Kaywoodie was created in 1919 by Kaufman Brothers & Bondy (see KB&B). It is a brand of S. M. Frank & Co since March 1955.

The cloverleaf logo: the round logo (black cloverleaf in white circle or white cloverleaf in black circle) was first used in 1937. Up until the late 40's this logo was used on all of the upper grades pipes. The concomitant use of the plain white cloverleaf and the disk inlaid logo continued untill the early 80's.
Up until the late 1940's/early 50's, the logo was on top of the stem. After that the logo was moved to the side of the stem.

Kaywoodie seconds: Bentley US, Devonshire

 

05 should be the shape code (short shank billiard), and the 27 (1927) may be the production year. Push tenon design (pre-synchrostem) .

▲ Rock Ambera: Bakelite stem with appearance of amber. These pipes had a black cloverleaf.
More about the PAT. APP. FOR stamping

▲ KBB clover on the shank (prior to 1933).
No "PAT. APP. FOR" stamping would indicate the synchrostem patent was allready granted (1932) when this pipe was crafted.

The KBB Clover stamp on the shank indicates a pipe crafted in the old KB&B plant at Union City (NJ) prior to 1933.

Cloverleaf logo embedded in the shank. Shank embedded logos were stoped by 1938.

This pipe is stamped with a four digit number which situates its production year between 1931 and 1938.
More about the PAT. APP. FOR stamping

Period: 1928-late 1950's
"Made in England" Suntans have been produced more recently.

Period: 1928-late 1950's

Briar mouthpiece.
Period: 1952 to late 1960’s

The Campus Kaywoodie line was introduced in 1968.

A valve on the bowl's bottom (see detailed pics) is supposed to regulate the air stream.
Period: 1937-1938, 1948-1976
Same device: Dunhill Airstream, Passat

 

Pipe with a double-bore stem which is more durable if a smoker has a tendency to chew a stem.
Other "twin bore" pipes: Grand Master, Leonard's, Radice

More infos here: Smoking Metal

More infos here: Smoking Metal

More about Filtronic here: Smoking Metal

Early Flame Grains were stamped Flame Grain over top of Kaywoodie.
Prior to 1935 Kaywoodies never were stamped "Imported Briar"

▲ Briar pipe with a removable meerschaum inner bowl.

Characteristic feature: the lid (see enlarged view)
Cloverleaf on top of the stem
4-hole stinger, with drinkless stamped on it (see enlarged view)

 

The color of the stem and/or the finish of the bowl could change: see detailed view for three variants.
The issue with this model was the rhinestones which often came off the bowl.

This pipe was made in 1976 to commemorate the 200th anniversary of the independence of the United States.
See also the pipe commemorating the 200th anniversary of the French revolution.

The Mandarin line was produced from 1960 to 1967

 

▲ No markings on the shank.
Twin bowl model. Meerschaum pipe with two screew-in and interchangeable bowls made of meerschaum too.
Period: 1958 - 1968

▲  Among the seven Oversize finishes shown in the 1947 catalog, two were banded: the "Goliath" (Virgin finish) and the "Hercules" (Walnut finish). This pipe seems to be a "Hercules".

The Red Root is not a part of the original Kaywoodie line. It is a style of pipe that was introduced in 1976 by S.M. Frank after that company purchased Kaywoodie.

This line was introduced in 1977

▲ This pipe is stamped with a four digit number which situates its production year between 1931 and 1938. Because of the introduction of the "Imported Briar" stamping in 1935, the pipe could have been manufactured between 1935 and 1938.

Compare the stampings of these two pipes: Early Super Grains were stamped Super Grain over top of Kaywoodie.

In the early 80's the switch was made to a stamped outline of a cloverleaf logo.

 

English Kaywoodie pipe made by Oppenheimer pipes

English Kaywoodie pipe made by Oppenheimer pipes.
See also: "Checker" from Yello-Bole