How to Grow Your Hair Out
Without It Looking Messy
The awkward in-between phase is where most men give up. Here's how to get through it looking intentional the whole way.
By Jessica Hamilton — Master Stylist & Creative Director
Growing your hair out sounds like it should mean "stop cutting it" — and that's exactly why most men bail during the awkward months. The counterintuitive truth: growing it out well requires regular trims and active styling, not neglect. Here's how to move through each phase looking deliberate rather than unkempt.
Why You Still Need to Cut It
Hair doesn't grow evenly — the sides and top reach awkward lengths at different times, so an untouched grow-out looks shapeless and mullet-ish fast. Regular shape-up trims every 4–6 weeks keep the proportions balanced and remove split ends, so the length you're gaining actually looks good. You lose a little length each trim, but you gain shape — a fair trade.
The Stages (and How to Survive Each)
| Stage | The challenge | What to do |
|---|---|---|
| Weeks 0-6 | Losing your old short shape | Keep the sides tidy, let the top lead |
| The awkward middle (2-4 months) | Sides flick out, top isn't long enough | Product to control flicks; consider a light taper; push through |
| 4-6 months | In-between length, ears covered | Regular trims for shape; start styling with length |
| 6+ months | Real length to work with | Layer it, find your style — flow, medium, longer |
Styling Through the Grow-Out
- Control the sides — when they flick out over the ears, a light product or a small taper tames them without losing the project.
- Use a cream or light clay to add control and direction (see product guide).
- Push it back or to the side rather than letting it sit wherever it lands.
- Embrace the phases as styles — the in-between stages are legitimate medium looks, not just waiting.
- Learn to blow-dry — a little root lift and direction transforms grown-out hair (or style heatless).
Realistic Timeline & Health
- Hair grows about half an inch a month — so shoulder-length from short is roughly a 1.5–2 year project.
- You can't speed it up much — support it with enough protein, gentle handling, and not over-washing.
- Trim split ends — damaged ends break off and make it look like it's not growing.
- Keep it healthy — longer hair is older hair, so condition well (see hair & scalp care).
- Have a target style in mind — showing your barber the end goal helps them trim toward it.