How to Attract Women with the Right Hairstyle and Haircut

Dear Michelle Valentine,

I’m new to the dating scene, and after attending your last event for professional singles, I realized my super-long hair looked out of place with my outfit.

Do you have any hair styling tips for men?

Rocker Dave

Dear Dave,

You’ve asked an excellent question—and one that many men overlook when stepping back into the dating scene. From the very first impression, women are observing everything: clothing, grooming, and yes—your hairstyle. Hair sends a message before you ever speak, and women often use those subtle cues to determine how well a man might fit into their life long-term.

The truth is, hair that’s too long or unkempt can unintentionally send signals of rebellion or irresponsibility. While you may not be either of those things, updating your look can dramatically improve how women perceive you.

What to Avoid with Men’s Hairstyles

Hair that Looks Too Sexy

This is the big, fluffy, flyaway look—like you just stepped off a rock stage. It can come across as trying too hard or as though your priorities are still stuck in your younger years.

Hair that Looks Cheap

Straggly ends, limp texture, or hair that clearly needs several inches trimmed away can make you look careless. Women notice—and it often translates as “he doesn’t take care of himself.”

Hair that is Too Career-Only

The stiff, overly neat “boardroom look” says you’re all business and nothing else. While professional grooming is important, women also want to see personality, approachability, and a little flair.

The Right Look to Attract Women

According to Robert Pante, author of Dressing to Win, a hairstyle should have the right balance of sex, money, and career. This couldn’t be more true. The most attractive look is one that projects richness and prosperity—not in the sense of wealth, but in terms of health, vibrancy, and confidence.

• Shiny, healthy hair – Invest in a good shampoo and conditioner; dull, lifeless hair never makes a strong impression.

• Well-trimmed ends – Regular cuts keep your hair looking deliberate rather than accidental.

• Natural-looking color – If you color, make sure it looks believable and flattering.

A Note on Gray Hair

Many women find natural graying at the temples incredibly distinguished and masculine. It often adds a level of sophistication that dye jobs can’t replicate. Embrace it if it flatters your look—you might be surprised how many women appreciate the confidence.

A Note on Baldness

Here’s a secret: most women prefer a man who owns his baldness over one hiding it. A clean-shaven bald head can be stylish, bold, and attractive. On the other hand, nearly all women dislike thinning hair that’s combed over or an obvious hairpiece. Confidence always trumps cover-ups.

Your Next Steps

The easiest way to find your best hairstyle is to research current men’s fashion and style magazines—both in print and online. Clip or screenshot the looks that appeal to you, and bring them to a skilled hairdresser or barber. A professional can adapt the style to your face shape, hair texture, and lifestyle.

Remember: your hairstyle is an investment in how others perceive you. Updating your look might just be the final touch that helps you make a strong, lasting impression on your next date.