The lone, brave orphan pitted against the cold, cruel world is a plot as old the tales of King Arthur. Annie, Oliver and the Little Princess were all orphans and their stories make great drama. As the costumier of such a piece of theatre, outfitting an entire orphanage can be a challenge. Luckily the average orphan on the street was unlikely to dress in the latest expensive fashions; and when making your own orphan costume, you can get almost everything you need from the local thrift store. In fact, the worse your orphan looks, the more sympathy she'll get.
Find a dress. It should have sleeves, a flared skirt and reach below the knees. Look for drab colours like brown, dusty rose and maroon in small prints or solids.
Find a pinafore, or an oversized, scoop-necked, sleeveless dress, shorter than the bottom-layer dress. This goes on over the dress. Or, make a pinafore from a pattern. Distress the fabric and add a couple of stains and patches.
Make bloomers from an old pair of white or grey leggings. Cut them off and add elastic.
Finish up with baggy socks or dark tights and high-top boots.
Dress your boy orphan in a long-sleeve, button-down shirt and with a pair of dark trousers. Old dress pant work great, but do not use jeans. Shorten them to about mid-calf and add a patches to knees, elbows or seat. Hold up the trousers with suspenders.
Wear high-top boots and baggy socks or bare feet.
Use a flat wool cap with a bill to keep your orphan warmer on those cold nights spent begging on the streets. This also adds pathos when held nervously in both hands.
Dirty costumes by dipping in coffee or adding stains with bleach, Petroleum jelly or paint. Fray sleeves and hems with sandpaper or a file. Nothing about these outfits should fit well or match. Everything should look like it was pulled from a pile of castoffs and hand-me-downs.