Haircuts are really peculiar little identity signs. Maybe it’s not on top of your mind every single day but how you manage your hair already tells people a great deal about you without even talking. With men, one particular haircut keeps coming back no matter what: the undercut. And in recent times, there have been two different styles that look like they are competing with each other—for instance, the side swept undercut and the classic undercut were just two versions of the same undercut concept.
The problem is quite simple: which one serves you best?
This is not about being just another trend follower. It mostly deals with understanding what combination of hair type, face shape, and mood would be appropriate for you. So, let’s get started.
What is a Side Swept Undercut?
The side swept undercut is the combination of two concepts. Sides that are short and clipped off that give an element of contrast. As well as these are the longer top hair that is lying or styled to one side. One more feature is that it is not as defined as the slick back or pompadour undercut. It is not that sharp, it is softer, more casual and sometimes a little disheveled.
- If the length of the hair is medium it works very well.
- While applying some wax, clay, or even if the hair is left undone, it works.
- It also does not lose much of its charm and can be seen as both office and weekend-friendly.
Men, in general, are drawn to styles that strike the right balance—neither too much nor too little. A clean undercut on the sides with some freedom left on top is often the go-to.
For more ideas on finding the perfect balance, explore these hairstyles for diamond face shape male that complement different features.

Classic Undercut: Why It’s Still Hanging Around
A classic undercut is just the opposite of complicated. Jutting or clipping the sides and back, and leaving the top pretty much longer. The top is rather combed back or straight upward if not swept sideways. One can relate this either to the military neatness or the old barber shop style.
This one is more defined, possessing a greater degree of structure. The use of this haircut is optimal when it is required to have a published, and more or less disciplined, appearance.

Comparing Side Swept Undercut vs Classic Undercut
Feature | Side Swept Undercut | Classic Undercut |
---|---|---|
Styling | Relaxed, side-swept, can be messy | Slick, combed back, polished |
Vibe | Casual, modern, approachable | Structured, formal, retro |
Hair Length | Medium to long top | Short to medium top |
Maintenance | Low to medium | Medium to high |
Best For | Men who like versatility | Men who want a sharp, clean profile |
Side Swept Undercut Male Styles That Work
The side-swept hairstyle is more appealing when broken down and explained in actual practical ways.
Messy Side Swept Undercut
It works well if you don’t want the appearance that you put too much effort into it. Rambling a bit, with a few threads laying nicely. Easy-going weekends, dates, or the 30 and under crowd who might dislike the idea of rigidity in style are the kind of clients this hairstyle is perfect for.

Medium Side Swept Undercut
Apart from the medium length, you get the benefit of the multi-aesthetic use. The freshly combed look transforms your style into a more corporate one, whereas the ruffled effect makes you ready for a party. Also, it does not matter if your hair is straight or wavy as it is both doable.

Short Side Swept Undercut
In case of thick hair, short sides and short top with side sweep would probably be the easiest way to keep it at bay. You only need a little bit of product, it is very easy to wash and dries in no time.

Long Side Swept Undercut
More eye-catching. Requires upkeep and the proper hair density. You brush it over, sometimes it is behind the ear, sometimes you just let it lay there. More of a rocker style, but it takes more effort to control.

Side Part Undercut and Variations
This partially coincides with the side-swept but differs a bit. A prominent side part line is what makes the hair cut stand out.
- Men’s side part undercut: Clean, sharp separation, office-friendly.
- Side parted undercut hairstyle: Fade is most common for this style to make the contrast more apparent.
- Medium length undercut side part: You are free to let the hair fall more naturally only with minimal control.

Undercut Side Swept Back View
Most guys only picture the front-on view. But the back view is also important. If the fade isn’t clean, or if the transition is uneven, the style is no good.
A tapered undercut with a medium top that is swept back is one of the best because it makes the back view less heavy without looking blocky.

Side Swept Haircut for Boys and Teenagers
Not only men in their 20s or 30s, but boys and teens can also rock these styles by going for shorter and lighter versions. A medium swept cut works perfectly for straight hair, while a textured sweep looks great on wavy hair. Check out these trendy teen boy haircuts 2025 for more inspiration.

Styling Products and Maintenance
- Used clay or paste to get a matte, textured look.
- If you want more shine and closeness to the classic undercut style, use pomade.
- Use sea salt spray if you want your hair to look like a naturally messy sweep.
- Trim every 3-4 weeks to keep the undercut looking sharp and tight.
Conclusion
Both of them are good. The classic undercut is more pointed, and a bit more suitable for formal occasions. The side-swept undercut is still nice and neat, but more casual, and probably just a little easier to live with day to day.
If you are inclined to either of them, the thing is not to pick one only and stay with it all the time. Hair grows, people’s mood change and so with fashion. Wear one, live with it, then change it whenever you want.
FAQs
1. Is a side-swept undercut suitable for round faces?
Yes, the side part and sweep angles add definition, making the face appear longer and more oval.
2. Can you do a side-swept undercut with short hair?
Yes, of course. There are also side-swept short undercut styles that are suitable for men who like to keep their hair low maintenance, and easy.
3. How do you style a messy side-swept undercut?
Take some matte clay or use a spray, apply it with your fingers, slightly push the hair sideways, and don’t overdo it.
4. What is the difference between a side part undercut and a side swept undercut?
Side part is more formal and neat with a clearly separated parting line. Side swept is less structured, sometimes without a clear part.
5. How often should you trim an undercut side?
If you want to be able to maintain it at its best, then every 3–4 weeks would be the right time to make a new cut.

Roy Anderson brings a deep love for hair care and styling products, offering practical advice on keeping your hair in top shape every day. He reviews popular and underrated hair products to guide readers toward the best choices. Roy also shares home care routines to promote strong, healthy hair.