Photograph - Donald Ziraldo, Michael Budman, Ross Rebagliati & others in Aspen, CO

A photograph of five people, some are identifiable, such as Donald Ziraldo, Roots Co-founder Michael Budman and Ross Rebagliati, Canadian professional snowboarder and Olympic gold medal winner for Men's Snowboarding at the 1998 Winter Olympics. On the back it is noted that this is Aspen Colorado in 1998. This may relate to the 1998 Winter Games as two people in the picture are wearing the Roots hat designed for that event.

Photograph - Deputy Post Master and Letter Carriers, 1910

A photograph of Stanley George Smith (deputy post master in bowler hat) and eight letter carriers. The photograph is dated 1910.

Photograph - Hamilton Killaly Woodruff with a Child on Rocking Horse

Black and white photograph, 16 cm x 11 ½ cm, of Hamilton Killaly Woodruff with a young child [Charles Woodruff Band?]. The child is sitting on a rocking horse and Hamilton is standing watching the child with his hat in one hand and his cane in the other.

Photograph - Julia Cleveland Woodruff

Black and white photograph, mounted on board, 7 cm x 4 cm, of Julia posing in a straw hat.

Tintype - Unidentified Young Female

One 3 cm x 2 cm tintype of a young woman’s face. She is wearing a hat in this picture.

Photograph - Young Boy holding Dog

A young boy in hat gloves and coat, holding a dog in front of a barn.

Photograph - Two Men looking at Dogs

Two men, side by side, with three dogs and a cat. There is a barn in the background. The one man in a hat and long coat appears to be Percy Band.

Photograph - Group of Children Outdoors

A photograph of a large group of children (7) with one adult male. The children are all dressed in winter attire and the man is dressed in a fur winter coat and hat.

Photograph - Woman Standing by a Large Tree Trunk

A woman wearing a hat and holding a small purse. She is standing next to a large tree trunk and there are benches behind her.

Photograph - Woman in Swimming Attire with Dog

A woman in swimming attire sitting on sand with her arm around a dog. The dog is also wearing a hat.

Photograph - Group of Women

A photograph of a group of five women standing together with arms around eachother. They are outdoors and one of the women is wearing a hat.

Postcard - "Hello Boys"

A postcard with an insect illustration wearing a top hat and suit. The handwritten note on the front reads "Don't you think that I look well and prosperous?". On the reverse of the postcard it reads "A Happy New Year", addressed to Miss M. Woodruff, 168 Ontario St., St. Catherines, Ontario, Canada. The stamp is U.S. postage and the postmark is for Grand Central Station N.Y.

Receipt from James Oliphant, Cap Maker to the Army, London, England

Receipt from James Oliphant, Cap Maker to the Army, London, England for a silk hat, Aug. 26, 1847.