Streetwear Oversized Shorts That Look Like They Cost More

Top Picks

JAMIE’S PICK SELDOM SEEN STYLESSnow Camo Cargo Shorts Teddy Bear Pendant Cartoon Patch Multi Pocket High Waist Casual Streetwear Baggy Shorts

$65.00 SELDOM SEEN STYLES

ANDRE’S PICK SELDOM SEEN STYLESStar Print Number 34 Embroidery Wide-Leg Sweat Shorts

$58.00 SELDOM SEEN STYLES

LIAM’S PICK SELDOM SEEN STYLESDrawstring Jogger Shorts Elastic Waist Casual Loose Fit Summer Lightweight Lounge Shorts

$45.00 SELDOM SEEN STYLES

RYAN’S PICK SELDOM SEEN STYLES©SAINT M×××××× "I Heart Saint" Fleece Shorts 'White/Off-White'

$55.00 SELDOM SEEN STYLES

DEREK’S PICK AFEWVIBE LTDDenim Tears The Cotton Wreath Shorts Royal Blue

$200.00 AFEWVIBE LTD

How we pick

Quick word on how this list was made. Jamie, Andre, Liam, Ryan and Derek picked their favourites from the streetwear oversized shorts we found across loads of shops. No sponsored spots, no brand deals, just what they'd buy with their own money. We keep a mix of prices so there's something whether you're treating yourself or being sensible this month, and we limit how many come from one retailer. Stock and prices update regularly from each shop, so if something's gone, it's sold out rather than hidden.

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Up to $10015 pieces

Streetwear Oversized Shorts That Look Like They Cost More

Drawstring Jogger Shorts Elastic Waist Casual Loose Fit Summer Lightweight Lounge Shorts

Knit Drawstring Shorts

Letter Print Wide Leg Denim Shorts High Waist Washed Streetwear Summer Casual Shorts

Vintage Washed Multi-Pocket Denim Cargo Shorts

That's A Awful Lot Of Cough Syrup "Texas Edition" White Fleece Shorts

Hellstar Studded Flame Face Shorts 'Pink'

Colorful Button Embellished Wide Leg Denim Shorts Arc Seam Detail High Waist Casual Streetwear Baggy Jean Shorts

DARKAGE Vintage Washed Sunburst Pleated Denim Shorts

Saint Michael SS26 Metal Multi Font Sweat Shorts Charcoal

Snow Camo Cargo Shorts Teddy Bear Pendant Cartoon Patch Multi Pocket High Waist Casual Streetwear Baggy Shorts

©SAINT M×××××× "I Heart Saint" Fleece Shorts 'White/Off-White'

Loose Fit Cargo Shorts Elastic Waist Multi Pocket Drawstring Casual Summer Streetwear Unisex Wide Leg Shorts

Star Print Number 34 Embroidery Wide-Leg Sweat Shorts

Hellstar Sports Shorts

©SAINT M×××××× "SAINT" Applique Fleece Shorts 'Charcoal/Orange'

Denim Tears The Cotton Wreath Shorts Pink

Denim Tears The Cotton Wreath Shorts Royal Blue

Denim Tears The Cotton Wreath Shorts Brown

Denim Tears The Cotton Wreath Shorts Black

HELLSTAR NYLON SHORTS BLACK

Hellstar Flame Shorts Pink

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