Rimmel vs Smashbox vs Jillian Dempsey Kohl Liners Compared

We compare three kohl pencils head to head: the budget Rimmel Exaggerate Eye Definer, the self sharpening Smashbox Always Sharp Kohl, and the clean beauty Jillian Dempsey Khol with sharpener bundle. All three promise intense, blendable kohl color with real staying power.
| Factor | Jillian Dempsey Khol Eyeliner in Rich Br | Rimmel Exaggerate Waterproof Eye Definer |
|---|---|---|
| Format | Retractable pencil | Self sharpening pencil |
| Shade tested | Earl Grey | Penny Lane |
| Pigment intensity | High | High |
| Smudge window | 60 seconds | 45 seconds |
| Waterproof | Yes | Yes |
| Built in sharpener or smudger | Smudger tip | Self sharpening cap |
| Price tier | Budget | Mid range |
| Best for | Everyday smoky eyes | Hassle free sharpening |
Our Verdict
Choose Rimmel Exaggerate if you want excellent kohl performance at a drugstore price with a handy smudger. Choose Smashbox Always Sharp if you hate carrying sharpeners and want the clever self sharpening cap. Choose Jillian Dempsey if clean, naturally derived ingredients matter and you prefer rich brown over black. For most shoppers, Rimmel delivers ninety percent of the experience for a fraction of the price.
More Top Picks in This Category
Not sold on either of these two? Here are more bestselling options worth considering.

Best for: Hassle free kohl with self sharpening precision
Smashbox Always Sharp Kohl Liner in Penny Lane
- Self sharpening cap keeps tip precise
- Waterproof kohl pigment
- Penny Lane warm bronze shade
- Creamy blendable formula
Pros
- Always a sharp point without a sharpener
- Unique warm shade flatters many eyes
- Good waterproof staying power
Cons
- Higher price than drugstore kohl
- Self sharpening wastes some product
- Penny Lane is not a classic black
Chill soft kohl pencils in the fridge for ten minutes before sharpening. Cold kohl cuts cleanly instead of crumbling, which wastes less product and gives a sharper point. This trick matters most for the softest formulas, which are also the ones that waste the most in a warm sharpener.
Sharpening Systems Compared: Wood, Retractable, Self-Sharpening
The three pencils in this comparison represent the three sharpening systems, and each has a real tradeoff. Wood pencils like the Jillian Dempsey need a separate sharpener but give the sharpest possible point and the most control over tip shape. The cost is product waste: every sharpening shaves off usable kohl, and a cheap sharpener with a dull blade wastes even more. A good cosmetic sharpener with a replaceable blade is a required accessory, not an optional one.
Retractable pencils like the Rimmel Exaggerate never need sharpening, which is pure convenience, but the tip goes blunt faster and can never be restored to a fine point. Self-sharpening designs like the Smashbox Always Sharp split the difference: the cap sharpens the tip each time you close it, keeping a decent point without a separate tool, but the mechanism itself consumes product with every twist. For heavy kohl users, wood pencils are cheapest long-term despite the sharpener; for occasional users, the convenience formats win. The iconic retractable benchmark is covered in our Urban Decay 24/7 guide.
Travel changes the value math. A retractable pencil survives a makeup bag without a sharpener; a wood pencil needs the sharpener packed too, and sharpeners get confiscated or lost. For travel-only use, the convenience format wins regardless of per-use cost.
The Real Cost Per Use of Kohl Pencils
Sticker price misleads with kohl pencils because usable product varies wildly. A self-sharpening pencil contains less usable product than it appears once the mechanism's waste is counted. A wood pencil, sharpened carefully with a good blade, delivers more applications per dollar than any retractable. To compare honestly, track how many weeks each pencil lasts with your usage pattern; that is your personal cost per week, the only number that matters.
Usage habits dominate the math. Tightlining daily consumes a pencil in weeks; occasional weekend smoky eyes stretch one for months. Heavy-handed application doubles consumption without improving the result. The budget Rimmel wins the value crown in this comparison not just on price but on the retractable format's zero-waste design; no sharpening shavings means every millimeter is usable. Buy the format that matches your usage intensity, not just the lowest sticker price.
Removing Waterproof Kohl Without the Scrub
All three pencils here promise waterproof or long wear, which means removal needs a real method. Water-based removers barely touch waterproof kohl; scrubbing with them pulls lashes and stretches the delicate eye skin. The correct method is oil-based or dual-phase remover: soak a cotton pad, press against the closed eye for twenty to thirty seconds to dissolve the product, then sweep downward once. The waiting is the step that prevents the scrubbing.
Removal difficulty should factor into which pencil you buy. If you remove makeup nightly and hate the process, an easier-to-remove formula wins on pure quality of life, even if it wears an hour less. If your days involve swimming, tears, or twelve-hour wear, the removal effort is the price of the performance. Our waterproof eye pencil guide ranks formulas by real staying power, and the Charlotte Tilbury Feline Flick guide covers wing technique for when your kohl needs to stay sharp all day.
Want the Full Picture?
Technique Tips for Better Eye Looks
Whether you reach for the Smashbox Always Sharp Kohl Liner in Penny Lane or the other picks in this roundup, a few technique adjustments will make the product last longer and look cleaner. Remove eye makeup gently every night, because sleeping in it irritates eyes and weakens lashes over time.