How to Grow Out Your Hair Without the Awkward Phase

Growing men’s hair longer sounds simple until the in-between weeks. A little planning makes the whole journey look intentional.

Why the awkward phase happens

Hair grows at different rates in different areas, so without maintenance the sides puff out, the back creeps over the collar and the whole thing loses shape. The fix is counter-intuitive: keep visiting the barber while you grow it out.

A simple roadmap

Weeks 1–6

Resist the urge to cut. Let the top gain length while you tidy only the neckline.

Weeks 6–12

Ask for light shaping on the sides so they lie flat instead of flaring. This is where most men give up — don’t.

Months 3–6

Start blending the layers so the top and sides grow into one length. A small amount of product helps train the hair.

Habits that help

• Use a conditioner — longer hair needs more moisture.
• Sleep on a smoother pillowcase to reduce breakage.
• Book a shaping trim every five to six weeks, not a cut.

Tell your barber the end goal at the very first visit so every trim moves toward it. A barber who handles regular men’s haircuts in Chicago will map the grow-out with you rather than just taking length off. If you are between barbers, Artur’s Barber Shop is a good place to start.