| 100% | DRESSEDUP | 9 | Wore a tux, say |
| 92% | OVERDRESS | 9 | Wear a tux to a diner, say |
| 73% | DRESSEDUP | 9 | Wore a tux, maybe |
| 70% | INDISGUISE | 10 | Wearing a costume, say |
| 70% | DRAPE | 5 | Wear a sari, say |
| 70% | HATTED | 6 | Wearing a homburg, say |
| 66% | WIRED | 5 | Wearing a hidden mic, say |
| 65% | INCOG | 5 | Wearing a wig and shades, say |
| 65% | INDISGUISE | 10 | Wearing a wig and sunglasses, say |
| 64% | INCOG | 5 | Wearing a wig and dark glasses, say |
| 64% | PACE | 4 | Wear a hole in the carpet, say |
| 63% | PREPPY | 6 | Wearing a polo shirt and boat shoes, say |
| 62% | BRO | 3 | One wearing a lacrosse tank top, say |
| 62% | SHORN | 5 | No longer wearing a wool coat, say |
| 60% | FREEZE | 6 | Regret not wearing a coat, say |
| 60% | HIKER | 5 | One wearing a fanny pack and eating gorp, say |
| 59% | CAMERAREADY | 11 | Wearing makeup and a stylish outfit, say |
| 59% | NUDE | 4 | Wearing just a smile, say |
| 58% | ICANSEE | 7 | What someone wearing a 14-Down couldn’t honestly say |
| 58% | BERET | 5 | A hat worn by the Special Forces, say |
| 58% | HATHEAD | 7 | Hair matted from wearing a cap, say |
| 57% | STOODOUT | 8 | Wore red at a wedding, say |
| 56% | TEMPTFATE | 9 | Wear white to a chili cook-off, you might say |
| 56% | OUT | 3 | Inside ___ (wrong way to wear a shirt, say) |
| 55% | PROM | 4 | Where a teen may wear a tux |
| 53% | HATS | 4 | A person with lots of responsibilities is said to wear many of these |
| 50% | LOUD | 4 | Like neon-green plaid pants worn with a hot pink floral top, say |
| 49% | MOPED | 5 | Wore a puss |
| 49% | POUT | 4 | Wear a puss |
| 49% | POUTY | 5 | Wearing a scowl |