How to Grow Out Your Hair (Men): The Awkward Stage

Growing out a short haircut? Plan the in-between shape, protect the length you need, and manage styling and washing through the awkward stage.

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Illustration.

Growing out a short haircut is easy to start and harder to stick with when the sides puff out or the fringe falls into your eyes. The answer is not a fixed calendar or a promise that every stage will look good. It is a plan for the shape you want, a barber who understands that plan, and styling that works with the length you have now. The experiences below are individual growers’ reports, alongside Regal Gentleman’s barber guidance.

The short version:

  • Timeline: months, not weeks: hair averages about half an inch a month with individual variation, and one grower’s short-to-long report was about 8 months
  • Trims: agree which areas need to keep their length; a cleanup is different from restarting your short haircut
  • Survival kit: hats or hair bands, a styling product suited to your finish, and a barber who knows the goal
  • Texture surprise: your hair may behave differently at length than it ever did short

Check Baxter Clay Pomade on Amazon

How long it actually takes

Regal Gentleman’s grow-out guide gives roughly half an inch a month as a general growth reference. Starting length, desired style and individual growth make the overall timetable different for each person. In a May 2025 r/AskMen thread, u/calgarywalker described his own short-to-long transition:

Takes about 8 months to go from short to long. Mentally prepare yourself for that transition period.u/calgarywalker, r/AskMen, May 2025

Eight months is his report, not a deadline for your hair. Regal Gentleman makes the more useful point: choose an end style, then work out what needs to grow to reach it. You might also reach an in-between length you like. Keep a picture of that shape if you want the barber to recreate it rather than assuming longer is always the goal.

The awkward stage, and why growers say not to fight it

In a May 2024 r/malehairadvice discussion, u/anonymoustricho described a curtain-cut route through the transition:

Illustration of three side profiles of the same man showing hair growing out from short, through a medium awkward stage, to long, with arrows between the stages.
Illustration.

You can’t really skip it. The only way to do so would really prolong the process.u/anonymoustricho, r/malehairadvice, May 2024

His approach was to keep the back shorter while the front and sides grew toward curtains, then sweep the front back and let the lengths even out. That is one route, not a rule that every grower should keep trimming the same areas. A starting cut with very short sides needs a different plan from one with a short fringe and a longer back.

Trims during grow-out: yes or no

Regal Gentleman recommends an in-between haircut rather than assuming a barber visit means taking a lot of length off. Its examples include cleaning around the ears and neck and agreeing which uneven areas need to catch up. If you are growing out a short-sided cut, that might mean leaving the sides alone while changing another part of the shape. There is no universal instruction to trim the sides and protect only the top.

That distinction also changes the thinning question. The same guide advises against thinning while growing toward an even long length, because it creates more different lengths to catch up. Do not ask for thinning as an automatic cure for puffiness. Ask the barber whether shaping is compatible with your target style, and agree what length can go before the scissors come out.

Get your barber to advise on which areas in the hair may need more work or that may be slightly uneven from your previous shorter haircut.Regal Gentleman, grow-out guide

The guide does not set a universal return interval. Discuss the next visit in terms of the areas you are growing and the shape you are trying to keep. For recovery after a cut you did not want, our bad-haircut guide covers a different problem.

Styling through the middle months

The practical ideas in two grower discussions are less complicated than the timelines:

Washing and scalp care while growing

Longer hair needs a different routine than a short cut, and the dermatologists at the American Academy of Dermatology have published guidance that maps directly onto grow-out:

  • Match shampoo frequency to your scalp. Straight hair with an oily scalp can warrant daily shampooing; dry, textured, curly or thick hair needs it far less.
  • Shampoo the scalp, not the lengths, so you clean away oil and buildup without over-drying the hair itself.
  • Condition after every wash. For fine or straight hair, the AAD says to apply conditioner to the ends; for dry or curly hair, the full length.
  • Be gentle with wet hair. Use a wide-tooth comb instead of a brush: for thick or curly hair, comb in the shower before rinsing out conditioner; for straight hair, let it dry a bit first. Wrap with a towel or t-shirt rather than rubbing.

Our hair-washing guide covers the routine in more detail. Keep this part of grow-out about washing, conditioning and gentle handling, rather than looking for a styling product that promises to change the rate of growth.

What to tell your barber

Bring clear pictures of the end goal and explain that you want an in-between shape, not the finished long haircut today. Regal Gentleman recommends telling the barber what annoys you in daily styling, including the section that sticks up or will not sit where you want it. That gives the conversation something more useful than “make it tidy”.

A clearer request is: “I’m growing toward this style. Which areas need to keep their length, and what can we clean up without losing that plan?” This is a conversation starter, not an instruction to remove the same section on every head. Our barber conversation guide has more on explaining a goal.

Expect to reassess the shape as it grows. In a June 2026 grow-out post, the poster described discovering wave in hair he had thought was straight when short. Regal Gentleman likewise recommends working with the way your hair wants to fall rather than forcing a slick-back against it. A picture is a reference for the conversation, not a guarantee that a different texture will fall the same way.

Watch an in-between haircut

Regal Gentleman’s accompanying video follows Joseff, who wanted to grow toward a Jax Teller or Captain America-inspired longer style. The published guide explains why the team suggested an in-between haircut rather than abandoning the grow-out.

Also worth a look

Also worth a look: Suavecito Original Hold

For a more defined, shiny shape, Suavecito describes Original Hold as water-based, with medium hold and medium shine. It is a different finish from the matte Baxter clay, rather than a claim that one works better for every grow-out.

Check Suavecito Original Hold on Amazon

Also worth a look: STMNT Matte Paste

Another matte styling option to compare with the Baxter clay. Choose a finish you want to wear now rather than treating a styling product as a way to skip the grow-out. Our pomade, clay and wax guide explains the styling categories.

Check STMNT Matte Paste on Amazon

FAQ

How long does the awkward stage last? It varies with growth rate and starting cut. The May 2025 r/AskMen member quoted above put his short-to-long transition at about eight months. That does not establish the same timeline for a different starting cut or goal.

Should I trim my hair while growing it out? Agree a target shape first. Regal Gentleman recommends a cleanup that protects the areas which need to catch up, and advises against automatic thinning when growing toward an even long length.

How do I stop the sides from puffing out? Work with the direction your hair falls and a styling finish you like. Ask your barber which areas need to grow, rather than automatically thinning the sides.

Does cutting hair make it grow faster? No. Regal Gentleman explains that cutting the ends does not change growth at the root. A trim changes the shape and removes length; it does not speed up the process.

When can I tie it back? There is no fixed month; it depends on your starting cut and growth rate. One member’s entire method was “I would just wear a hat until it was long enough to tie.”