For years I was deeply invested in the idea that loafers were a “sensible shoe” thing. You know, when faced with poor desk-job shoe options you grab a pair in black and throw yourself miserably into your work trip. I couldn’t have been more wrong. Allow me to correct myself: when worn correctly, the black loafer is one of sexiest, understated things you can put on your feet for a date. I’m sorry to loafers for mocking them for ten years.

The differences between something chic and something trying too hard lie in subtle details you notice on an unconscious level. That slightly chunkier sole to feel modern, not mat schoolteacher. High quality leather that reflects light rather than being flat and matte. Toe shape is important too, too blunt and boxy and it can look clumsy, too sharp and pointy and you just look like it’s 2013.
It all needs a hint of shine, but not too much that it looks lacquered. That’s basically the rubric for everything you own.

So you’ve nailed the shoe itself, how do you wear it? Well this is where the classic black loafer topsoppers of denim-cut slides or things with heels. Once you commit to loafers it’s bare ankle all year round. Rain or shine, if you’re wearing socks with these bad boys you’ve already lost. Pair them with a tailored trouser with a nice sharp crease that hits at the perfect angle to give your legs a break. Or roll up a shirt and slip into a skirt that falls just below the knee, giving you some bare leg to play with before the shoe takes over. Throw it on with a silky button up, half tucked, and you’re looking instantly put together without trying too hard. Pop together in five minutes but screams “I made an effort”, that’s the mood you want to exude on a first or second date.

Speaking of first and second dates, let me tell you about the types of nights the loafer is perfect for. Forget weddings, birthdays, or casual jogs in the park. The shoe perfectly embodies situations with undefined dress codes. It’s not quite a “dressy” dinner date, but something more than just a jeans and basketball shirt casual. Something in between; that nice dinner where you hope you’re going to stay for three drinks but also need to be able to walk home without crying. It’s your shoe for the person who matters but you won’t swear that out loud. It’s comfortable enough that you won’t be preoccupied by constant pressure points, sharp enough that no one will think you didn’t try and dark enough to go with whatever sad desk-job attire you decided to change into five minutes before leaving your apartment.

Top Picks

Franco Sarto Franco Bocca Slip On Loafer (Black Patent) 7.5 W Round Toe
BLACK LOAFERFRANCO SARTOFranco Sarto Franco Bocca Slip On Loafer (Black Patent) 7.5 W Round Toe
$130.00 FRANCO SARTO
LifeStride Malta Loafer Shoes (Black Tumbled Leather) Fabric 7.5
BLACK LOAFERLIFESTRIDELifeStride Malta Loafer Shoes (Black Tumbled Leather) Fabric 7.5
$79.99 $59.99 LIFESTRIDE
Elaina T-Strap Buckle Loafer Black Leather
BLACK LOAFERSAM EDELMANElaina T-Strap Buckle Loafer Black Leather
$139.98 $69.99 SAM EDELMAN
Franco Sarto Franco Bocca Slip On Loafer (Black Patent) 7.5 W Round Toe
FRANCO SARTOFranco Sarto Franco Bocca Slip On Loafer (Black Patent) 7.5 W Round Toe $130.00 FRANCO SARTO
Florsheim Sorrento Moc Toe Penny Loafer Men's Black Slip On 11
SHOEMALL.COMFlorsheim Sorrento Moc Toe Penny Loafer Men's Black Slip On 11 $144.95 SHOEMALL.COM
Clarks Ashland Bubble Loafer Women's Black Slip On 7 N
SHOEMALL.COMClarks Ashland Bubble Loafer Women's Black Slip On 7 N $59.49 SHOEMALL.COM
Franco Sarto Franco Carolynn Tassel Loafer (Black Suede) 9.0 M Slip On Fit, Almond Toe, Slip
FRANCO SARTOFranco Sarto Franco Carolynn Tassel Loafer (Black Suede) 9.0 M Slip On Fit, Almond Toe, Slip $120.00 FRANCO SARTO
Larroudé x Parke Loafer In Black Box Leather - 6.5 / Brown
LARROUDELarroudé x Parke Loafer In Black Box Leather - 6.5 / Brown $325.00 LARROUDE
Florsheim Berkley Flex Penny Loafer Men's Black Slip On 10 B
SHOEMALL.COMFlorsheim Berkley Flex Penny Loafer Men's Black Slip On 10 B $139.95 SHOEMALL.COM
Franco Sarto Franco Maris Bit Loafer (Black Suede) 8.5 M Almond Toe
FRANCO SARTOFranco Sarto Franco Maris Bit Loafer (Black Suede) 8.5 M Almond Toe $140.00 FRANCO SARTO
Square Ribbon Loafer M-IG-180201 Black
W CONCEPT (US)Square Ribbon Loafer M-IG-180201 Black $218.00 W CONCEPT (US)
Salvatore Ferragamo Black Leather Gancini Loafer Pumps
THE LUXURY CLOSETSalvatore Ferragamo Black Leather Gancini Loafer Pumps $313.00 THE LUXURY CLOSET
Johnston & Murphy Ulyssa Studded Loafer Women's Black Slip On 8.5
SHOEMALL.COMJohnston & Murphy Ulyssa Studded Loafer Women's Black Slip On 8.5 $157.95 SHOEMALL.COM
Basic Daily Penny Vegan Leather 2.5cm Heel Loafer
W CONCEPT (US)Basic Daily Penny Vegan Leather 2.5cm Heel Loafer $124.00 W CONCEPT (US)
Nunn Bush Men's Lincoln Loafer Black Slip On 13 W
SHOEMALL.COMNunn Bush Men's Lincoln Loafer Black Slip On 13 W $89.95 SHOEMALL.COM
Nunn Bush Luca Moc Toe Penny Loafer Men's Black Slip On 8 W
SHOEMALL.COMNunn Bush Luca Moc Toe Penny Loafer Men's Black Slip On 8 W $79.95 SHOEMALL.COM
Sorel Joan Now City Loafer Women's Black Slip On 9.5
SHOEMALL.COMSorel Joan Now City Loafer Women's Black Slip On 9.5 $149.99 SHOEMALL.COM
Patent Leather Cushioned Basic Loafer Pumps [Black] (DG1BS25005BLK)
W CONCEPT (US)Patent Leather Cushioned Basic Loafer Pumps [Black] (DG1BS25005BLK) $367.00 W CONCEPT (US)
Franco Sarto Franco Carolynn Tassel Loafer (Camel Brown/black Faux Leather) 7.0 W Slip On Fit, Almond Toe, Slip
FRANCO SARTOFranco Sarto Franco Carolynn Tassel Loafer (Camel Brown/black Faux Leather) 7.0 W Slip On Fit, Almond Toe, Slip $110.00 FRANCO SARTO
Caleocho Genuine Cowhide Leather Penny Loafer (0691) [Black]
W CONCEPT (US)Caleocho Genuine Cowhide Leather Penny Loafer (0691) [Black] $145.00 W CONCEPT (US)
Florsheim Berkley Flex Penny Loafer Men's Black Slip On 8.5
SHOEMALL.COMFlorsheim Berkley Flex Penny Loafer Men's Black Slip On 8.5 $139.95 SHOEMALL.COM
Formel Classic 24 Loafer 1cm (2colors)
W CONCEPT (US)Formel Classic 24 Loafer 1cm (2colors) $103.00 W CONCEPT (US)
Franco Sarto Franco Carolynn Tassel Loafer (Black Patent) 8.5 W Slip On Fit, Almond Toe, Slip
FRANCO SARTOFranco Sarto Franco Carolynn Tassel Loafer (Black Patent) 8.5 W Slip On Fit, Almond Toe, Slip $110.00 FRANCO SARTO
KENNETH COLE Loafer Shoes Black Leather Mens UK 6.5
CERQULARKENNETH COLE Loafer Shoes Black Leather Mens UK 6.5 $94.89 CERQULAR
1805 Savage Penny Loafer Matt Loafers [Black]
W CONCEPT (US)1805 Savage Penny Loafer Matt Loafers [Black] $106.00 W CONCEPT (US)
Simone Rocha Tracker Loafer Fringed Leather Sneakers - Black - 36 (IT36 / UK3)
HARVEY NICHOLS USSimone Rocha Tracker Loafer Fringed Leather Sneakers - Black - 36 (IT36 / UK3) $895.17 HARVEY NICHOLS US
MARC FISHER Loafer Shoes Black Leather Womens UK
CERQULARMARC FISHER Loafer Shoes Black Leather Womens UK $31.19 CERQULAR
BAZLLY SUISSE Womens Tassel Loafer Leather Shoes Black UK 7 Classic Formal
CERQULARBAZLLY SUISSE Womens Tassel Loafer Leather Shoes Black UK 7 Classic Formal $37.69 CERQULAR
Dr. Scholl's Women's Hello Loafer Shoes Black Shiny Faux Leather DRSCH 10.0
DR. SCHOLL'S SHOESDr. Scholl's Women's Hello Loafer Shoes Black Shiny Faux Leather DRSCH 10.0 $70.00 DR. SCHOLL'S SHOES
Braided Buckle Twisted Leather Loafer [Black Beige] (DG1DS25016BWX)
W CONCEPT (US)Braided Buckle Twisted Leather Loafer [Black Beige] (DG1DS25016BWX) $394.00 W CONCEPT (US)
T006 Jane Loafer Black (2cm)
W CONCEPT (US)T006 Jane Loafer Black (2cm) $189.00 W CONCEPT (US)
−84%Women Gosh-03 Slip On Loafer BLACK Flats 6.5 BLACK
SHIEKHWomen Gosh-03 Slip On Loafer BLACK Flats 6.5 BLACK$24.94 $3.99 SHIEKH
−33%Dr. Scholl's Women's Veda Loafer Shoes Black Faux Leather DRSCH 7.5
DR. SCHOLL'S SHOESDr. Scholl's Women's Veda Loafer Shoes Black Faux Leather DRSCH 7.5$59.69 $39.99 DR. SCHOLL'S SHOES
−47%Dr. Scholl's Women's Jetset Loafer Shoes Black Black Leather DRSCH 8.0
DR. SCHOLL'S SHOESDr. Scholl's Women's Jetset Loafer Shoes Black Black Leather DRSCH 8.0$94.32 $49.99 DR. SCHOLL'S SHOES
−55%Soul Achieve Wedge Shoes, Black Synthetic, 12.0M Loafer Style, Slip-On Fit, Round Toe
NATURALIZERSoul Achieve Wedge Shoes, Black Synthetic, 12.0M Loafer Style, Slip-On Fit, Round Toe$111.09 $49.99 NATURALIZER
−44%LifeStride London Loafer Shoes (Black Synthetic) Leather 9.5
LIFESTRIDELifeStride London Loafer Shoes (Black Synthetic) Leather 9.5$89.27 $49.99 LIFESTRIDE
−39%LifeStride London 2 Loafer Shoes (Black Patent Faux Leather) 7.0
LIFESTRIDELifeStride London 2 Loafer Shoes (Black Patent Faux Leather) 7.0$90.15 $54.99 LIFESTRIDE
−39%LifeStride London 2 Loafer Shoes (Black Faux Leather) 7.5 W
LIFESTRIDELifeStride London 2 Loafer Shoes (Black Faux Leather) 7.5 W$90.15 $54.99 LIFESTRIDE
−31%Dr. Scholl's Women's Webster Loafer Shoes Black Snake DRSCH Leather 9.0
DR. SCHOLL'S SHOESDr. Scholl's Women's Webster Loafer Shoes Black Snake DRSCH Leather 9.0$79.70 $54.99 DR. SCHOLL'S SHOES
−50%Naturalizer Elin Loafer Shoes, Black/Leopard Faux Leather Microfiber, 9.0W Slip-On Fit, Almond Toe
NATURALIZERNaturalizer Elin Loafer Shoes, Black/Leopard Faux Leather Microfiber, 9.0W Slip-On Fit, Almond Toe$119.98 $59.99 NATURALIZER
−25%LifeStride Malta Loafer Shoes (Black Tumbled Leather) Fabric 7.5
LIFESTRIDELifeStride Malta Loafer Shoes (Black Tumbled Leather) Fabric 7.5$79.99 $59.99 LIFESTRIDE
−50%Naturalizer Elin Loafer Shoes, Black Perforated Faux Leather Microfiber, 8.0W Slip-On Fit, Almond Toe
NATURALIZERNaturalizer Elin Loafer Shoes, Black Perforated Faux Leather Microfiber, 8.0W Slip-On Fit, Almond Toe$119.98 $59.99 NATURALIZER
−25%LifeStride Zee Loafer Shoes (Black Patent) Fabric 11.0 W
LIFESTRIDELifeStride Zee Loafer Shoes (Black Patent) Fabric 11.0 W$79.99 $59.99 LIFESTRIDE
−25%LifeStride Frankie Slip On Loafer Shoes (Black Pebble Faux Leather) Fabric 11.0 W
LIFESTRIDELifeStride Frankie Slip On Loafer Shoes (Black Pebble Faux Leather) Fabric 11.0 W$85.32 $63.99 LIFESTRIDE
−24%LifeStride London 3 Loafer Shoes (Black Smooth Leather) 8.0
LIFESTRIDELifeStride London 3 Loafer Shoes (Black Smooth Leather) 8.0$89.46 $67.99 LIFESTRIDE
−24%Bzees For LifeStride Kandi Moc Loafer Shoes (Black Knit Fabric) 11.0
LIFESTRIDEBzees For LifeStride Kandi Moc Loafer Shoes (Black Knit Fabric) 11.0$89.46 $67.99 LIFESTRIDE
−50%Elaina T-Strap Buckle Loafer Black Leather
SAM EDELMANElaina T-Strap Buckle Loafer Black Leather$139.98 $69.99 SAM EDELMAN
−48%Franco Sarto Franco Sully Slingback Loafer (Black Leather) 8.0 M Round Toe, Buckle Closure
FRANCO SARTOFranco Sarto Franco Sully Slingback Loafer (Black Leather) 8.0 M Round Toe, Buckle Closure$144.19 $74.98 FRANCO SARTO
−23%Naturalizer Dahlia Loafer Shoes, Black Faux Leather Fabric, 5.5M Slip-On Fit, Round Toe
NATURALIZERNaturalizer Dahlia Loafer Shoes, Black Faux Leather Fabric, 5.5M Slip-On Fit, Round Toe$110.38 $84.99 NATURALIZER
−33%Franco Sarto Franco Mirabelle Loafer (Black Patent Faux Leather) 8.5 M Almond Toe
FRANCO SARTOFranco Sarto Franco Mirabelle Loafer (Black Patent Faux Leather) 8.5 M Almond Toe$134.30 $89.98 FRANCO SARTO
−17%Naturalizer Cabaret Loafer Shoes, Black Synthetic, 8.0M Slip-On Fit, Round Toe, Block Heels
NATURALIZERNaturalizer Cabaret Loafer Shoes, Black Synthetic, 8.0M Slip-On Fit, Round Toe, Block Heels$120.47 $99.99 NATURALIZER
−7%Naturalizer Bloom Loafer Shoes, Black Leather Suede, 6.5M Slip-On, Round Toe, Block Heels
NATURALIZERNaturalizer Bloom Loafer Shoes, Black Leather Suede, 6.5M Slip-On, Round Toe, Block Heels$139.77 $129.99 NATURALIZER
−20%Kate Spade Leandra Heeled Loafer, Black - 9.5
KATE SPADE OUTLETKate Spade Leandra Heeled Loafer, Black - 9.5$247.50 $198.00 KATE SPADE OUTLET

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