Our elementary does a basket raffle every Nov/Dec during Breakfast with Santa. Here are some baskets we've had in the past:
MLB or NFL- clothing with the logos (t-shirts/sweatshirts/hats/jackets/socks), football/baseball (signed is even better!), items to cheer the team on like pennant/pom-pom/foam hand, beverage or bar items with team logo, tail gating items (condiments, hot dog holders, beverage containers w/team logo, mini portable bbq grill, can huggies), blanket w/team logo, soft-sided cooler w/team logo, umbrella w/team logo, tickets to sports game
Family Game Night - board games, DVD games, snacks, pizza gift certificates, card games, bean bag chair, puzzles, coasters, drinks or drink mixes
Summertime Fun- popsicle maker, mini snow cone machine w/syrups, beach towels, flip-flops, sunscreen, sidewalk chalk, pool toys, pool floats, ice cream maker, sunglasses, gift certificate for local ice cream place, smoothie machine and mix, picnic basket, plastic picnic ware (plates, cups, napkin/silverware basket, condiment containers), beach chair, beach umbrella, fabric chair cover for chaise lounge, Razor
scooter, sun visor, gift certificate to ride go-karts or play mini golf, hula hoop
Wii - Wii game system, Wii games, gaming chair, additional controllers or accessories
Nintendo DS - DSi or DSxl or DS3D, games, carry case/accessories
Hamster - Cage, bedding, food, water bottle, pre-paid certificate to local pet store for hamster
Baking - jelly roll pan, bundt pan, loaf pan, brownie pan, cupcake pan, tins to store baked goods, mixes - brownie, cake, bread, layered cookie mix in a jar, sprinkles, icing, chocolate or other flavor chips, canned milk, coconut, brown sugar, flour, sugar, rolling pin, double boiler, candy melts, candy molds, oven mits/pot holders, apron, trivet, cookbook, nuts, bread basket, gift certificate for cooking/baking class or cake decorating class, recipe cards, recipe card holder, cookbook stand, spices, spice rack, cookie cutters, cupcake wrappers
Winter Fun - mittens, hats, scarves, hot chocolate, mugs, marshmallows, snowball mold, sled, heated socks, slippers, tea, robe, Snuggie, blanket, soup mix and soup bowl, cornbread mix, chili, crossword/seek and find books, puzzles, gift certificate to go ice skating
Crafts - suncatcher kit, stepping stone kit, modeling clay, paints and brush, sand art, markers, crayons, tissue paper, pipe cleaners, beads, yarn, mini sewing machine, card stock, glue, scissors - regular and shape cutters, punches, scrapbooking kits, scrapbook album, stickers, eyelets/brads, ribbon, craft organizer/containers, photo storage box, coloring books/activity books, foam sheets, foam shapes/letters, various craft kits from Michael's or Hobby Lobby
Movies - popcorn and popcorn containers or bowls, other snacks and candy, drinks or drink mixes, pizza gift certificate or pizza crust mix/sauce, bean bag chair, floor or body pillow, DVDs, movie posters, TV Trays, portable dvd player and headphones, projector
Pets- dog/cat bed, collars, treats, litter, food - dry and canned, toys, brushes, food and water bowls, leash, pet tags, pet clothes - sweater, raincoat, halloween costume, hygiene supplies (nail cutters, fur trimmers, shampoo, wipes, deodorizing spray), vitamins, gift certificates to local pet store/vet/wash service, doggie waste bags
Bath and Body - lotion, powder, body spray, nail polish, nail grooming kit, robe, hair wrap, terry body wrap, nice towels, pumice stone, bath salts/bomb, bubble bath, lip balm, candle, soap or shower gel, bath puff, back scrubber, neck rest for tub, book holder for tub, bath mat, hanging toiletry bag for travel, eye pad, make-up bag or train case, lighted mirror, body scrub, shower radio, spa sounds dvd, neck or body wrap (the kind you can microwave to warm)
Gift Certificates - can use a theme like restaurants or just buy from different vendors
iPod - iPod, case/accessories/speakers, gift certificate to buy songs
Sports- soccer ball, baseball, basketball, football, frisbee, tennis balls/raquet, jump rope, bicycle, hockey, roller skates, ice skates, bat, baseball glove, knee/wrist pads, safety helmet, inline skates, scooter, sports water bottles, sweat towels, Gatorade or sports drinks, skateboard, golf balls/bag/putters, gift certificate for time in local batting cage or golf course or sports lesson, tickets to sporting game/event
Gardening - seeds, watering can, garden gloves, knee pad, garden cart, sun hat, bulbs, trowel/rake/bulb planter, garden decor (statue, stepping stones, solar lights), gift certificate to local garden store or Lowe's/Home Depot, bird fountain, bird feeder with food, shephard's hook, rain stick, outside thermometer, flower pot, plant food
Books - chapter books, picture books, coffee table books, cookbooks, history books, crossword books, Soduku books, book covers, bookmarks, clip-on reading light, seek-and-find books, e-reader like Nook or Kindle, cover for e-reader, subscription or gift certificate for books for e-reader, books on tape/DVD
Princess - dress up shoes and clothes, kid make-up, wand, crown, Disney princess themed items (toys, brush, mirror, hair accessories, beach towel, etc.)
Superheroes - Batman, Superman, Spiderman, Hulk, Transformers - anything with that theme (toys, socks, hats, puzzles, cup, toothbrush, etc.)
Camping - hot dog/marshmallow forks, skewers, tent, camp chair, dutch oven, pie irons, camp recipes, lantern, camp shower, charcoal chimney, s'mores (graham crackers, marshmallows, chocolate bars), cooler, sleeping bag, citronella candles, weather/camping radio
I don't know if you plan on buying everything or asking folks to donate. Each teacher picks a theme for their classroom and families are asked to donate items to that theme. Or, you can donate money for PTO to buy items. Where Wii, iPod, Hamster, DSi and gift certificates are themes, the families are asked to send money only so that the game systems can be bought with necessary supplies - or random gift certificates. Some items really do come in baskets, but others are wrapped in a "container" from that theme. For example, items can be wrapped in a sled, in a dog bed, etc.
Hope this helps!