The most common and most likely answer to this crossword clue is the 5 letter word DERBY
I've seen this crossword clue in The Daily Telegraph
D
E
R
B
Y
More clues leading to the result DERBY
- The German Times? It's a classic
- Communist rejected by town
- German’s the next to race
- Bowler in match between close rivals
- Revolutionary communist near to getting authority in the Midlands
- Order Byron to host local football match
- Midlands’ bowler
- Unknown quantity produced upset in horse race
- Bowler embarrassed about extra mostly
- Local game for a US hat
Buddy explains!

The straight part
We know that "A classic/hat worn by Americans" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case a classic/hat worn by americans = derby.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.
What does DERBY mean?
DERBY noun- Any of several annual horse races.
- (by extension) Any organized race.
- A bowler hat.
- A local derby.