Curly hair doesn’t have to mean high effort. In fact, when you find the right cut and let your natural texture do the work, you can pull off a look that’s stylish, comfortable, and totally low maintenance. That’s exactly why messy medium-length curly hairstyles are catching on with men across Ontario—from Kitchener and Waterloo to Guelph and Cambridge. They’re easygoing, full of personality, and perfect for guys who don’t want to spend a ton of time styling every morning.

Why Medium Length is the Sweet Spot

For curly hair, medium length offers a perfect balance. It gives your curls enough space to form naturally without becoming unruly. Too short and your curls might spring up too tightly; too long and they can be harder to manage. Medium length gives you volume, texture, and flexibility—plus that effortless, slightly messy look that always feels modern.

Top Low-Maintenance Messy Curly Hairstyles for Men

1. The Shaggy Curly Layer Cut

This one’s all about movement. The layers are cut to encourage natural texture, and the length stays between your ears and jawline. It’s a relaxed, casual look that grows out nicely. All it takes is some curl cream and finger styling. Great for guys who want to look put together without looking too polished.

Picture Credit: https://mensflair.com/best-shag-haircuts/

2. Curly Fringe with Tapered Sides

Keeping the sides short and the top a bit longer with a curly fringe gives you shape and definition. The fringe frames your face and the texture keeps things interesting. You don’t need more than a little leave-in conditioner to keep the curls soft and separated.

Picture Credit: https://gatsby.com.my/mens-lifestyle/curly-hairstyles-for-men-and-how-to-care-for-them

3. Textured Curly Mullet

Yes, the mullet is back—but it’s modern and much cooler this time. Medium length on top, shorter sides, and natural curls flowing in the back. It’s edgy, fun, and low maintenance. Perfect for men who want something different that still feels wearable.

Picture Credit: https://www.saltgrooming.com/blogs/blog/modern-mullet-styles-for-men

4. Loose Mid-Length Curls with Soft Fade

This cut keeps your curls medium on top and blends them gently into a low or mid fade on the sides. It adds structure without taking away the messy, natural volume. It’s a favourite for anyone looking to balance sharp edges with soft texture.

Picture Credit: https://wellgroomedgentleman.com/the-gents-journal/curly-hair-fade/

5. The Grown-Out Curly Crop

If you’ve had a short crop or fade and are growing it out, this in-between style can actually be a look on its own. Let the curls sit loosely across your forehead and ears. A little layering on top prevents the puff and helps it fall nicely. Ask your men’s barber for medium length hair to shape it while keeping that undone feel.

Picture Credit: https://uk.fudgeprofessional.com/blog/tutorial/a-mens-guide-to-growing-out-hair/

Styling Tips Without the Fuss

The best part of these styles? They don’t need blow dryers or complicated routines. Wash your hair, towel dry gently, then use a small amount of product like curl cream, sea salt spray, or mousse depending on your texture. Air dry and let your curls shape themselves—messy is the goal. You’re not chasing perfection here.

Find a Barber Who Gets It

Not every barber is great with curls—so if you’re planning to get a messy medium length haircut, find someone who understands how to shape curls properly. A good barber in Kitchener will know how to layer and balance your hair to get that easygoing shape that grows out well and stays low maintenance between cuts.