Skip to content

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.

Shop by Price

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

Shop by Category

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

Emanuel Berg

Micro Neat Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Canali

Floral Lyocell Sport Shirt

$375

Canali

Solid Linen Sport Shirt

$395

Maurizio Baldassari

Textured Jersey Cotton Sport Shirt

$296.99$425Save 30%

Zegna

Mélange Pure Linen Sport Shirt

$675

Canali

Speckled Lyocell Sport Shirt

$375

Canali

Solid Linen Sport Shirt

$395

Emanuel Berg

Slim-Fit Striped Modern 4-Flex Jersey Cotton Shirt

$222.99$298Save 25%

Canali

Neat Pattern Stretch-Cotton Chevron Sport Shirt

$350

Brunello Cucinelli

Mélange Linen Sport Shirt

$830

Brunello Cucinelli

Fine Twill Cotton Sport Shirt

$870

Canali

Slim-Fit Striped Dress Shirt

$295.99$395Save 25%

Canali

Micro Dot Lyocell Sport Shirt

$375

Anderson's

Weave Stretch Woven Belt

$215

Brunello Cucinelli

Stretch-Cotton Chinos

$695

Eton

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

$336.99$450Save 25%

Zegna

Checkered Centoquaranta Twill Sport Shirt

$505.99$675Save 25%

Canali

Neat Pattern Cotton Sport Shirt

$350

Canali

Slim-Fit Striped Dress Shirt

$295.99$395Save 25%

Canali

Neat Pattern Cotton Sport Shirt

$350

Canali

Slim-Fit Gingham Dress Shirt

$395

Zegna

Micro Geometric Pure Cotton Sport Shirt

$855

BOSS

Leather Plaque Buckle Belt

$118

Zegna

Checkered Centoquaranta Twill Sport Shirt

$675

Eton

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

$336.99$450Save 25%

Canali

Slim-Fit Geometric Pattern Dress Shirt

$350

Emanuel Berg

Medallion Pattern Modern 4-Flex Jersey Cotton Shirt

$298

Brunello Cucinelli

Tonal Stripe Cotton Sport Shirt

$995

Canali

Floral Lyocell Sport Shirt

$375

Brunello Cucinelli

Fine Twill Cotton Sport Shirt

$870

Prada

Saffiano Leather Emblem Bifold Wallet

$975

Zegna

Checkered Centoquaranta Twill Sport Shirt

$675

Zegna

Mélange Pure Linen Shorts

$890

Emanuel Berg

Medallion Modern 4-Flex Stretch Knit Shirt

$298

Canali

Micro Neat Cotton Sport Shirt

$325

Brunello Cucinelli

Mélange Easy Fit Sport Shirt

$895

Wolf 1834

Cub Single Watch Winder

$520

Wolf 1834

Blake Triple Watch Roll With Capsule

$370

Eton

Elevated Collection Organic Supima Cotton Dress Shirt

$395

Canali

Slim-Fit Neat Dress Shirt

$425

Zegna

Premium Cotton Utility Overshirt

$1245

Brunello Cucinelli

Mélange Linen Sport Shirt

$830

Canali

Jersey Cotton Sport Shirt

$395

Canali

Mini Windowpane Dress Shirt

$295.99$395Save 25%

Canali

Micro Neat Pattern Dress Shirt

$350

Zegna

Reversible Leather Enamel Pin-Buckle Belt

$419.99$600Save 30%

Eton

Contemporary Fit Paisley Shirt

$261.99$350Save 25%

Maurizio Baldassari

Textured Linen Sport Shirt

$325

Canali

Floral Cotton Sport Shirt

$350

Canali

Micro Pattern Dress Shirt

$350

Zegna

Mélange Pure Linen Shorts

$890

Zegna

Cotton-Linen Chino Shorts

$605

Zegna

Two-Tone Reversible Leather Enamel Pin-Buckle Belt

$419.99$600Save 30%

Emanuel Berg

Floral Neat Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Emanuel Berg

Micro Medallion Print Luxury Sport Shirt

$207.99$278Save 25%

Canali

Geometric Cotton Sport Shirt

$350

Eton

Slim Fit Twill Shirt with Geometric Contrast Details

$280

Emanuel Berg

Solid Modern 4-Flex Stretch Cotton Knit Shirt

$298

Emanuel Berg

Checkered Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Canali

Floral Lyocell Sport Shirt

$375

Canali

Micro Pattern Dress Shirt

$350

Prada

Reversible Saffiano Leather Dress Belt

$975

Canali

Pinstripe Dress Shirt

$325

Canali

Slim-Fit Diagonal Pattern Dress Shirt

$280.99$375Save 25%

Brunello Cucinelli

Cotton Denim Shirt

$895

Eton

Slim Fit Mirage Cotton Tencel Shirt

$212.99$285Save 25%

Brunello Cucinelli

Western Cotton Leisure Fit Overshirt

$1380

Zegna

Premium Cotton Utility Overshirt

$1245

Eton

Slim Fit Striped Shirt

$216.99$290Save 25%

Maurizio Baldassari

Plaid Cotton-Linen Sport Shirt

$233.99$335Save 30%

Eton

Slim Fit Striped Shirt

$216.99$290Save 25%

Canali

Short-Sleeve Bengal Stripe Shirt

$375

Emanuel Berg

Check Twill Luxury Sport Shirt

$207.99$278Save 25%

Canali

Multi-Check Dress Shirt

$295.99$395Save 25%

Harold

Knot Cufflinks & Stud Set

$150

Canali

Short-Sleeve Bengal Stripe Shirt

$325

Montblanc

Homage To Vincent Van Gogh Cufflinks

$430

Zegna

Chino Cotton-Linen Shorts

$605

Emanuel Berg

Striped Dobby Button Down Collar Shirt

$222.99$298Save 25%

Emanuel Berg

Striped Cotton-Lyocell Blend Dress Shirt

$298

Zegna

Tonal Reversible Leather Belt

$468.99$670Save 30%

Zegna

Chino Cotton-Linen Shorts

$605

Brunello Cucinelli

Textured Linen Cargo Pants

$1295

Zegna

Suede Triple Stitch Pin-Buckle Belt

$468.99$670Save 30%

Zegna

Grain Leather Reversible Triple Stitch Pin-Buckle Belt

$468.99$670Save 30%

Eton

Contemporary Fit Signature Twill Floral Trim Dress Shirt

$280

Eton

Slim Fit Dotted Micro Check Shirt

$220.99$295Save 25%

Eton

Elevated Collection Pique Dress Shirt

$395

Eton

Contemporary Fit Solid Shirt with Floral Contrast Detail

$280

Eton

Slim Fit Micro Floral Shirt

$295

Emanuel Berg

Mélange Cotton-Lyocell Blend Dress Shirt

$222.99$298Save 25%

Maurizio Baldassari

Textured Linen Sport Shirt

$325

Maurizio Baldassari

Linen Sport Shirt

$325

Montblanc

Sartorial 6CC Bifold Wallet

$545

Ralph Lauren Purple Label

Asford Brushed Poplin Cotton Sport Shirt

$620

Maurizio Baldassari

Striped Linen Sport Shirt

$350

Eton

Contemporary Fit Tonal Print Shirt

$290

L'Objet

Crocodile Playing Cards Box Set Black

$385

Montblanc

Reversible Horseshoe Buckle Belt

$635

Canali

Neat Pattern Dress Shirt

$242.99$325Save 25%
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.