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Trim Fit

Trim Fit

A tailored look right off the rack, the trim fit is designed with a tapered waist for a modern silhouette and is available in all sizes. If you want to feel comfortable while still looking sharp, this is your style.

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    Light Blue Mini Gingham Product Light Blue Mini Gingham Close-up/Swatch

    Monaco Dress Shirt Light Blue Mini Gingham $128

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    Blue and Aqua Check Product Blue and Aqua Check Close-up/Swatch

    Monaco Dress Shirt Blue and Aqua Check $128

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    Navy Large Plaid Product Navy Large Plaid Close-up/Swatch

    Monaco Dress Shirt Navy Large Plaid $128

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    Teal Large Plaid Product Teal Large Plaid Close-up/Swatch

    Leeward Antimicrobial Dress Shirt Teal Large Plaid $128

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    Purple Gray Gingham Check Product Purple Gray Gingham Check Close-up/Swatch

    Leeward Antimicrobial Dress Shirt Purple Gray Gingham Check $128

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    Light Blue Mini Check Product Light Blue Mini Check Close-up/Swatch

    Leeward No Tuck Dress Shirt Light Blue Mini Check $128

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    Navy & White Windowpane Product Navy & White Windowpane Close-up/Swatch

    Leeward No Tuck Dress Shirt Navy & White Windowpane $128

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    Purple Navy Large Check Product Purple Navy Large Check Close-up/Swatch

    Leeward Antimicrobial Dress Shirt Purple Navy Large Check $128

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    Purple Camo Product Purple Camo Close-up/Swatch

    Versa Polo Purple Camo $78

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    White Camo Product White Camo Close-up/Swatch

    Versa Polo White Camo $78

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    Navy and Blue Contrast Product Navy and Blue Contrast Close-up/Swatch

    EasyKnit Henley Navy and Blue Contrast $78

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    Charcoal Heather Product Charcoal Heather Close-up/Swatch

    EasyKnit Henley Charcoal Heather $78

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    Navy Heather Product Navy Heather Close-up/Swatch

    EasyKnit Henley Navy Heather $78

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    Light Blue Gray Check Product Light Blue Gray Check Close-up/Swatch

    Leeward No Tuck Dress Shirt Light Blue Gray Check $128

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    Navy Printed Stripe Product Navy Printed Stripe Close-up/Swatch

    Leeward Short Sleeve Navy Printed Stripe $88

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    Chambray Stripe Print Product Chambray Stripe Print Close-up/Swatch

    Leeward Short Sleeve Chambray Stripe Print $88

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    Navy Gray Gingham Check Product Navy Gray Gingham Check Close-up/Swatch

    City Flannel Navy Gray Gingham Check $125

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    Navy Gray Gingham Check Product Navy Gray Gingham Check Close-up/Swatch

    Leeward No Tuck Dress Shirt Navy Gray Gingham Check $128

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    Burgundy Green Large Windowpane Product Burgundy Green Large Windowpane Close-up/Swatch

    Leeward No Tuck Dress Shirt Burgundy Green Large Windowpane $128

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    Rust Navy Large Windowpane Product Rust Navy Large Windowpane Close-up/Swatch

    Leeward No Tuck Dress Shirt Rust Navy Large Windowpane $128

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    Hunter Green Check Product Hunter Green Check Close-up/Swatch

    Leeward No Tuck Dress Shirt Hunter Green Check $128

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    Green Navy Star Diamond Product Green Navy Star Diamond Close-up/Swatch

    Leeward No Tuck Dress Shirt Green Navy Star Diamond $128

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    Navy Red Multi Large Plaid Product Navy Red Multi Large Plaid Close-up/Swatch

    City Flannel Navy Red Multi Large Plaid $125

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    Navy Heather Product Navy Heather Close-up/Swatch

    City Flannel Navy Heather $125

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    Gray Multi Plaid Product Gray Multi Plaid Close-up/Swatch

    City Flannel Gray Multi Plaid $125

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    Burgundy Check Product Burgundy Check Close-up/Swatch

    City Flannel Burgundy Check $125

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    Solid Gray Product Solid Gray Close-up/Swatch

    Leeward No Tuck Dress Shirt Solid Gray $128

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    Navy Horizontal Stripe Product Navy Horizontal Stripe Close-up/Swatch

    City Flannel Navy Horizontal Stripe $125

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    Burgundy Navy Large Plaid Product Burgundy Navy Large Plaid Close-up/Swatch

    Leeward Antimicrobial Dress Shirt Burgundy Navy Large Plaid $125

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    Navy Burgundy Horizontal Stripe Product Navy Burgundy Horizontal Stripe Close-up/Swatch

    Leeward No Tuck Dress Shirt Navy Burgundy Horizontal Stripe $128

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    Red Navy Floral Print Product Red Navy Floral Print Close-up/Swatch

    Versa Polo Red Navy Floral Print $78

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    Red Navy Chevron Print Product Red Navy Chevron Print Close-up/Swatch

    Versa Polo Red Navy Chevron Print $78

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    Gray Navy Engineered Stripe Product Gray Navy Engineered Stripe Close-up/Swatch

    Versa Polo Gray Navy Engineered Stripe $78

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    Light Blue Check Product Light Blue Check Close-up/Swatch

    Leeward Dress Shirt Light Blue Check $125

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    Black White Floral Print Product Black White Floral Print Close-up/Swatch

    Leeward Dress Shirt Black White Floral Print $125

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    Light Gray Heather Product Light Gray Heather Close-up/Swatch

    drirelease® Long Sleeve Polo Light Gray Heather $98

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    Navy Heather Product Navy Heather Close-up/Swatch

    drirelease® Long Sleeve Polo Navy Heather $98

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    Burgundy Heather Product Burgundy Heather Close-up/Swatch

    drirelease® Long Sleeve Polo Burgundy Heather $79 $98

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    Gray Double Stripe Product Gray Double Stripe Close-up/Swatch

    Clubhouse Polo Gray Double Stripe $78

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    Navy Red Stripe Product Navy Red Stripe Close-up/Swatch

    Clubhouse Polo Navy Red Stripe $78

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    Blue Red Multi Plaid Product Blue Red Multi Plaid Close-up/Swatch

    Lightweight Leeward Dress Shirt Blue Red Multi Plaid $75 $88

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    Navy And Red Madras Product Navy And Red Madras Close-up/Swatch

    Leeward Short Sleeve Navy And Red Madras $75 $88

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    Navy And Sea Green Floral Print Product Navy And Sea Green Floral Print Close-up/Swatch

    Leeward Short Sleeve Navy And Sea Green Floral Print $75 $88

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    Navy Red Mini Check Product Navy Red Mini Check Close-up/Swatch

    Lightweight Leeward Short Sleeve Navy Red Mini Check $65 $78

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    Red And Navy Arrow Print Product Red And Navy Arrow Print Close-up/Swatch

    Lightweight Leeward Dress Shirt Red And Navy Arrow Print $75 $88

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    Navy Solid Product Navy Solid Close-up/Swatch

    Phil Mickelson Polo Navy Solid $78

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    Aqua And Navy Dot Print Product Aqua And Navy Dot Print Close-up/Swatch

    Phil Mickelson Polo Aqua And Navy Dot Print $78

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    Navy And Bel Air Blue Multi Plaid Product Navy And Bel Air Blue Multi Plaid Close-up/Swatch

    Lightweight Leeward Dress Shirt Navy And Bel Air Blue Multi Plaid $75 $88

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    Gray Stripe Product Gray Stripe Close-up/Swatch

    Wilson Long Sleeve Polo Gray Stripe $55 $78

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    Navy Grid Product Navy Grid Close-up/Swatch

    Leeward Popover Navy Grid $50 $98

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    Navy Solid Product Navy Solid Close-up/Swatch

    Wilson Long Sleeve Polo Navy Solid $55 $78

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    Cobalt Blue And Pink Multi Check Product Cobalt Blue And Pink Multi Check Close-up/Swatch

    Leeward Dress Shirt Cobalt Blue And Pink Multi Check $99 $125

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    Light Blue Solid Product Light Blue Solid Close-up/Swatch

    Wilson Long Sleeve Polo Light Blue Solid $55 $78

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    Navy And White Horizontal Stripe Product Navy And White Horizontal Stripe Close-up/Swatch

    Wilson Polo Navy And White Horizontal Stripe $55 $68

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    Navy Large Windowpane Product Navy Large Windowpane Close-up/Swatch

    Leeward Dress Shirt Navy Large Windowpane $99 $125

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    Red Navy Check Product Red Navy Check Close-up/Swatch

    Leeward Dress Shirt Red Navy Check $99 $125

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    Navy Gray Dot Print Product Navy Gray Dot Print Close-up/Swatch

    Leeward Dress Shirt Navy Gray Dot Print $99 $125

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    Black Gray Gingham Product Black Gray Gingham Close-up/Swatch

    Leeward Dress Shirt Black Gray Gingham $99 $125

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    Light Gray Heather Product Light Gray Heather Close-up/Swatch

    Arden Sweater Light Gray Heather $165 $198

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    Red Heather Product Red Heather Close-up/Swatch

    Wilson Polo Red Heather $55 $68

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    Navy Contrast Collar Product Navy Contrast Collar Close-up/Swatch

    Wilson Long Sleeve Polo Navy Contrast Collar $55 $78

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    Light Gray Heather Product Light Gray Heather Close-up/Swatch

    Wilson Long Sleeve Polo Light Gray Heather $55 $78

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    Blue Pink Glen Plaid Product Blue Pink Glen Plaid Close-up/Swatch

    Leeward Dress Shirt Blue Pink Glen Plaid $99 $125

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    Navy Red Mini Check Product Navy Red Mini Check Close-up/Swatch

    Lightweight Leeward Dress Shirt Navy Red Mini Check $75 $88

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    Niagara Multi Check Product Niagara Multi Check Close-up/Swatch

    Leeward Dress Shirt Niagara Multi Check $99 $125

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    Navy Red Check Product Navy Red Check Close-up/Swatch

    Leeward Dress Shirt Navy Red Check $99 $125

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    Navy Blue Tattersall Product Navy Blue Tattersall Close-up/Swatch

    Leeward Dress Shirt Navy Blue Tattersall $99 $125

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    Navy Red Multi Plaid Product Navy Red Multi Plaid Close-up/Swatch

    Leeward Dress Shirt Navy Red Multi Plaid $89 $125

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    Red White Mini Floral Print Product Red White Mini Floral Print Close-up/Swatch

    Leeward Short Sleeve Red White Mini Floral Print $75 $105

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    Blue Multi Check Product Blue Multi Check Close-up/Swatch

    Leeward Dress Shirt Blue Multi Check $125

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    Red Navy Gingham Product Red Navy Gingham Close-up/Swatch

    Leeward Dress Shirt Red Navy Gingham $99 $125

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    Red Blue Check Product Red Blue Check Close-up/Swatch

    Leeward Dress Shirt Red Blue Check $125

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    Blue Large Multi Check Product Blue Large Multi Check Close-up/Swatch

    Lightweight Leeward Short Sleeve Blue Large Multi Check $65 $80

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    Navy White Check Product Navy White Check Close-up/Swatch

    Lightweight Leeward Dress Shirt Navy White Check $75 $88

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    Blue Orange Check Product Blue Orange Check Close-up/Swatch

    Lightweight Leeward Dress Shirt Blue Orange Check $75 $88

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    Red Blue Pink Multi Plaid Product Red Blue Pink Multi Plaid Close-up/Swatch

    Leeward Dress Shirt Red Blue Pink Multi Plaid $89 $125

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    Navy Diamond Geo Print Product Navy Diamond Geo Print Close-up/Swatch

    Leeward Dress Shirt Navy Diamond Geo Print $89 $125

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    Orange Blue Multi Check Product Orange Blue Multi Check Close-up/Swatch

    Leeward Dress Shirt Orange Blue Multi Check $89 $125

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    Blue Aqua Check Product Blue Aqua Check Close-up/Swatch

    Leeward Dress Shirt Blue Aqua Check $89 $125

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    Red Light Blue Multi Check Product Red Light Blue Multi Check Close-up/Swatch

    Leeward Dress Shirt Red Light Blue Multi Check $99 $125

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    Floral Stripe Print Product Floral Stripe Print Close-up/Swatch

    Leeward Dress Shirt Floral Stripe Print $89 $125

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    Pink Blue Mini Check Product Pink Blue Mini Check Close-up/Swatch

    Leeward Dress Shirt Pink Blue Mini Check $99 $125

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    Navy Diamond Print Product Navy Diamond Print Close-up/Swatch

    Leeward Dress Shirt Navy Diamond Print $99 $125

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    Navy White Dot Print Product Navy White Dot Print Close-up/Swatch

    Spinnaker Short Sleeve Navy White Dot Print $88

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    Aqua Blue Tattersall Product Aqua Blue Tattersall Close-up/Swatch

    Leeward Dress Shirt Aqua Blue Tattersall $69 $125

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    Aqua Gingham Product Aqua Gingham Close-up/Swatch

    Leeward Dress Shirt Aqua Gingham $89 $125

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    Light Blue Square Print Product Light Blue Square Print Close-up/Swatch

    Leeward Dress Shirt Light Blue Square Print $69 $125

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    Navy Floral Print Product Navy Floral Print Close-up/Swatch

    Leeward Dress Shirt Navy Floral Print $89 $125

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    White Solid Product White Solid Close-up/Swatch

    Leeward Dress Shirt White Solid $125

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    Black Solid Product Black Solid Close-up/Swatch

    Leeward Dress Shirt Black Solid $125

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    White Solid Product White Solid Close-up/Swatch

    Leeward Formal Dress Shirt White Solid $125

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    White Solid Product White Solid Close-up/Swatch

    Leeward Tux Dress Shirt White Solid $135

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    Light Blue Mini Check Product Light Blue Mini Check Close-up/Swatch

    Leeward Formal Dress Shirt Light Blue Mini Check $125

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    Light Blue Gingham Product Light Blue Gingham Close-up/Swatch

    Leeward Dress Shirt Light Blue Gingham $125

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    Navy Grid Product Navy Grid Close-up/Swatch

    Leeward Dress Shirt Navy Grid $125

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    Gray Mini Gingham Product Gray Mini Gingham Close-up/Swatch

    Spinnaker Dress Shirt Gray Mini Gingham $98

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    White Herringbone Product White Herringbone Close-up/Swatch

    Spinnaker Dress Shirt White Herringbone $98

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    Blue Mini Gingham Product Blue Mini Gingham Close-up/Swatch

    Spinnaker Dress Shirt Blue Mini Gingham $98

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    Black Solid Product Black Solid Close-up/Swatch

    Leeward Short Sleeve Black Solid $88

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    Navy Aqua Multi Check Product Navy Aqua Multi Check Close-up/Swatch

    Leeward Dress Shirt Navy Aqua Multi Check $89 $125

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    Navy Gray Geo Print Product Navy Gray Geo Print Close-up/Swatch

    Leeward Dress Shirt Navy Gray Geo Print $89 $125

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    Navy Orange Multi Check Product Navy Orange Multi Check Close-up/Swatch

    Leeward Dress Shirt Navy Orange Multi Check $89 $125

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    Dark Blue Windowpane Product Dark Blue Windowpane Close-up/Swatch

    Leeward Dress Shirt Dark Blue Windowpane $125

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    Light Gray Solid Product Light Gray Solid Close-up/Swatch

    Cunningham Dress Shirt Light Gray Solid $89 $135

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    White Herringbone Product White Herringbone Close-up/Swatch

    2019 Spinnaker Dress Shirt White Herringbone $79 $125

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    Navy Diamond Print Product Navy Diamond Print Close-up/Swatch

    Leeward Dress Shirt Navy Diamond Print $79 $125

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    Purple Green Check Product Purple Green Check Close-up/Swatch

    Leeward Dress Shirt Purple Green Check $79 $125

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    Navy Blue Product Navy Blue Close-up/Swatch

    Lavelle Blazer Navy Blue $298 $350

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    Navy Paisley Print Product Navy Paisley Print Close-up/Swatch

    Leeward Dress Shirt Navy Paisley Print $79 $125

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    Navy Gray Check Product Navy Gray Check Close-up/Swatch

    Leeward Dress Shirt Navy Gray Check $99 $125

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    Charcoal Heather Product Charcoal Heather Close-up/Swatch

    Rockwell Vest Charcoal Heather $99 $125

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    Navy Rounded Square Print Product Navy Rounded Square Print Close-up/Swatch

    Leeward Dress Shirt Navy Rounded Square Print $79 $125

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    Navy White Mini Gingham Product Navy White Mini Gingham Close-up/Swatch

    Leeward Dress Shirt Navy White Mini Gingham $89 $125

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    Purple Blue Multi Check Product Purple Blue Multi Check Close-up/Swatch

    Leeward Dress Shirt Purple Blue Multi Check $79 $125

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    Navy Light Blue Tattersall Product Navy Light Blue Tattersall Close-up/Swatch

    Leeward Dress Shirt Navy Light Blue Tattersall $69 $125

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    Red Blue Mini Check Product Red Blue Mini Check Close-up/Swatch

    Leeward Dress Shirt Red Blue Mini Check $79 $125

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    Red Blue Tattersall Product Red Blue Tattersall Close-up/Swatch

    Leeward Dress Shirt Red Blue Tattersall $99 $125

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    Blue Multi Plaid Product Blue Multi Plaid Close-up/Swatch

    Leeward Short Sleeve Blue Multi Plaid $75 $105

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    Blue Multi Plaid Product Blue Multi Plaid Close-up/Swatch

    Leeward Dress Shirt Blue Multi Plaid $79 $125

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    Blue Chambray Plaid Product Blue Chambray Plaid Close-up/Swatch

    Leeward Dress Shirt Blue Chambray Plaid $99 $125

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    Navy Houndstooth Check Product Navy Houndstooth Check Close-up/Swatch

    Textured Dress Shirt Navy Houndstooth Check $79 $135

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    Light Blue Check Product Light Blue Check Close-up/Swatch

    Leeward Dress Shirt Light Blue Check $79 $125

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    Blue Tattersall Product Blue Tattersall Close-up/Swatch

    Leeward Dress Shirt Blue Tattersall $79 $125

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    Light Blue Glen Plaid Product Light Blue Glen Plaid Close-up/Swatch

    Leeward Textured Dress Shirt Light Blue Glen Plaid $59 $135

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    Navy Red and White Arrow Print Product Navy Red and White Arrow Print Close-up/Swatch

    Leeward Short Sleeve Navy Red and White Arrow Print $75 $105

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    Black Blue Multi Check Product Black Blue Multi Check Close-up/Swatch

    Leeward Dress Shirt Black Blue Multi Check $99 $125

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    Blue and White Windowpane Product Blue and White Windowpane Close-up/Swatch

    Leeward Formal Dress Shirt Blue and White Windowpane $79 $145

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    White Solid Product White Solid Close-up/Swatch

    2019 Leeward Formal Dress Shirt White Solid $99 $125

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    Solid Blue Product Solid Blue Close-up/Swatch

    2019 Leeward Formal Dress Shirt Solid Blue $99

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    Blue Gingham Product Blue Gingham Close-up/Swatch

    2019 Spinnaker Dress Shirt Blue Gingham $79 $125

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