You can do this over multiple playthroughs, just make sure to save after wearing clothing, if you die before you do they don't count. Thanks to DisguisedMike for confirming.
You do NOT need the unlockable clothes that can be worn from the safe room locker for this achievement. Thanks to TheBlackDragonX for confirming this. This includes the Knight boots from the pawn shop. Thanks to NuffinButSteele for confirming this.
One item of clothing in Kokonutz Sports Town is only accessible for a short time from 6am on day 3 (around case 4-1 in the story). There's more information on it at the end of the guide, but you should definitely keep it in mind when you're going for the achievement.
Royal Flush 1st floor;
In The Closet: (2) Hip Hop Outfit, Skater Outfit.
Casual gals: (2) Ladies Hat, Knotted Top Cutoffs.
Stylin' Toddlers: (2) One-Piece Pajama, Kids Super Hero Boots.
Astonishing Illusions: (1) Novelty Glasses.
Three Club Monte: (1) Polo Shirt Blue Jeans.
Universe of Optics: (3) Aviator Glasses, Sport Glasses, Yellow Tinted Glasses.
Hat Racks: (1) Tourist Boat Hat.
SporTrance: (2) Football Uniform, Football Helmet.
The Shoehorn: (1) Black Canvas Sneakers.
Wave of Style: (2) Blue Hair, Full Beard Moustache.
Ye Olde Toybox: (1) Funny Lizard Mask.
Roy's Mart: (1) Hygiene Mask.
Modern Businessman: (2) Collegiate Ensemble (NOT listed on map at all), Business Casual.
Royal Flush 2nd Floor;
Children's Castle: (2) Funny Goblin Mask, Kids Super Hero Eye Mask.
Earmark Leather: (6) Black Cowboy Outfit, White Cowboy Outfit, White Cowboy Boots, Black Cowboy Boots, White Cowboy Hat, Black Cowboy Hat.
Kathy's Space: (1) Tube Top Mini Skirt.
Estelle's Fine-Lady Cosmetics: (1) Grey Hair.
Albert's Apparel: (1) Plaid Suit.
Slot Ranch Casino;
Back Stage Area: (1) Show Girl Head Piece.
Kiosk Surrounded by Trees (see map): (1) Moosehead.
Yucatan Casino (see map);
Room where Lenny is rescued: (1) Dealer Outfit.
Beside Safe where drill is located in case 3-1: (1) Dealer Visor. (For alternate location see Americana).
Palisades Mall 1st Floor;
Shank's: (2) Shaved Head, Mohawk Hair.
Bagged!: (1) Black Dress Shoes.
The Venus Touch: (1) Grey Hair.
KokoNutz Sports Town: (4) Tennis Uniform (NOT listed on map at all) Basketball Uniform, White Tennis Shoes, Tennis Head Band,
KokoNutz Locked Room: (1) Mid Length Tshirt Jeans (See * at end).
For Your Leisure: (3) Business Casual, Polo Shirt Blue Jeans, Sandals.
Trendy Cindy: (1) Knotted Top Cutoffs.
Finders Peepers: (2) Rocker Glasses, Black Rimmed Glasses.
FairMoans: (2) Pink Hair, Blue Hair.
Ultimate Playhouse: (2) Funny Servbot Mask, Kids Super Hero Costume.
Beach Body Swim House: (3) Sport Glasses, Surf Wetsuit, Banana Hammock.
Wallington's: (2) Highbrow Ensemble, Tuxedo.
Palisades Mall 2nd Floor;
Kids' Choice Clothing: (2) Toddler Outfit, Funny Zombie Mask.
under the Sea Travels: (1) Hula Dress.
Space: (6) Yellow Track Suit, Yellow Sneakers, Loud Summer Special, Boardwalk Appeal, Wild Frontier Hat, Tourist Boat Hat.
Brand New U: (3) Summer Dress, Tube Top Mini Skirt, White Low Heels.
Que's Hats: (4) Knit Cap, Russian Hat, Fedora, Ladies Hat.
Kicks For Her: (2) Go-go Boots, Bunny Slippers.
High-Noon Shooting Range: (4) Swat Helmet, Swat Outfit, Black Military Boots, Army Jacket Pants.
KokoNutz Sports Town: (5) Basketball High Tops, Baseball Cap Sport, Baseball Uniform, Sporty Track Suit, Cleats.
South Plaza (see map);
Outside Maintenance Room after save Point: (1)Blue Grey Work Overalls.
Large Shop Near Arena: (1) Underwear.
Hostile Zone (map points to wrong shop): (2) Baseball Cap TIR, TIR Outfit.
The American Historium; (4) White Leisure Suit, Fortune City Red Shirt, American Showman Jumpsuit, American Showman Helmet.
Shots and Awe (bar): (1) Casual Beachwear.
Small Security Room: (1) Dealer Visor (NOT located on map, where you rescue Kristin in "Lush-ious Lady").
Souvenir Kiosk outside Arena; (1) TIR Outfit.
From Fortune With Love: (2) Hawaiian Holiday Gear, Fortune City Grey Shirt.
Moe's Maginations: (1) Knight Boots (NOT required).
Bush Near Save Point (see map): (1) Flower Head Piece.
Hot Excitorama: (3) Blue Oyster Biker Outfit, Flip Flops, Mesh Party Wear.
(*) To Access the KokoNutz Locked Room You must arrive some time after 6am on day 3 (around case 4-1). The door should be marked "Tape It or Die". The door will become locked again after 12pm. If the door is locked and it is the correct time then there are 5 or more survivors currently spawned, there needs to be 4 or less spawned to open this door.
Try the following to fix this:
-Return to the safe room with any survivors you have(or murder them).
-Go to all active survivor missions and save (or murder) the survivors.
-Go to the Atlantica Casino and murder (or save) the 3 survivors playing high-stakes poker in the large northern room, they are not listed as an active mission but count towards the 8 survivor limit.
-Go to the Fortune Park entrance to the Atlantica Casino and save (or murder) Janus. He is not listed as an active mission but count towards the 8 survivor limit.