Long Sleeve Dress Shirt

Fern Filbert Plaid Leeward Long Sleeve Dress Shirt

Lilac Straton Check Leeward Long Sleeve Dress Shirt

White Baja Plaid Leeward Long Sleeve Dress Shirt

Coastal Fjord Alamo Gingham Leeward Long Sleeve Dress Shirt

Rose Madison Check Leeward Long Sleeve Dress Shirt

Provence Straton Check Leeward Long Sleeve Dress Shirt

White Watershed Plaid Leeward Long Sleeve Dress Shirt

White Polk Plaid Leeward Long Sleeve Dress Shirt

Holly Berry Coastal Plaid Leeward Long Sleeve Dress Shirt

Sky Rodeo Plaid Leeward Long Sleeve Dress Shirt

White Medallion Print Leeward Long Sleeve Dress Shirt

Sky Triangle Geo Leeward Long Sleeve Dress Shirt

Provence Filbert Plaid Leeward Long Sleeve Dress Shirt

Sky Crayton Plaid Leeward Long Sleeve Dress Shirt

White Diamond Texture Leeward Long Sleeve Dress Shirt

Sky Herringbone Leeward Long Sleeve Dress Shirt

White Modern Tattersall Leeward Long Sleeve Dress Shirt

Navy Diamond Leeward Long Sleeve Dress Shirt

Navy Stewart Plaid Leeward Long Sleeve Dress Shirt

White Eric Plaid Leeward Long Sleeve Dress Shirt

Steel Blue Multi Dot Leeward Long Sleeve Dress Shirt

White Hatch Mark Leeward Long Sleeve Dress Shirt

Denim Blue Alamo Gingham Leeward Long Sleeve Dress Shirt

Hunter Green Straton Check Leeward Long Sleeve Dress Shirt

Steel Blue Tonal Texture Leeward Long Sleeve Dress Shirt

Aluminum Joel Plaid Leeward Long Sleeve Dress Shirt

Aluminum Manor Plaid Leeward Long Sleeve Dress Shirt

3X-Large / Classic / Regular

Large / Classic / Regular

Large / Trim / Regular

Large / Trim / Tall

Medium / Classic / Regular

Medium / Trim / Regular

Medium / Trim / Tall

Small / Trim / Regular

X-Large / Classic / Regular

X-Large / Trim / Regular

X-Large / Trim / Tall

XX-Large / Classic / Regular

XX-Large / Trim / Regular