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. 

115 items
Dungaree dress with headband - pink/bow aop
OFFER

Dungaree dress with headband - pink/bow aop

Pop Candy

R167

R279

-40%

Mini floral balloon sleeve dress - multi
SALE

Mini floral balloon sleeve dress - multi

Trendyol

R320

R799

-60%

Puff sleeve dress - black & white
SALE

Puff sleeve dress - black & white

Pop Candy

R150

R299

-50%

Frill-trimmed strappy dress - light beige floral

Frill-trimmed strappy dress - light beige floral

H&M

R379

Dropped waist dress with shirred bodice - leopard print
SALE

Dropped waist dress with shirred bodice - leopard print

Pop Candy

R160

R399

-60%

Tulle-skirt sweatshirt dress - pink,multi

Tulle-skirt sweatshirt dress - pink,multi

H&M

R329

Check tunic dress with ribbed long sleeve top - burgundy/cream
OFFER

Check tunic dress with ribbed long sleeve top - burgundy/cream

Pop Candy

R349

R499

-30%

Tiered dress with spaghetti straps - pink & green floral
SALE

Tiered dress with spaghetti straps - pink & green floral

Pop Candy

R132

R329

-60%

Bow embellished sweatshirt with tulle skirt - grey/black

Bow embellished sweatshirt with tulle skirt - grey/black

Pop Candy

R349

Bridget midi dress - roses floral
SALE

Bridget midi dress - roses floral

Cotton On

R500

R999

-50%

Peplum blouse - light yellow spotted
SALE

Peplum blouse - light yellow spotted

H&M

R112

R249

-55%

Fleece sweat top & leggings - white/bow aop/pink
OFFER

Fleece sweat top & leggings - white/bow aop/pink

Pop Candy

R219

R399

-45%

Spaghetti strap top & skirt set - multi
OFFER

Spaghetti strap top & skirt set - multi

Pop Candy

R159

R399

-60%

Plissé chiffon dress - pink & multi-coloured

Plissé chiffon dress - pink & multi-coloured

H&M

R349

Gypsy skirt dress with double bow detail - ivory/floral aop
SALE

Gypsy skirt dress with double bow detail - ivory/floral aop

Pop Candy

R180

R399

-55%

Maxi A line Polka Dot Knit Dress - Black & White
SALE

Maxi A line Polka Dot Knit Dress - Black & White

Trendyol

R450

R999

-55%

Tweed collarless jacket with pleated skirt - black/white
OFFER

Tweed collarless jacket with pleated skirt - black/white

Pop Candy

R489

R699

-30%

Ladies V-Neck Short Sleeve Mini Printed Dress - Black & Red Spot
SALE

Ladies V-Neck Short Sleeve Mini Printed Dress - Black & Red Spot

Brave Soul

R210

R599

-65%

Shirred bodice dress - beige
OFFER

Shirred bodice dress - beige

Pop Candy

R170

R379

-55%

Tulle-skirt sweatshirt dress - light grey marl/rainbow

Tulle-skirt sweatshirt dress - light grey marl/rainbow

H&M

R329

Embroidered tulle skirt - white floral

Embroidered tulle skirt - white floral

H&M

R529

Butterfly-sleeved dress - cream/floral

Butterfly-sleeved dress - cream/floral

H&M

R629

Printed S/S Mini Floral Dress With Small Button Detail - Multi White
OFFER

Printed S/S Mini Floral Dress With Small Button Detail - Multi White

Stella Morgan

R839

R1199

-30%

4 piece outfit set - cream/burgundy/check
OFFER

4 piece outfit set - cream/burgundy/check

Pop Candy

R559

R799

-30%

Frill-trimmed strappy dress - green/floral

Frill-trimmed strappy dress - green/floral

H&M

R329

Sleeveless cropped tee & maxi skirt with flare set - light pink floral
SALE

Sleeveless cropped tee & maxi skirt with flare set - light pink floral

Pop Candy

R180

R449

-60%

Sheer strappy dress - beige/leopard print
SALE

Sheer strappy dress - beige/leopard print

H&M

R214

R329

-35%

2-Piece dress and top set - light beige/denim black

2-Piece dress and top set - light beige/denim black

H&M

R499

Ladies Floral Puff Sleeve Mini DressWith Sweatheart Neckline - Multi Floral
SALE

Ladies Floral Puff Sleeve Mini DressWith Sweatheart Neckline - Multi Floral

Brave Soul

R210

R599

-65%

Ditsy floral oversized ruffle collar dress - off white
OFFER

Ditsy floral oversized ruffle collar dress - off white

Pop Candy

R336

R449

-25%

Ladies Playsuit With Tie Straps Floral Print - multi
SALE

Ladies Playsuit With Tie Straps Floral Print - multi

Brave Soul

R240

R599

-60%

Leopard rope satin nightdress - pink-multicolor
SALE

Leopard rope satin nightdress - pink-multicolor

Trendyol

R270

R599

-55%

Sweatshirt with pleated skirt - navy/white
OFFER

Sweatshirt with pleated skirt - navy/white

Pop Candy

R269

R449

-40%

Tiered mini skirt - dusty pink patterned
SALE
5 options

Tiered mini skirt - dusty pink patterned

H&M

R131

R329

-60%

Plush night gown - purple gradient/unicorn aop
OFFER
3 options

Plush night gown - purple gradient/unicorn aop

Pop Candy

R284

R379

-25%

Maxi Aline Woven Dress - Multi Floral
OFFER

Maxi Aline Woven Dress - Multi Floral

Trendyol

R359

R899

-60%

Houndstooth printed wool-blend jacket and skirt - black
OFFER

Houndstooth printed wool-blend jacket and skirt - black

Pop Candy

R359

R449

-20%

Sweater & wide leg sweatpant set - white/pink
OFFER

Sweater & wide leg sweatpant set - white/pink

Pop Candy

R249

R499

-50%

L/S Mandarin Collar Button Through Maxi Dress With Binding Throughout - Multi Pink
OFFER

L/S Mandarin Collar Button Through Maxi Dress With Binding Throughout - Multi Pink

Stella Morgan

R1349

R1799

-25%

Plus Chiffon Printed Ruffle Cold Shoulder Slip Dress - Leopard
SALE

Plus Chiffon Printed Ruffle Cold Shoulder Slip Dress - Leopard

boohoo

R450

R999

-55%

Rugby jersey-style sweatshirt - white/black stripes
OFFER
2 options

Rugby jersey-style sweatshirt - white/black stripes

Pop Candy

R244

R349

-30%

Printed sundress - multi
SALE

Printed sundress - multi

MILLA

R490

R1399

-65%

Tiered mini skirt - light blue patterned
SALE
5 options

Tiered mini skirt - light blue patterned

H&M

R181

R329

-45%

Gingham peplum camisole & pants - maroon/grey
OFFER

Gingham peplum camisole & pants - maroon/grey

Pop Candy

R339

R399

-15%

Lace-detail dress - white,multi

Lace-detail dress - white,multi

H&M

R399

Shirred bodice dress - leopard print
SALE

Shirred bodice dress - leopard print

Pop Candy

R150

R299

-50%

Tulle skirt - light beige cherries
SALE

Tulle skirt - light beige cherries

H&M

R153

R279

-45%

Polka dot onion quilted collarless jacket - barley white/black
OFFER

Polka dot onion quilted collarless jacket - barley white/black

Pop Candy

R489

R699

-30%

Bead-detail cape dress - cream

Bead-detail cape dress - cream

H&M

R1199

Airy drawstring shorts - beige paisley-patterned
SALE
2 options

Airy drawstring shorts - beige paisley-patterned

H&M

R259

R399

-35%

Tie-detail satin dress - red-orange
SALE

Tie-detail satin dress - red-orange

H&M

R172

R429

-60%

A-line dress - beige leopard print

A-line dress - beige leopard print

H&M

R379

Belted shirt dress - cream striped
2 options

Belted shirt dress - cream striped

H&M

R549

Barbie Fashion Backpack - black & pink
OFFER

Barbie Fashion Backpack - black & pink

Character Group

R195

R279

-30%

Wmn Layla Printed Skirt - Black & Grey
OFFER

Wmn Layla Printed Skirt - Black & Grey

POLO

R1494

R2299

-35%

Fleece dressing gown - dark red hearts

Fleece dressing gown - dark red hearts

H&M

R329

Stripe jersey with buttons - white/navy
OFFER

Stripe jersey with buttons - white/navy

Pop Candy

R191

R349

-45%

Lace hem golfer dress with embroidered bow - black/cream
SALE

Lace hem golfer dress with embroidered bow - black/cream

Pop Candy

R225

R499

-55%

Snake Pattern Lined Chiffon Dress - Green
OFFER

Snake Pattern Lined Chiffon Dress - Green

Trendyol

R1124

R1499

-25%

Leopard floral mix chiffon corset maxi dress - multi
SALE

Leopard floral mix chiffon corset maxi dress - multi

boohoo

R210

R599

-65%

Crochet-look skirt - black & light beige
SALE

Crochet-look skirt - black & light beige

H&M

R494

R1099

-55%

Pleated collar dress - milk punch/floral aop
OFFER

Pleated collar dress - milk punch/floral aop

Pop Candy

R153

R279

-45%

Gown & pj set - cream/bear aop
OFFER

Gown & pj set - cream/bear aop

Pop Candy

R324

R499

-35%

Striped high-neck cardigan - red/white
SALE

Striped high-neck cardigan - red/white

Pop Candy

R175

R349

-50%

Mini Woven A line Open Back Dress - Multi
SALE

Mini Woven A line Open Back Dress - Multi

Trendyol

R405

R899

-55%

Smocked blouse - black patterned

Smocked blouse - black patterned

H&M

R399

Paris Saint-Germain 2026/27 Stadium Home Replica Jersey

Paris Saint-Germain 2026/27 Stadium Home Replica Jersey

Nike

R1299

Patterned Knitted Pajama Set - Multicolored Cherry
SALE

Patterned Knitted Pajama Set - Multicolored Cherry

Trendyol

R280

R799

-65%

Printed satin shirt - blue paisley pattern

Printed satin shirt - blue paisley pattern

H&M

R379

Tartan check boucle jacket with faux fur lining - pink
OFFER

Tartan check boucle jacket with faux fur lining - pink

Pop Candy

R639

R799

-20%

Belted Midi Lined Woven Dress - Multi-Colored
OFFER

Belted Midi Lined Woven Dress - Multi-Colored

Trendyol

R909

R1299

-30%

Ls Ilenia Pleat Long Dress - Safari Bloom Print
OFFER

Ls Ilenia Pleat Long Dress - Safari Bloom Print

GUESS

R1959

R2799

-30%

sissy boy dresses

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