合うかどうかこの帽子をかぶってみてください。

to come together; to merge; to unite; to meet; to fit; to match; to suit; to agree with; to be correct; to be profitable; to be equitable; to do ... to each other; to do ... together

indicates a question (sometimes rhetorical); or; whether or not; some- (e.g. something, someone); indicates doubt, uncertainty, etc.; emphatic prefix; suffix forming adjectives or adverbs; in that way

how; in what way; how about

this (something or someone close to the speaker (including the speaker), or ideas expressed by the speaker)

hat; cap

indicates direct object of action; indicates subject of causative expression; indicates an area traversed; indicates time (period) over which action takes place; indicates point of departure or separation of action; indicates object of desire, like, hate, etc.

to put on (one's head); to wear; to have on; to pull over (one's head); to crown (oneself); to be covered with (dust, snow, etc.); to pour (water, etc.) on oneself; to dash on oneself; to ship water; to bear (e.g. someone's debts, faults, etc.); to take (blame); to assume (responsibility); to shoulder (burden); to overlap (e.g. sound or color); to be similar; to be redundant; to be fogged (due to overexposure, etc.); to close; to come to an end; to get a full house; to sell out; to blunder; to bungle; to fail; to be deceived

to give; to confer; to bestow; to kindly do for one; to oblige; to favour; to favor