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Timeless Styles

A curated collection of iconic silhouettes that have become hallmarks of the Toscana wardrobe. Crafted in Tuscany from premium Italian leathers, these timeless styles offer exceptional versatility and understated elegance for every occasion.

31style styles
Dark Brown loafer shoe with woven pattern on a wooden surface
NEW

E945 Woven Leather Driving Shoe – Calzoleria Toscana

$398

NEW
Dark Brown
Brick
Merlot
Navy Blue
Moor
Black
Brick genuine crocodile leather loafer on a wooden surface with a light gray background

5124 Dip-Dyed Nile Crocodile Driving Shoe – Calzoleria Toscana

$1,198

Brick
Dark Brown
Black
Navy Blue
White
NEW
Green
Blue leather loafer on a wooden surface with a light gray background

3238-M Ostrich Dress Loafer – Calzoleria Toscana

$738

Navy Blue
Black
NEW
Dark Brown
Black patent leather shoe with red laces on a wooden surface

4849 Patent Leather Cap-Toe Lace-Up – Calzoleria Toscana

$448

Black
Black leather loafer with a gold buckle on a wooden surface

8616-D Cervo Tumbled Leather Horsebit Loafer – Calzoleria Toscana

$398

Black
NEW
Dark Brown
A dusty brown suede penny loafer shoe displayed on a wooden surface
NEW

Quero Velour Suede Wholecut Penny Loafer – Calzoleria Toscana

$428

Dusty Brown
Navy Blue
Black
A single black pebbled leather loafer with a silver-tone horsebit detail, displayed on a wooden surface against a light gray background.
NEW

Stilo Cervo Tumbled Leather Horsebit Loafer - Calzoleria Toscana

$418

Black
Dark Brown
A Burgundy leather penny loafer shoe with a low stacked heel, displayed on a wooden surface
NEW

Zena Penny Loafer - Calzoleria Toscana

$448

Burgundy
Graphite
A chestnut leather double strap monk shoe with brogue detailing and a black heel, displayed on a wooden surface against a light gray background.
NEW

Zerba Blake Rapida Double Monk Strap - Calzoleria Toscana

$508

Chestnut
Black
Black loafer shoe on a wooden surface with a light gray background

Bormio Tassel Loafer – Calzoleria Toscana

$418

Black
NEW
Dark Caramel
Navy blue loafer with a tassel on a wooden surface

Bormio-S Tassel Loafer – Calzoleria Toscana

$418

Blue
Dusty Brown
NEW
Black
Dark Brown leather Chelsea boot on a wooden surface with a light gray background
NEW

Gabor Chelsea Boot – Calzoleria Toscana

$528

Dark Brown
Gray loafer shoe on a wooden surface with a light gray background
NEW

Sommo Velour Suede Venetian Loafer – Calzoleria Toscana

$388

Gray
Brick
Navy Blue
A Dark Brown leather cap-toe oxford dress shoe with a low stacked heel, displayed on a wooden surface against a light gray background.

4849 Cap-Toe Lace-Up – Calzoleria Toscana

$448

NEW
Dark Brown
Straw
NEW
Gray
Black leather dress shoe on a wooden surface with a light gray background
NEW

Midas Scotch Grain Lace-Up – Calzoleria Toscana

$498

Black
Tobacco
Black leather dress shoe on a wooden surface with a light gray background

4633 Cayenne Calfskin Wholecut Balmoral – Calzoleria Toscana

$428

Black
Dark Caramel
Gray
Brick leather loafer on a wooden surface with a light gray background

Izano Dip-Dyed Nile Crocodile Loafer – Calzoleria Toscana

$1,398

Brick
Black
Blue
Moor crocodile-patterned loafer on a wooden surface with a light gray background

4468 Nile Crocodile Venetian Loafer – Calzoleria Toscana

$1,298

Moor
Black
Dark Caramel leather loafer on a wooden surface with a light gray background

7730 Leather Dress Loafer – Calzoleria Toscana

$428

Dark Caramel
Navy Blue
Black
Brown leather oxford dress shoe with a cap toe and subtle perforated detailing, shown in side profile on a wooden surface.

2361 Cayenne Calfskin Cap-Toe Oxford Lace-Up – Calzoleria Toscana

$408

Brown
Blue
Burgundy
Dark Caramel
Black
A burgundy Italian wholecut Oxford shoe with laces on a wooden surface.

9973 Wholecut Oxford Lace-Up – Calzoleria Toscana

$428

Burgundy
Ocean Blue
Graphite
Gray leather dress shoe on a wooden surface with a light gray background

H742 Balmoral Wingtip Lace-Up – Calzoleria Toscana

$408

Gray
Dark Caramel
Blue
Black
Brick pair of leather boots on a wooden surface with a light gray background

9147 Dip-Dyed Wingtip Boot – Calzoleria Toscana

$498

Brick
Moor
Caramel leather shoe with Double buckle on a wooden surface

6582 Double Monk Strap Cap-Toe Shoe – Calzoleria Toscana

$428

Dark Caramel
Blue
Black
Moor

Questions, Answered

About Timeless Styles

  • The Timeless collection brings together our most versatile and signature styles, classic oxfords, loafers, drivers, monk straps, and boots designed to remain relevant season after season. Each pair is handcrafted in Tuscany from premium Italian leathers for lasting style, comfort, and quality.