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The Classic Gentlemen

While some men cycle through the latest trends, others remain committed to the hallmarks of traditional sophistication. For the Classic Guy, we suggest gifts with long-term investment value.

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Gifts Under $100
Gifts Under $250
Gifts Under $500

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Dress Shirts
Ties & Pocket Squares
Belts
Stationery
Watches
+2 More
756 items

Brunello Cucinelli

Tonal Stripe Cotton Sport Shirt

$596.99$995Save 40%

Canali

Speckled Lyocell Sport Shirt

$280.99$375Save 25%

Canali

Floral Lyocell Sport Shirt

$280.99$375Save 25%

Harold

Knot Cufflinks & Stud Set

$89.99$150Save 40%

Canali

Neat Pattern Stretch-Cotton Chevron Sport Shirt

$261.99$350Save 25%

Eton

Etched Geometric Twill Dress Shirt

$220.99$295Save 25%

Zegna

Checkered Centoquaranta Twill Sport Shirt

$404.99$675Save 40%

Brunello Cucinelli

Fine Twill Cotton Sport Shirt

$521.99$870Save 40%

Canali

Solid Linen Sport Shirt

$295.99$395Save 25%

Emanuel Berg

Modern-Fit Striped Modern 4-Flex Jersey Cotton Shirt

$222.99$298Save 25%

Canali

Neat Pattern Cotton Sport Shirt

$261.99$350Save 25%

Anderson's

Weave Stretch Woven Belt

$215

Prada

Saffiano Leather Emblem Bifold Wallet

$975

Canali

Floral Lyocell Sport Shirt

$280.99$375Save 25%

Maurizio Baldassari

Textured Jersey Cotton Sport Shirt

$211.99$425Save 50%

BOSS

Leather Plaque Buckle Belt

$87.99$118Save 25%

Zegna

Micro Geometric Pure Cotton Sport Shirt

$512.99$855Save 40%

Zegna

Checkered Centoquaranta Twill Sport Shirt

$404.99$675Save 40%

Emanuel Berg

Medallion Pattern Modern 4-Flex Jersey Cotton Shirt

$222.99$298Save 25%

Emanuel Berg

Modern-Fit Floral Patterned Stretch Poplin Luxury Sport Shirt

$207.99$278Save 25%

Canali

Micro Dot Lyocell Sport Shirt

$280.99$375Save 25%

Eton

The Beatles Collection "All You Need Is Love" Printed Cotton Shirt

$336.99$450Save 25%

Eton

The Beatles Collection "All You Need Is Love" Embroidered Twill Shirt

$336.99$450Save 25%

Canali

Slim-Fit Striped Dress Shirt

$236.99$395Save 40%

Canali

Neat Pattern Cotton Sport Shirt

$261.99$350Save 25%

Emanuel Berg

Medallion Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Zegna

Mélange Pure Linen Shorts

$890

Zegna

Checkered Centoquaranta Twill Sport Shirt

$404.99$675Save 40%

Canali

Micro Neat Cotton Sport Shirt

$242.99$325Save 25%

Emanuel Berg

Floral Printed Cotton Dress Shirt

$222.99$298Save 25%

Eton

Martini Signature Poplin Dress Shirt

$220.99$295Save 25%

Maurizio Baldassari

Checkered Cotton-Linen Sport Shirt

$196.99$395Save 50%

Zegna

Chino Cotton-Linen Shorts

$362.99$605Save 40%

Emanuel Berg

Checkered Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Eton

Elevated Collection Organic Supima Cotton Dress Shirt

$295.99$395Save 25%

Eton

Slim Fit Striped Dress Shirt

$205.99$275Save 25%

Zegna

Grain Leather Reversible Triple Stitch Pin-Buckle Belt

$359.99$670Save 46%

Zegna

Cotton-Linen Chino Shorts

$362.99$605Save 40%

Canali

Short-Sleeve Bengal Stripe Shirt

$280.99$375Save 25%

Eton

Slim Fit Micro Neat Dress Shirt

$220.99$295Save 25%

Emanuel Berg

Micro Neat Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Eton

Elevated Collection Bengal Stripe Poplin Dress Shirt

$295.99$395Save 25%

Canali

Pinstripe Dress Shirt

$194.99$325Save 40%

Emanuel Berg

Modern Fit 4-Flex Stretch-Cotton Dress Shirt

$222.99$298Save 25%

Canali

Short-Sleeve Bengal Stripe Shirt

$242.99$325Save 25%

Canali

Slim-Fit Gingham Dress Shirt

$236.99$395Save 40%

Eton

Slim Fit Striped Shirt

$216.99$290Save 25%

Wolf 1834

Blake Triple Watch Roll With Capsule

$370

Ralph Lauren Purple Label

Asford Brushed Poplin Cotton Sport Shirt

$371.99$620Save 40%

Emanuel Berg

Modern-Fit Patterned Stretch-Poplin Luxury Sport Shirt

$207.99$278Save 25%

Zegna

Reversible Leather Enamel Pin-Buckle Belt

$335.99$600Save 44%

Zegna

Mélange Pure Linen Shorts

$890

Brunello Cucinelli

Stretch-Cotton Chinos

$695

Maurizio Baldassari

Plaid Cotton-Linen Sport Shirt

$166.99$335Save 50%

Canali

Floral Cotton Sport Shirt

$261.99$350Save 25%

Canali

Multi-Check Dress Shirt

$295.99$395Save 25%

Canali

Slim-Fit Geometric Pattern Dress Shirt

$209.99$350Save 40%

Eton

Contemporary Fit Solid Shirt with Floral Contrast Detail

$209.99$280Save 25%

Emanuel Berg

Solid Modern 4-Flex Stretch Cotton Knit Shirt

$222.99$298Save 25%

Zegna

Suede Triple Stitch Pin-Buckle Belt

$359.99$670Save 46%

Canali

Slim-Fit Diagonal Pattern Dress Shirt

$280.99$375Save 25%

Canali

Micro Pattern Dress Shirt

$261.99$350Save 25%

Canali

Slim-Fit Striped Dress Shirt

$295.99$395Save 25%

Emanuel Berg

Striped Cotton-Lyocell Blend Dress Shirt

$222.99$298Save 25%

Eton

Slim Fit Mirage Cotton Tencel Shirt

$212.99$285Save 25%

Eton

Slim Fit Striped Shirt

$216.99$290Save 25%

Canali

Jersey Cotton Sport Shirt

$295.99$395Save 25%

Wolf 1834

Cub Single Watch Winder

$520

Eton

Elevated Collection Organic Supima Cotton Dress Shirt

$295.99$395Save 25%

Eton

Pasiley Cotton-Tencel Shirt

$220.99$295Save 25%

Eton

Elevated Collection Check Poplin Dress Shirt

$295.99$395Save 25%

Zegna

Premium Cotton Utility Overshirt

$746.99$1245Save 40%

Emanuel Berg

Micro Medallion Print Luxury Sport Shirt

$207.99$278Save 25%

Brunello Cucinelli

Mélange Linen Sport Shirt

$497.99$830Save 40%

Eton

Slim Fit Twill Shirt with Geometric Contrast Details

$209.99$280Save 25%

Zegna

Tonal Reversible Leather Belt

$353.99$670Save 47%

Canali

Micro Neat Pattern Dress Shirt

$261.99$350Save 25%

Emanuel Berg

Striped Dobby Button Down Collar Shirt

$222.99$298Save 25%

Zegna

Two-Tone Reversible Leather Enamel Pin-Buckle Belt

$335.99$600Save 44%

Eton

Slim Fit Floral Print Shirt

$220.99$295Save 25%

Brunello Cucinelli

Western Cotton Leisure Fit Overshirt

$827.99$1380Save 40%

Maurizio Baldassari

Striped Linen Sport Shirt

$261.99$350Save 25%

Canali

Slim-Fit Neat Dress Shirt

$317.99$425Save 25%

Eton

Slim Fit Micro Floral Shirt

$220.99$295Save 25%

Wolf 1834

Roadster Pebbled Vegan Leather Triple Watch Roll

$370

L'Objet

Crocodile Playing Cards Box Set Black

$385

Eton

Contemporary Fit Paisley Shirt

$261.99$350Save 25%

Eton

Slim Fit Dotted Micro Check Shirt

$220.99$295Save 25%

Zegna

Triple Stitch Suede Pin-Buckle Belt

$401.99$670Save 40%

Tateossian

Giza Beaded Snowflake Obsidian Bracelet

$250

Emanuel Berg

Check Twill Luxury Sport Shirt

$207.99$278Save 25%

Montblanc

The Origin Collection Meisterstück Cufflinks

$380

Canali

Neat Pattern Dress Shirt

$242.99$325Save 25%

Giorgio Armani

Bermuda Canvas Shorts

$1695

Montblanc

Reversible Horseshoe Buckle Belt

$635

Eton

Contemporary Fit Signature Twill Floral Trim Dress Shirt

$209.99$280Save 25%

Eton

Elevated Collection Pique Dress Shirt

$295.99$395Save 25%

100 Hands

Gold Line Solid Oxford Shirt

$389.99$650Save 40%

Brunello Cucinelli

Garment-Dyed Western Denim Shirt

$716.99$1195Save 40%

L'Objet

Large Swan Bowl Black

$916.99$1310Save 30%
Fashions are ephemeral, however, not every man subscribes to the idea of a complete wardrobe reinvention every year. For these Timeless Gentlemen, we suggest investment pieces like a classic cableknit sweater, a handsome cigar cutter, a sleek stainless-steel watch, or a luxe leather-cased flask.