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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

Shop by Category

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

Zegna

Polka Dot Silk Tie

$270

Canali

Neat Pattern Cotton Sport Shirt

$350

Emanuel Berg

Slim-Fit Striped Modern 4-Flex Jersey Cotton Shirt

$222.99$298Save 25%

Canali

Paisley Silk Tie

$137.99$185Save 25%

Anderson's

Weave Stretch Woven Belt

$215

Brunello Cucinelli

Stretch-Cotton Chinos

$695

Canali

Speckled Lyocell Sport Shirt

$375

Zegna

Reversible Leather Enamel Pin-Buckle Belt

$600

Harold

Technical Stretch Woven Belt

$125

Emanuel Berg

Micro Neat Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Zegna

Geometric Jacquard Silk Tie

$270

Canali

Micro Dot Lyocell Sport Shirt

$375

Zegna

Diamond Silk Tie

$270

Canali

Neat Pattern Stretch-Cotton Chevron Sport Shirt

$350

Zegna

Geometric Jacquard Silk Tie

$270

Zegna

Checkered Centoquaranta Twill Sport Shirt

$675

Zegna

Microminiature Geometric Silk Tie

$270

Ferragamo

Reversible Leather Belt

$550

Zegna

Geometric Jacquard Silk Tie

$270

Zegna

Microminiature Geometric Silk Tie

$270

Zegna

Floral Medallion Silk Tie

$270

Emanuel Berg

Checkered Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Zegna

Paisley Houndstooth Silk Tie

$270

Canali

Polka Dot Silk Tie

$195

Zegna

5 Pieghe Floral Medallion Silk Tie

$410

Canali

Solid Linen Sport Shirt

$395

Zegna

Checkered Centoquaranta Twill Sport Shirt

$675

Canali

Floral Lyocell Sport Shirt

$375

Zegna

Microminiature Geometric Silk Tie

$270

Zegna

Geometric Woven Silk Tie

$270

Brunello Cucinelli

Fine Twill Cotton Sport Shirt

$870

Brioni

Paisley Silk Tie

$395

Wolf 1834

Cub Single Watch Winder

$520

Emanuel Berg

Floral Neat Modern 4-Flex Stretch Knit Shirt

$222.99$298Save 25%

Zegna

Mélange Pure Linen Sport Shirt

$675

Zegna

Diamond Silk Tie

$270

Maurizio Baldassari

Textured Jersey Cotton Sport Shirt

$296.99$425Save 30%

Zegna

Polka Dot Silk Tie

$270

Canali

Solid Linen Sport Shirt

$395

Canali

Slim-Fit Striped Dress Shirt

$295.99$395Save 25%

BOSS

Leather Plaque Buckle Belt

$118

Canali

Wide Striped Silk Tie

$185

Zegna

Floral Medallion Silk Tie

$270

Ralph Lauren Purple Label

Super Knit Silk Tie

$295

Canali

Slim-Fit Striped Dress Shirt

$295.99$395Save 25%

Zegna

5 Pieghe Herringbone Paisley Silk Tie

$410

Emanuel Berg

Medallion Modern 4-Flex Stretch Knit Shirt

$298

Brunello Cucinelli

Tonal Stripe Cotton Sport Shirt

$995

Ralph Lauren Purple Label

Purple Label Neat Pattern Silk Tie

$295

Zegna

Jacquard Silk Tie

$270

Canali

Neat Pattern Cotton Sport Shirt

$350

Zegna

Floral Geometric Silk Tie

$270

Zegna

Checkered Centoquaranta Twill Sport Shirt

$675

Canali

Polka Dot Silk Tie

$145.99$195Save 25%

Zegna

Micro Geometric Pure Cotton Sport Shirt

$855

Zegna

Geometric Floral Silk Tie

$410

Prada

Saffiano Leather Emblem Bifold Wallet

$975

Wolf 1834

Axis Single Static Travel Watch Stand

$205

Zegna

5 Pieghe Floral Medallion Silk Tie

$410

Zegna

Geometric Floral Silk Tie

$410

Canali

Slim-Fit Gingham Dress Shirt

$395

Eton

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

$336.99$450Save 25%

Zegna

Mélange Pure Linen Shorts

$890

Emanuel Berg

Medallion Pattern Modern 4-Flex Jersey Cotton Shirt

$298

Zegna

Geometric Woven Silk Tie

$270

Zegna

Jacquard Silk Tie

$410

Zegna

5 Pieghe Floral Medallion Silk Tie

$410

Zegna

5 Pieghe Herringbone Jacquard Silk Tie

$410

Brunello Cucinelli

Fine Twill Cotton Sport Shirt

$870

Ralph Lauren Purple Label

Pindot Satin Silk Tie

$295

Zegna

5 Pieghe Herringbone Jacquard Silk Tie

$410

Brunello Cucinelli

Mélange Easy Fit Sport Shirt

$895

Brioni

Silk Bow Tie

$350

Zegna

Paisley Woven Silk Tie

$410

Ralph Lauren Purple Label

Purple Label Striped Silk Tie

$295

Canali

Floral Lyocell Sport Shirt

$375

Canali

Slim-Fit Geometric Pattern Dress Shirt

$350

Brunello Cucinelli

Textured Linen Shorts

$775

Harold

Knot Cufflinks & Stud Set

$150

Wolf 1834

Axis Triple Watch Roll

$405

Canali

Micro Neat Cotton Sport Shirt

$325

Zegna

5 Pieghe Herringbone Striped Silk Tie

$410

Brioni

Neat Textured Silk Tie

$395

Eton

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

$336.99$450Save 25%

Zegna

Paisley Woven Silk Tie

$410

Zegna

Geometric Jacquard Silk Tie

$270

Brioni

Jacquard Silk Tie

$395

Wolf 1834

British Racing Pebbled Leather Triple Watch Roll

$405

Eton

The Beatles Collection "All Tout Nichts Necesitas" Silk Pocket Square

$120

Zegna

5 Pieghe Herringbone Striped Silk Tie

$410

Wolf 1834

Rocket Module Single Watch Winder

$825

Wolf 1834

Blake Triple Watch Roll With Capsule

$370

Brioni

Abstract Herringbone Silk Tie

$395

Canali

Pasiley Silk Tie

$137.99$185Save 25%

Canali

Floral Cotton Sport Shirt

$350

Zegna

Premium Cotton Utility Overshirt

$1245

Harold

Classic Knot Cufflinks

$95

Brunello Cucinelli

Western Cotton Leisure Fit Overshirt

$1380

Canali

Micro Floral Silk Tie

$145.99$195Save 25%

Harold

Classic Knotted Cufflinks

$95
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.