20+ First Day of School Hairstyles for Boys this 2025

Cindy Marcus
Cindy Marcus Hairstylist, Editor-in-Chief

Every kid wants to walk in on that first day feeling fresh, and honestly, getting the right cut or style can make all the difference. Parents, the key is picking a style that’s not just clean, but also low-maintenance—because nobody wants to battle cowlicks or hat hair before school every morning. Fades, textured crops, and even longer styles can look sharp as long as you use a matte finish styling product so the hair doesn’t look greasy under classroom lights. Remember, don’t skip the neckline clean-up—details like this are what set a style apart, even for the youngest guys. Ready to see which looks will actually stick past picture day? Check out all the styles you’ll want to screenshot before heading to the barbershop.

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Classic boys school haircut with side-swept top and traditional taper

#1 Neat Side Sweep with Classic Taper

Timeless and tidy, this side-swept cut with a taper is a go-to for picture day or back-to-school season. It’s styled with a gentle part and softly combed-over top, perfect for straight or wavy fine hair. The taper around the neckline and ears is scissor-blended, which keeps the look polished but low-fuss. Best suited for more conservative dress codes or boys who like structure without strong fades.

First day of school boys curly haircut with high volume top and low taper fade

#2 High Volume Curls with Taper Fade

Great for thick, naturally curly hair, this high-volume top with a low taper fade keeps curls bouncy but controlled. The fade behind the ears and neckline gives a clean edge, making mornings easier for active boys. It suits round or oval faces best and works well for boys who don’t mind a little styling product. One tip—make sure curls stay hydrated to avoid frizzing mid-day.

Boys faux hawk school hairstyle with spiked top and faded sides

#3 Spiked Faux Hawk with Fade

High-energy and playful, this faux hawk with a fade is great for boys who want to stand out on the first day. It’s best on medium to thick hair with a bit of grit—fine hair may not hold the height. The sides taper in tight, giving clean edges that don’t need much upkeep. It’s a bold choice but still easy to style with a dab of matte wax in the morning. Great for oval or rounder face shapes.

School hairstyle for boys with tousled crop and natural red hair texture

#4 Tousled Crop with Natural Texture

Soft and touchable, this tousled crop highlights the natural texture and color beautifully. Works best for fine to medium-density hair and especially suits lighter shades where texture shows. The top is left slightly longer for movement, with short tapered sides that blend well without a harsh fade. It’s great for boys who want to keep some personality without too much styling time. Pairs well with freckled or fair complexions.

Medium-length boys school haircut with layers and natural feathered texture

#5 Layered Medium Cut with Natural Flow

Balanced and versatile, this medium-length cut features soft layers that fall effortlessly around the face. Ideal for boys with wavy or straight hair and medium to thick density. The layered finish gives a feathered, lightweight movement without it getting in the way during class or play. Great for boys who prefer to skip styling products—just brush and go. A great choice for square or oval faces.

Curly boys mop top hairstyle with natural volume for school

#6 Curly Mop Top with Soft Volume

Light and airy, this curly mop top is a great option for boys with tight ringlets or springy curls. The length allows the curls to stack naturally, giving bounce and volume without needing much styling. It’s especially flattering for heart-shaped or angular faces, and works best on thick, naturally curly hair. Maintenance-wise, just a leave-in conditioner and finger scrunch is all you need most mornings.

Short blonde curly boys haircut for school with tapered sides

#7 Blonde Curls with Tapered Sides

These blonde curls are trimmed just enough to stay controlled while showing off the natural texture. The top is left curly and voluminous while the tapered sides offer structure and ease. Ideal for boys with fine to medium curly hair and lighter tones where curl definition really pops. Great for warmer months or active school routines—lightweight, breezy, and low-maintenance with curl cream.

Modern boys school bowl cut with soft texture and layered bangs

#8 Classic Bowl Cut with Modern Texture

This isn’t your 90s bowl cut—it’s got modern flair with its textured layers and relaxed flow. Great for boys with thick, straight hair that lays smoothly. The bangs sweep naturally across the forehead without being too blunt, and the overall shape is round but not rigid. Works best on square or oval faces, and it grows out evenly, making it parent-approved for less frequent trims.

Boys tousled textured haircut with short sides for back to school

#9 Tousled Texture with Short Sides

Casual but sharp, this tousled texture cut features scissor-cut layers on top and neatly tapered short sides. It’s perfect for boys with straight to slightly wavy hair who want an easygoing but styled look. The top has a light choppy finish for movement, with no harsh lines—great for oval or round face shapes. It air-dries well and only needs a small dab of light hold cream if you’re short on time before the bell.

High fade boys haircut with tight curls and lined-up hairline

#10 Tight Curls with High Fade

Fresh and defined, this tight curl style is shaped into a rounded top with a sharp high fade and clean line-up. Ideal for boys with naturally coily or tight 4A-4C curls and high density. The contrast between the crisp fade and the textured top keeps the style structured and breathable—perfect for staying cool and confident on the first day. The cut enhances curl shape while minimizing daily maintenance.

Modern boys back to school haircut with choppy fringe and high fade

#11 Choppy Fringe with High Fade

Sharp and modern, the choppy fringe gives this cut an edgy look while the high fade keeps the sides neat and crisp. Best for straight to slightly wavy hair with medium thickness. The fringe is point-cut for uneven texture and a tousled effect that still frames the face nicely. It’s a bit more stylized, so ideal for older boys or those who like experimenting with product and shape.

Boys undercut school hairstyle with brushed back volume and faded sides

#12 Brushed Back Undercut

This brushed-back undercut gives a sharp silhouette with a touch of volume and flow. It works best on straight or slightly wavy medium-density hair. The undercut sides are faded close while the top is left long and shaped with a round brush or blow dryer for lift. It’s a standout look that feels grown-up, but keep in mind it needs daily styling to keep that height intact throughout the school day.

Boys long curly school hairstyle with shoulder-length ringlets and volume

#13 Shoulder-Length Ringlets

Soft and free-flowing, these shoulder-length ringlets show off natural curl definition without sacrificing length. Great for medium to thick curly hair and oval or oblong faces. The cut is kept balanced with soft layering around the bottom to prevent bulk and allow movement. It does require some product—usually leave-in conditioner or curl cream—to keep frizz at bay and define curls for picture-ready days.

Slick boys hairstyle for school with defined side part and mid fade

#14 Slick Side Part with Mid Fade

This slick side part paired with a mid fade gives off a polished look that’s still playful. Great for boys with straight, fine to medium hair, it holds up well with a bit of pomade and comb work. The mid fade gives enough contrast without being too harsh, which suits rounder and longer face shapes nicely. It’s structured, but still allows some freedom of movement throughout the day.

First day school haircut for boys with short textured crop and low skin fade

#15 Textured Crop with Low Fade

Short and practical, this textured crop with a low fade keeps things neat without being too serious. The top is cut with point-cutting techniques to add roughness and depth, and the sides fade gradually for a clean finish. It’s best for fine to medium-density hair and works on most face shapes. A dab of matte pomade makes it school-ready without looking overdone. Super manageable for busy mornings.

Wavy boys medium shag haircut for school with layered natural texture

#16 Medium Shag with Natural Waves

Easygoing and full of movement, this medium shag is perfect for wavy hair with a softer texture. The layers are long enough to frame the face but still short enough to avoid tangles throughout the school day. Great for boys with oval or heart-shaped faces and medium-density hair. This style has that “unstyled but intentional” feel and works best when air-dried with a touch of curl cream.

Boys messy spike haircut for school with choppy layers and textured styling

#17 Messy Spikes with Choppy Layers

Bold and casual, these messy spikes with choppy layers give off a fun, carefree energy. Ideal for medium to thick straight hair, the disconnected layers on top offer tons of movement while the sides stay cropped close for shape. The best part is it doesn’t have to be perfect—actually looks better the messier it gets. Just a bit of wax or paste and you’re out the door. Works especially well for active, expressive kids.

First day school hairstyle for boys with voluminous quiff and soft taper fade

#18 Voluminous Quiff with Taper Fade

Stylish and confident, this voluminous quiff with a gentle taper fade balances flair with functionality. It’s ideal for thick, straight to wavy hair and suits oval and rectangular face shapes well. The quiff adds height and character up top, while the faded sides keep it school-appropriate. Requires a bit of product and blow-drying, so it’s best for boys who like a morning routine—or don’t mind a parent helping out.

Simple boys school buzz cut hairstyle with uniform short length

#19 Clean Buzz Cut

Low-maintenance and always neat, this clean buzz cut is perfect for busy mornings and active school days. It suits all hair types and densities, but especially works for boys who want a no-fuss routine. There’s no styling required, just a trim every few weeks to keep it sharp. It’s also a great option for kids with sensitive scalps or those who dislike combing. Minimal upkeep, maximum ease.

Messy spiked school haircut for boys with short layered top and choppy ends

#20 Spiky Layers with Tousled Finish

Fun and casual, this spiky layered cut has a choppy texture that gives it a tousled, energetic feel. It works well on straight to slightly wavy hair, especially for boys with fine to medium density who want some volume without going too wild. The back and sides are short but not faded, making this easy to grow out. This is a great option for creative boys who don’t want anything too stiff or polished.

School comb over hairstyle for boys with hard part and sleek gelled finish

#21 Sleek Comb Over with Hard Part

Sharp and polished, this sleek comb-over with a hard part is perfect for boys who like to look put together. Ideal for straight, fine to medium-density hair, it features a skin fade on the sides and a defined part shaved in. Great for rectangular or longer face shapes. Just know it needs daily product to hold, so not ideal for kids who fuss with their hair a lot. Looks great with a collared shirt or uniform.

Boys school haircut with textured crop top and high skin fade sides

#22 Textured Crop with Skin Fade

Edgy yet manageable, this textured crop with a high skin fade adds modern flair without high maintenance. Best for boys with straight or slightly wavy hair and medium to thick density, the top is scissor-cut and layered for texture while the sides are buzzed to skin for contrast. It flatters heart or angular face shapes. The cropped length makes it practical for sports days and classroom focus.

Boys side-swept undercut hairstyle for school with clean fade and neat parting

#23 Classic Side-Swept Undercut

Neat and timeless, the side-swept undercut offers structure without feeling too formal. This style works best on straight, medium-density hair, and especially suits square or oval faces. The deep side part and clipper-faded sides mean less bulk, but you’ll want a bit of pomade or gel to keep the top tidy all day. Perfect for boys who want a clean, school-appropriate look with just enough style.