| 2025-01-18 | Jimmy Carter was the first president regularly seen in these |
| 2024-07-08 | Pants that are often blue |
| 2022-08-24 | Clothes that may come ripped |
| 2020-03-24 | Casual Friday wear |
| 2017-03-23 | Form-fitting casual wear |
| 2017-02-10 | Wardrobe item for which Obama claimed he was "unfairly maligned" |
| 2016-10-18 | Guess things |
| 2016-09-05 | Article of apparel with styles found at the starts of 17-, 26-, 41-, 51- and 66-Across |
| 2015-10-23 | "Democracy in fashion," per Giorgio Armani |
| 2015-02-24 | Guess attire |
| 2010-11-08 | Wranglers, e.g. |
| 2009-09-30 | Casual wear |
| 2009-04-20 | Levi's, e.g. |
| 2009-04-18 | Wranglers, e.g. |
| 2002-02-14 | Casual attire |
| 1999-04-01 | Cutoffs, maybe, before they were cutoffs |
| 1998-12-20 | Informal wear |
| 1998-01-21 | Wranglers, e.g. |
| 1996-05-02 | Weekend wear |