5 Classic Shoes You Could Wear Every Day
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5 Classic Shoes You Could Wear Every Day

The best-heeled men have already entered their loafer era, but that’s not the only old-school style to know right now. Here are five classic options for enhancing your regular looks…
Image: @ghbass_eu

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Pennies

‘Lads in loafers’ is a strong menswear theme. It makes sense to us: a penny loafer is a perfect crossover of casual and formal that can elevate run-of-the-mill looks into pin-sharp outfits.

Stanford Penny Loafers

G.H.Bass
£205

Recanati Loafers

Geox
£119.90

Bill Derby Loafers

John Lobb
£1,700

The Penny Loafers

Morjas
£370

Ruched Loafers

Russell & Bromley
£245

Yuketen Rob's Loafers

Yuketen
£595

Derbies

The derby is the dapper uncle of the traditional shoe family. It’s on the formal side, but is easily built into laid-back office looks and chic weekender outfits to give a dash of elegance. Choose a moc-toe style for a casual approach.

Shannon Derby Shoes

Church's
£980

Apsley Glossed-Leather Derby Shoes

Dunhill
£930

Lis Noir Derby Shoes

Paraboot
$630

Toe Cap Derby Shoes

Russell & Bromley
£225

Woodstock Derby Shoes

Tricker's
£565

Vinnee Leather Derby Shoes

Vinny’s
£260

Boat Shoes

As a like-for-like swap with trainers, boat shoes come close in terms of comfort, dexterity and weight. Style wise, they can add splashes of boho and preppiness.

Princeton Boat Shoes

Schuh
£65

Batto Croc-Effect Suede Boat Shoes

Jacquemeus
£450

Merton Leather Boat Shoes

Ralph Lauren
£179

Authentic Boat Shoes

Timberland
£180

Portland Martellato Shoes

Sebago
£84.15  (were £159)

Barth Shoes

Paraboot
$310

Chelseas

Most boot styles stomp on trainers with their rugged masculinity. With fit, sole and style all working in harmony, a good Chelsea can also compete on comfort with sneakers. 

Boots

Blundstone
£195

Newmarket Full-Grain Leather Chelsea Boots

Edward Green
£1,390

Camion Ankle Boots

Our Legacy
£422

Craftsman Boots

R.H.Willams
£425

Crofton Borg Chelsea Boots

Russell & Bromley
£245

Suede Chelsea Boots

Schuh
£70

Strap/Belt Shoes

Brands are experimenting again with strap and buckle design, using chunkier metals, larger buckles and even adding buckles to styles that have never had them before. The monopoly of the double monk strap is over, and men’s footwear is all the better for it.

Thomas Cap-Toe Leather Monk-Strap Shoes

George Cleverley
£660

Tommy Lug Ebano Grained Shoes

Jacques Solovière
£336.17

Sergio Derby Shoes

Loro Piana
£945

Vadstena Shoes

Myrqvist
£299

Sean Buckled Full-Grain Leather Penny Loafers

Tom Ford
£1,250

Maltby Ruched Loafers

Russell & Bromley
£245

All products on this page have been selected by our editorial team, however we may make commission on some products.

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