Ring & Brewer (Dallas) — 1956

Why don’t people dress like this anymore? (Even though I’m not altogether sure that they ever really DID.)

Lilt Party Curl Children’s Home Permanent — 1954

“NO PINCURLS.”

Carter’s Trigs — 1950

Probably a depiction of a father doling out his son’s allowance, but this ad campaign is fraught with double entrendres. Others can be seen here.

U.S. Gaytees Rain and Snow Shoes — 1948

Are you ready?

Weather Winky Sno-Suits — 1948

“What does your father do, Billy?”
“He makes Weather Winky Sno-Suits!”

McGregor Sportswear for Men and Boys — 1949 (Christmas)

This ad answers the age-old question “Do the socks match the vest?”

Eagleknit Hats — 1952

That squirrel better watch out. He might end up as the next trim on her hat!

Brown Shoe Company Robin Hood Shoes for Children — 1958

“Good for children’s feet.”

Carter’s Trigs — 1953

There’s a whole series of these ads. They’re all odd.

Chips Sports Tartans for Boys — 1950

“Exciting outfits that unlock a young boy’s yearning for something ‘different’” (walking stick not included).