SISSY BOY DRESSES

mini, midi + maxi

For the bold woman not afraid to make a statement, Sissy Boy dresses will make sure you're the centre of attention. 

54 items
Wide Awake Maxi Dress - Black

Wide Awake Maxi Dress - Black

SISSY BOY

R2499

Sweet Escape Maxi Dress With A Dropped Waist And Ruching - Black
SALE

Sweet Escape Maxi Dress With A Dropped Waist And Ruching - Black

SISSY BOY

R675

R1499

-55%

Dazzle Me Maxi Dress: Basic Glam Maxi Dress With Cutline - Neutral
SALE

Dazzle Me Maxi Dress: Basic Glam Maxi Dress With Cutline - Neutral

SISSY BOY

R585

R1299

-55%

Asymmetric Maxi Dress With Ruching - Black
SALE

Asymmetric Maxi Dress With Ruching - Black

SISSY BOY

R585

R1299

-55%

Turn Back Time: Maxi Dress - Burgundy
SALE

Turn Back Time: Maxi Dress - Burgundy

SISSY BOY

R600

R1199

-50%

One Of A Kind Midi Dress With An Underbust Cutline And Gauging - Off White
OFFER

One Of A Kind Midi Dress With An Underbust Cutline And Gauging - Off White

SISSY BOY

R649

R1299

-50%

Sweet Escape Maxi Dress With A Dropped Waist And Ruching - Burgundy
OFFER

Sweet Escape Maxi Dress With A Dropped Waist And Ruching - Burgundy

SISSY BOY

R674

R1499

-55%

Switch It Up: Mini Dress With Gauging In The Waist And A Sweet Heart Neckline - Black
OFFER

Switch It Up: Mini Dress With Gauging In The Waist And A Sweet Heart Neckline - Black

SISSY BOY

R494

R899

-45%

Bold Statement Maxi Dress With A Straight Neckline And Curved Slit With Diamante Trim - Black
SALE

Bold Statement Maxi Dress With A Straight Neckline And Curved Slit With Diamante Trim - Black

SISSY BOY

R630

R1399

-55%

Bold Statement Maxi Dress With A Straight Neckline And Curved Slit With Diamante Trim - Burgundy
SALE

Bold Statement Maxi Dress With A Straight Neckline And Curved Slit With Diamante Trim - Burgundy

SISSY BOY

R630

R1399

-55%

Belive In Me: Mini Dress With Bow Straps - Ruby Red
SALE

Belive In Me: Mini Dress With Bow Straps - Ruby Red

SISSY BOY

R500

R999

-50%

Mini Denim Dress With Slit And Diamante Bows - Desize

Mini Denim Dress With Slit And Diamante Bows - Desize

SISSY BOY

R1199

Stay Golden: High Neck Mini Dress With Low Back - Blue / Gold
OFFER

Stay Golden: High Neck Mini Dress With Low Back - Blue / Gold

SISSY BOY

R599

R999

-40%

Wish For This Maxi Dress - Mocha Mousse
OFFER

Wish For This Maxi Dress - Mocha Mousse

SISSY BOY

R1199

R1499

-20%

Take Your Time Mini Dress With A Straight Neckline, Godets And Halterneck Straps - Black
SALE

Take Your Time Mini Dress With A Straight Neckline, Godets And Halterneck Straps - Black

SISSY BOY

R450

R999

-55%

Scoop Neck Maxi Dress With Slit Details - Silver Multi
OFFER

Scoop Neck Maxi Dress With Slit Details - Silver Multi

SISSY BOY

R719

R1599

-55%

Mini Dress With An Underbust Cutline And Open Back Details - Black
OFFER

Mini Dress With An Underbust Cutline And Open Back Details - Black

SISSY BOY

R1199

R1499

-20%

Cherry Bomb: Maxi Dress With Lace Trim Details - Black
SALE

Cherry Bomb: Maxi Dress With Lace Trim Details - Black

SISSY BOY

R675

R1499

-55%

Give My All:Basic Glam Maxi Dress - Pink / Blue
OFFER

Give My All:Basic Glam Maxi Dress - Pink / Blue

SISSY BOY

R749

R1499

-50%

Champagne Problems Dress- Bottle Green
OFFER

Champagne Problems Dress- Bottle Green

SISSY BOY

R1039

R1299

-20%

Give My All: Basic Glam Maxi Dress - Black
SALE

Give My All: Basic Glam Maxi Dress - Black

SISSY BOY

R805

R2299

-65%

Not My Problem Mini Dress - Burgundy
OFFER

Not My Problem Mini Dress - Burgundy

SISSY BOY

R599

R1199

-50%

Dream On: Mini Dress With A Dropped Waist And Gauging - Black
SALE

Dream On: Mini Dress With A Dropped Waist And Gauging - Black

SISSY BOY

R450

R999

-55%

Take Your Timemini Dress With A Straight Neckline, Godets And Halterneck Straps - Off White
SALE

Take Your Timemini Dress With A Straight Neckline, Godets And Halterneck Straps - Off White

SISSY BOY

R450

R999

-55%

Date Night Mini Dress With Ruching And An Underbust Cutline - Black
SALE

Date Night Mini Dress With Ruching And An Underbust Cutline - Black

SISSY BOY

R315

R699

-55%

Mini Dress With A Halter Neckline And Ruching - Black
OFFER

Mini Dress With A Halter Neckline And Ruching - Black

SISSY BOY

R649

R1299

-50%

Strappy Maxi Dress With A Straight Neckline And Ruffle Details - Pale Blue
SALE

Strappy Maxi Dress With A Straight Neckline And Ruffle Details - Pale Blue

SISSY BOY

R765

R1699

-55%

Give My All:Basic Glam Maxi Dress - Black
SALE

Give My All:Basic Glam Maxi Dress - Black

SISSY BOY

R585

R1299

-55%

Maxi Dress With A V-Neckline - Multi
SALE

Maxi Dress With A V-Neckline - Multi

SISSY BOY

R1125

R2499

-55%

Strappy Maxi Dress With Slit And Bling Trim - Black

Strappy Maxi Dress With Slit And Bling Trim - Black

SISSY BOY

R1399

One To Watch: Basic Glam Maxi Dress With Shaped Neckline - Black/Holographic
SALE

One To Watch: Basic Glam Maxi Dress With Shaped Neckline - Black/Holographic

SISSY BOY

R800

R1999

-60%

Living Lux: Blouson Mini Dress With High Neck And Dropped Waist - Off White/Pink Multi
SALE

Living Lux: Blouson Mini Dress With High Neck And Dropped Waist - Off White/Pink Multi

SISSY BOY

R540

R1199

-55%

Roses Are Red: Maxi Dress With Ruching Over The Bust - Off White
OFFER

Roses Are Red: Maxi Dress With Ruching Over The Bust - Off White

SISSY BOY

R699

R1399

-50%

Tulle Mini Dress With Cups, Gauging And Small Bows - Red
SALE

Tulle Mini Dress With Cups, Gauging And Small Bows - Red

SISSY BOY

R855

R1899

-55%

Aurelia Tiered Maxi Dress - Off White
OFFER

Aurelia Tiered Maxi Dress - Off White

SISSY BOY

R1039

R1599

-35%

Mini Dress With Asymmetric Ruffle Skirt And Crochet Trim - Black
SALE

Mini Dress With Asymmetric Ruffle Skirt And Crochet Trim - Black

SISSY BOY

R560

R1399

-60%

Sea La Vie Boobtube Mini Dress With Small Cutout And Trim Detail - Black
SALE

Sea La Vie Boobtube Mini Dress With Small Cutout And Trim Detail - Black

SISSY BOY

R540

R1199

-55%

Date Night Mini Dress With Ruching And An Underbust Cutline - Pink
SALE

Date Night Mini Dress With Ruching And An Underbust Cutline - Pink

SISSY BOY

R350

R699

-50%

Borrowed Hearts Maxi Dress With Mermaid Styled Skirt - Black
OFFER

Borrowed Hearts Maxi Dress With Mermaid Styled Skirt - Black

SISSY BOY

R844

R1299

-35%

Talk About Us Mini Dress Bandage Mini Dress With Cups - Black
OFFER

Talk About Us Mini Dress Bandage Mini Dress With Cups - Black

SISSY BOY

R1689

R2599

-35%

Lucky Ones: A-Line Mini Dress With A V-Neck - Neutral
OFFER

Lucky Ones: A-Line Mini Dress With A V-Neck - Neutral

SISSY BOY

R749

R1499

-50%

Always Present Mini Dress With An Underbust Cutline And Ruching Detail - Black/Red Print
SALE

Always Present Mini Dress With An Underbust Cutline And Ruching Detail - Black/Red Print

SISSY BOY

R360

R799

-55%

Bright Lights: Knit Maxi Dress With Rhinestones Detail - Black
OFFER

Bright Lights: Knit Maxi Dress With Rhinestones Detail - Black

SISSY BOY

R999

R1999

-50%

So Loved: Mini Dress - Black
SALE

So Loved: Mini Dress - Black

SISSY BOY

R600

R1199

-50%

Baby Doll: Mini Dress With Ruching And A Shaped Hem - Green
SALE

Baby Doll: Mini Dress With Ruching And A Shaped Hem - Green

SISSY BOY

R585

R1299

-55%

High neck mini dress with low back - gold

High neck mini dress with low back - gold

SISSY BOY

R1599

Full Of Love Tulle Mini Dress With Cups, Gauging And Small Bows - Cerise
SALE

Full Of Love Tulle Mini Dress With Cups, Gauging And Small Bows - Cerise

SISSY BOY

R855

R1899

-55%

Tulle Mini Dress With Cups, Gauging And Small Bows - Black
SALE

Tulle Mini Dress With Cups, Gauging And Small Bows - Black

SISSY BOY

R855

R1899

-55%

Whisked Away Mini Dress Bandage Mini Dress - Red
OFFER

Whisked Away Mini Dress Bandage Mini Dress - Red

SISSY BOY

R1494

R2299

-35%

Sparks Fly: Mini Dress - White
SALE

Sparks Fly: Mini Dress - White

SISSY BOY

R714

R1299

-45%

Crochet And Denim Playsuit - Light Vintage
SALE

Crochet And Denim Playsuit - Light Vintage

SISSY BOY

R700

R1399

-50%

Oceane: Strappy Lurex Flared Dress - Black / Silver Lurex
SALE

Oceane: Strappy Lurex Flared Dress - Black / Silver Lurex

SISSY BOY

R810

R1799

-55%

Boobtube Mini Dress With Small Cutout And Trim Detail - Red
SALE

Boobtube Mini Dress With Small Cutout And Trim Detail - Red

SISSY BOY

R600

R1199

-50%

TRUTH BE TOLD: Maxi Dress With A Corsetted Bodice And Pleated Skirt - Bottle Green
OFFER

TRUTH BE TOLD: Maxi Dress With A Corsetted Bodice And Pleated Skirt - Bottle Green

SISSY BOY

R599

R1199

-50%

sissy boy dresses

Founded in 1986 by Ronald Sassoon, one of South Africa’s leading denim pioneers, Sissy Boy has become a famous name in the South African retail market. While they are best known for their jeans, Sissy Boy has expanded to help women find their perfect fashion fit across various clothing categories. Sissy Boy dresses of classic yet trendy, perfect for the woman with edge. Sissy Boy is not afraid to go bold, with vibrant printed dresses that command attention. From mini dresses and mid-length fits to formal gowns, find whatever style you need right now with Sissy Boy.

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