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Employee Compensation Plans - Additional Information (Details) |  |  |  | 12 Months Ended
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Feb. 24, 2016 shares | Jan. 28, 2016 shares | Jan. 06, 2016 shares | Dec. 31, 2015 USD ($) employee_compensation_plan shares | Dec. 31, 2014 USD ($) shares | Dec. 31, 2013 USD ($) | Dec. 31, 2012 | Dec. 31, 2011
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Number of employee compensation plans granted | employee_compensation_plan |  |  |  |  | 2 |  |  |  |
Term granted for options (in years) | [1] |  |  |  | 5 years | 5 years | 5 years | 5 years | 5 years
Options granted (in shares) | shares |  |  |  |  | 4,177 | 2,976 |  |  |
Maximum annual contribution under Defined Contribution Plan |  |  |  |  | $ 18,000 | $ 17,500 | $ 17,500 |  |
Employer contribution to Defined Contribution Plan |  |  |  |  | 1,600,000 | 1,200,000 | 1,300,000 |  |
Deferred bonus amounts |  |  |  |  | $ 8,300,000 | 8,600,000 | 8,500,000 |  |
Vesting period of deferred bonus |  |  |  |  | 5 years |  |  |  |
Company-owned life insurance policy designed to offset a percentage of the EDCP liability |  |  |  |  | 60.00% |  |  |  |
Deferred compensation plans cost |  |  |  |  | $ 8,600,000 | 11,400,000 | 17,800,000 |  |
Stock Appreciation Rights |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Compensation expense relating to the share-based awards |  |  |  |  | $ 1,800,000 | 380,100 | 4,100,000 |  |
Cost is expected to be recognized over a weighted average period |  |  |  |  | 2 years 3 months 24 days |  |  |  |
Aggregate intrinsic value of OARs outstanding and expected to vest |  |  |  |  | $ 499,900 |  |  |  |
Liability related to the OARs |  |  |  |  | 1,600,000 |  |  |  |
Total unrecognized compensation cost |  |  |  |  | 2,100,000 |  |  |  |
Stock Appreciation Rights | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting period under share based payment |  |  |  | 5 years |  |  |  |  |
Number of OARs | shares |  |  |  | 491,160 |  |  |  |  |
Employee Stock Option |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Compensation expense relating to the share-based awards |  |  |  |  | $ 69,900 | 133,600 | 158,200 |  |
Cost is expected to be recognized over a weighted average period |  |  |  |  | 2 years 6 months |  |  |  |
Aggregate intrinsic value of options outstanding |  |  |  |  | $ 171 |  |  |  |
Aggregate intrinsic value of vested options |  |  |  |  | 43 |  |  |  |
Aggregate intrinsic value of options that are expected to vest |  |  |  |  | 163 |  |  |  |
Unrecognized compensation cost related to unvested share-based compensation |  |  |  |  | 44,500 |  |  |  |
Employee Stock Option | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting period under share based payment |  | 4 years 6 months |  |  |  |  |  |  |
Options granted (in shares) | shares |  | 3,907 |  |  |  |  |  |  |
Class A Stock | Restricted Stock |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Aggregate intrinsic value of ESP awards outstanding |  |  |  |  | 21,900,000 |  |  |  |
The aggregate intrinsic value of ESP awards that are expected to vest |  |  |  |  | 21,100,000 |  |  |  |
Compensation expense relating to the share-based awards |  |  |  |  | 4,600,000 | $ 5,600,000 | $ 5,000,000 |  |
Unrecognized compensation cost related to unvested share-based compensation |  |  |  |  | $ 9,500,000 |  |  |  |
Cost is expected to be recognized over a weighted average period |  |  |  |  | 1 year 8 months 12 days |  |  |  |
Number of shares of Class A Stock available | shares |  |  |  |  | 882,401 |  |  |  |
Equity Incentive Plan |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Expiration period |  |  |  |  | 6 months |  |  |  |
Equity Incentive Plan | Second Anniversary |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  |  |  | 25.00% |  |  |  |
Equity Incentive Plan | Third Anniversary |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  |  |  | 25.00% |  |  |  |
Equity Incentive Plan | Fourth Anniversary |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  |  |  | 25.00% |  |  |  |
Equity Incentive Plan | Six Months Before Expiration |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  |  |  | 25.00% |  |  |  |
Equity Incentive Plan | Class A Stock | Vesting Period Five Years |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Term granted for options (in years) |  |  |  |  | 5 years |  |  |  |
Employee Share Plan | Minimum |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting period under share based payment |  |  |  |  | 3 years |  |  |  |
Employee Share Plan | Maximum |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting period under share based payment |  |  |  |  | 5 years |  |  |  |
Oppenheimer Holdings Inc. Stock Appreciation Right Plan |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting period under share based payment |  |  |  |  | 5 years |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Number of shares awarded | shares |  | 355,833 |  |  |  |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | Non Employee Director | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Number of shares awarded | shares |  |  | 28,000 |  |  |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | July 27, 2016 | Non Employee Director | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |  |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | July 27, 2017 | Non Employee Director | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |  |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | July 27, 2018 | Non Employee Director | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |  |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | July 27, 2019 | Non Employee Director | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |  |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | Vesting Period Five Years | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting period under share based payment |  | 5 years |  |  |  |  |  |  |
Number of shares awarded | shares |  | 257,500 |  |  |  |  |  |  |
Stock Incentive Plan 2014 | Class A Stock | Vesting Period Three Years | Subsequent Events |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Vesting period under share based payment |  | 3 years |  |  |  |  |  |  |
Number of shares awarded | shares |  | 98,333 |  |  |  |  |  |  |
Executive Deferred Compensation Plan and Deferred Incentive Plan |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Company's deferred compensation liability |  |  |  |  | $ 49,000,000 |  |  |  |
CIBC Deferred Compensation Plan |  |  |  |  |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |  |  |  |  |
Company's deferred compensation liability |  |  |  |  | $ 14,300,000 |  |  |  |
[1] | The expected term was determined based on actual awards.

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