Men with square face shapes often have strong, chiseled features — defined jawlines, broad foreheads, and equal width from cheek to jaw. It’s a masculine, confident look, but it also means not every hairstyle will naturally flatter the face. The wrong cut can make the face look boxy, while the right one enhances structure and creates balance.
This article breaks down 9 hairstyle options that work especially well for square-faced men. These styles bring contrast, lengthen or soften the appearance of strong lines, and give you an overall sharper look. Whether you prefer something short, professional, edgy, or longer and more laid-back, there’s a style that works with your face shape and hair type.
1. Textured Crop
The textured crop is perfect for men who want something modern and manageable. It adds volume on top with messy, choppy layers that break up the symmetry of a square face. The sides are usually faded or tapered, drawing attention upward and softening the jawline.
Picture Credit: https://www.pinterest.com/pin/591660469795593659/
This cut is low-maintenance and works well with a matte styling clay, especially helpful during colder Canadian seasons when humidity is low.
Visit a barber who knows this type of haircut to ensure the texture is cut to match your hair’s natural movement.
2. Side-Swept Undercut
This hairstyle contrasts shorter sides with longer hair on top that is swept to one side. The asymmetry flatters a square face by breaking up the straight lines and adding motion. It also lets you keep some length for styling flexibility.
Picture Credit: https://www.menshairstylestoday.com/side-swept-undercut-hairstyles/
If you’re looking to get pony haircut for men in Kitchener but aren’t ready to go that long, this is a stylish middle ground.
Use a lightweight wax or pomade to control the direction without making it look stiff, especially in high humidity.
3. Crew Cut with Mid Fade
A classic option for men who like to keep it clean, the crew cut works well for square faces when paired with a fade. The top is kept short, but with just enough length to brush forward or slightly to the side. The fade on the sides draws the eyes up and gives your features more vertical balance.
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Ideal for daily wear, this cut is also easy to maintain and won’t require much styling effort — great for busy Canadian mornings.
4. Medium-Length Quiff
The quiff is a bold and confident choice that adds height and volume to the top of the head. This added height can help lengthen the look of a square face, balancing out wide cheekbones or a strong jaw.
Picture Credit: https://manforhimself.com/mens-hairstyles/textured-quiff-with-high-hold/
To style a quiff properly, blow-drying is key. Use a volumizing spray or mousse for hold during colder months when hair tends to fall flat due to dry air.
5. Classic Side Part
The side part is a timeless, versatile haircut that suits almost every face shape — including square. By combing your hair to one side and creating a natural part, you introduce soft lines to counter the angular shape of your face.
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This style is especially effective if your hair has some wave or texture. Pair it with a light hold pomade for that natural, structured look.
6. Short Pompadour
The short pompadour gives a touch of vintage flair while keeping things masculine and clean. It adds volume to the top while keeping the sides tight and tapered. This balance elongates your face and shifts the focus away from strong jawlines.
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It’s best to apply a pomade or styling cream that adds shine and hold. Ask a barber who knows this type of haircut to avoid over-bulking the sides, which can exaggerate the squareness.
7. Loose Waves with Mid-Length
If you have naturally wavy or curly hair, letting it grow out a bit can be a great way to add softness to your overall look. Keep the sides slightly shorter while leaving the top and back around 3–5 inches long. This shape frames your face without adding more bulk to your jaw.
Picture Credit: https://www.pinterest.com/pin/33-versatile-mediumlength-hairstyles-for-men–209065607695355665/
This relaxed, low-pressure style is especially fitting for men who like a more laid-back, effortless vibe.
8. Tapered Fringe
A fringe, when styled correctly, works well to soften a strong forehead. This version of the cut keeps the fringe longer in the front while tapering the sides and back for structure. It offers contrast and softness at the same time.
Picture Credit: https://www.pinterest.com/pin/16888567444076391/
This style works well in colder months when wind and static can play havoc with more structured cuts. Using a lightweight cream can help manage the fringe without making it greasy.
9. Brushed-Up Style with Low Fade
Brushing your hair upward and back creates vertical movement, which helps lengthen the face. A low fade keeps the base of the cut clean and sharp while allowing the brushed-up top to shine. This creates a fresh, youthful silhouette, particularly effective if you’re in your 20s or 30s.
To keep the style intact throughout the day, use a Canadian winter-friendly styling powder or sea salt spray for lift.
If you have a square face shape, you’re already working with one of the most classically masculine facial structures. The key is to pick a hairstyle that complements those strong angles rather than emphasizing them too much. Styles with volume, texture, or asymmetry work especially well.
For best results, visit an expert who knows haircuts for such hair type and understands how your face shape, hair texture, and Canadian climate all play a role in the final outcome.
Whether you’re located in Kitchener or anywhere in South West Ontario, you deserve a cut that fits your features and style. Book your next visit at Stylish Barbershop and let’s find the perfect fit for your face shape.