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Brooks Brothers Classic Leather Penny Loafer

Gilt

Brooks Brothers Classic Leather Penny Loafer

$248 $85

At Gilt

About the brand: Classic designs that marry style and function. Classic Leather Penny Loafer in dark red Classic penny loafers, made from calfskin leather. Leather sole. Leather lining. Tone-on-tone stitching. Leather Imported. Buy from Gilt
Quincy Leather Sandals - Mens - Tan

Grenson

Quincy Leather Sandals - Mens - Tan

$184

At Matchesfashion.com

Grenson - Grenson draws inspiration from traditional fisherman's sandals to create this brown Quincy pair. They're crafted from hand-painted leather with robust interlocking straps and a slim logo-debossed sole, then set on a small stacked heel.. Buy from MATCHESFASHION.COM
Dandelion Metallic Loafers - Mens - Black

Christian Louboutin

Dandelion Metallic Loafers - Mens - Black

$795

At Matchesfashion.com

Christian Louboutin - Tap Christian Louboutin's opulent aesthetic with these black Lurex Dandelion loafers. They're expertly made in Italy with grosgrain trim, a beige leather lining and smooth sole coloured in signature red. Team them with sharp suiting.. Buy from MATCHESFASHION.COM
Gucci Horsebit Suede Loafer

Gilt

Gucci Horsebit Suede Loafer

$750 $650

At Gilt

About the brand: Eclectic and coveted. Italian luxury redefined. Please note: Size selections are UK. For US conversions, please reference size chart. Made in Italy Horsebit Suede Loafer in brown suede with light fine gold hardware, horsebit detail and red and green signature webbing detail Lightly padded leather insole Smooth leather sole Our products are 100% genuine. In some cases we purchase merchandise from trusted independent suppliers and not directly from the brand owner. In all cases we stand by the authenticity of every product sold on our site.. Buy from Gilt
Hamptons Collapsible-heel Suede Penny Loafers - Mens - Olive Green

ManebÍ

Hamptons Collapsible-heel Suede Penny Loafers - Mens - Olive Green

$145

At Matchesfashion.com

Manebí - Manebí's khaki-green suede Hamptons loafers are a laid-back interpretation of the heritage silhouette that originated in the 1930s. They're made in Spain by local artisans, with a penny bar strap and collapsible heel, then set on a braided jute midsole and a beige rubber sole.. Buy from MATCHESFASHION.COM
Arizona Oiled-leather Sandals - Mens - Yellow Gold

Birkenstock

Arizona Oiled-leather Sandals - Mens - Yellow Gold

$91

At Matchesfashion.com

Birkenstock - Birkenstock updates the iconic Arizona sandals with this dark yellow pair, made from oiled leather - untreated hide with a unique, natural finish. They're crafted in the label's native Germany and have two buckled straps with antiqued-gold hardware for a vintage look, then are set on an EVA-cushioned footbed.. Buy from MATCHESFASHION.COM
Leather Sneakers - White

Both

Leather Sneakers - White

$220 $110

At Net-a-porter

EXCLUSIVE AT NET-A-PORTER. Despite only launching in 2017, both's founders have 30 years of experience developing methods of working with rubber - which you can see in the refined ribbed soles of these sneakers. They're made from smooth white leather and minimally detailed, so they'll work with lots of pieces you already have in your closet.. Buy from Net-A-Porter
Suede Espadrille Boots - Mens - Brown

Saint Laurent

Suede Espadrille Boots - Mens - Brown

$445

At Matchesfashion.com

Saint Laurent - Saint Laurent's brown boots are set on a braided jute espadrille sole that's handcrafted by Spanish artisans. They're made from brushed suede that's hallmarked with a black and gold leather logo at the heel. Wear them with shirts and jeans in the warmer months.. Buy from MATCHESFASHION.COM
Lace-up Suede Deck Shoes - Mens - Brown

Brunello Cucinelli

Lace-up Suede Deck Shoes - Mens - Brown

$795

At Matchesfashion.com

Brunello Cucinelli - Brunello Cucinelli's brown deck shoes are inspired by traditional nautical styles and have a flat, rubber sole, originally designed to provide grip on a wet surface without damaging the boat. Crafted in Italy, they have a supple suede upper with a topstitched vamp and leather laces threaded around the outside edge.. Buy from MATCHESFASHION.COM
Wesper Leather B-Chain Bit Loafers

Bally

Wesper Leather B-Chain Bit Loafers

$625 $406

At Bergdorf Goodman

Bally "Wesper" loafers in calf leather. Stacked heel. Round toe. Notched vamp. B-chain bit strap. Slip-on style. Made in Switzerland.. Buy from Bergdorf Goodman
THICK-SOLED LEATHER SNEAKERS

Cos

THICK-SOLED LEATHER SNEAKERS

$135

At Cos

These lace-up sneakers are made from panels of smooth leather with thick rubber soles. A classic style, they feature waxed cotton laces, leather toe caps and they are finished with contrasting-coloured linings. Sole width: 1¼". Buy from COS
Classic Canvas Loafers - Mens - Black

Rivieras

Classic Canvas Loafers - Mens - Black

$78

At Matchesfashion.com

Rivieras - Rivieras' black canvas Classic loafers signal the label's laid-back aesthetic. Crafted in Spain on a textured rubber sole, they're trimmed in braided accents and have a soft terry interior for comfort.. Buy from MATCHESFASHION.COM
Donald Pliner Parson Oxford

Gilt

Donald Pliner Parson Oxford

$235 $100

At Gilt

Color/material: blue textile Lace-up closure Lightly padded insole Man-made sole Imported. Buy from Gilt
Dandelion Abstract Cutout Metallic Slip-On Shoes

Christian Louboutin

Dandelion Abstract Cutout Metallic Slip-On Shoes

$795

At Bergdorf Goodman

Christian Louboutin "Dandelion" abstract cutout pattern loafers in metallic fabric. Stacked heel. Round toe. Notched vamp. Slip-on style. Made in Italy.. Buy from Bergdorf Goodman
Greggo Leather Oxford Shoes - Mens - Black

Christian Louboutin

Greggo Leather Oxford Shoes - Mens - Black

$895

At Matchesfashion.com

Christian Louboutin - Christian Louboutin's black suede Greggo Oxford shoes are offset with textured panels for a modern riff of a traditional British menswear silhouette. Crafted in Italy, they're joined with curved woven panels and offset with a leather toecap, then finished with the label's signature red lacquered soles. Choose them to bring an alternative finish to tailored separates.. Buy from MATCHESFASHION.COM
Frond-print Cotton-canvas Trainers - Mens - Green Multi

Amiri

Frond-print Cotton-canvas Trainers - Mens - Green Multi

$550 $275

At Matchesfashion.com

Amiri - Impart an artistic sensibility to your off-duty looks with Amiri's ivory trainers, which have a cotton-canvas upper that's patterned with illustrative palm fronds. Fitted with a lace-up oxford vamp, they're set on a textured rubber sole and hallmarked with the label's logo at the leather heel panel.. Buy from MATCHESFASHION.COM
LEATHER HIGH TOP SNEAKERS

Cos

LEATHER HIGH TOP SNEAKERS

$150

At Cos

Forever footwear. Made from cow nappa, the carefully constructed upper is set on an oversized plain sole making them a minimal addition to your trainer rotation. - Nappa upper - Flat eyelets - Flat waxed cotton laces - Plain rubber sole - Stitching detail Shell: 100% Cow nappa, Sole: 100% Thermoplastic rubber. Buy from COS
Hs1-s Tarther Blast Running Trainers - Mens - Blue Multi

Asics

Hs1-s Tarther Blast Running Trainers - Mens - Blue Multi

$124

At Matchesfashion.com

Asics - ASICS combines heritage silhouettes with modern technology to create these navy HS1-S Tarther Blast trainers, which are crafted using recycled materials. They're made with panels of faux leather and faux suede with an embroidered logo to the heel and rest on a FLYTEFOAM™ Blast midsole, which give them a cushioned feel.. Buy from MATCHESFASHION.COM
Boulder Driving Loafer

Allen Edmonds

Boulder Driving Loafer

$245 $100

At Nordstrom

A smart mudguard styles an unlined, moccasin-toe loafer hand-sewn with a durable rubber sole, a slightly squared-off toe and an elongated front for added comfort. Allen Edmonds has been making shoes in America for nearly 100 years using fine leathers, a 212-stepcrafting process and 360 degree Goodyear welt construction to ensure a high-quality product, every time. Style Name: Allen Edmonds Boulder Driving Loafer (Men). Style Number: 291321.. Buy from Nordstrom
Westbury Monk-strap Leather Shoes - Mens - Black

Church's

Westbury Monk-strap Leather Shoes - Mens - Black

$574

At Matchesfashion.com

Church's - These black Westbury shoes from Church's are characterised by a single monk strap, which first appeared on footwear during the 15th century. They're crafted in the UK from polished leather to an almond-toe shape with a silver buckle and small stacked heel for a sophisticated finish.. Buy from MATCHESFASHION.COM
Leather Derby Brogues - Mens - Black

Brioni

Leather Derby Brogues - Mens - Black

$975

At Matchesfashion.com

Brioni - Underscore looks with Brioni's black brogues for a timeless air. Hand crafted by artisans in Italy from smooth leather, they have classic Derby quarters that secure with laces and a streamlined Blake-stitched sole.. Buy from MATCHESFASHION.COM
M by Bruno Magli Barni Leather Oxford

Gilt

M by Bruno Magli Barni Leather Oxford

$460 $180

At Gilt

Color/material: dark grey leather Design details: perforated detailing Lace-up closure Lightly padded leather insole Smooth man-made sole with light traction 1in heel Please note: All measurements are approximate and were taken from a size 9; slight variations may occur. Made in Italy. Buy from Gilt
1461 Lace-up Leather Derby Shoes - Mens - Black

Dr. Martens

1461 Lace-up Leather Derby Shoes - Mens - Black

$130

At Matchesfashion.com

Dr. Martens - Dr. Martens's signature black 1461 Derby shoes are modelled on an archived style that was first introduced in the 1960s. They're crafted from smooth leather with lace-up eyelets and a Goodyear-welted midsole accented by orange topstitching, then set on a chunky rubber sole.. Buy from MATCHESFASHION.COM
'Sea Kite' Boat Shoe

Sperry

'Sea Kite' Boat Shoe

$110

At Nordstrom

Classic boat shoe styling and state-of-the-art sneaker design team up to create a high-performance hybrid that's breathable, supportive and stylish all at once. Style Name: Sperry 'Sea Kite' Boat Shoe. Style Number: 953813.. Buy from Nordstrom