Ask Brian: Are Hats on Women Hot?

Have you ever wanted to know what guys think about women’s clothing?  Brian gives his expert opinion and answers your most burning questions!


As women, we think that men in hats are extremely hot, especially baseball caps.  Do guys necessarily find it attractive when women wear hats?


Hats are the ultimate accessory; they have different shapes, colors, and fabrics. For guys it’s a little simpler; just wear something that keeps the rain off, or that hides the receding hairline. For ladies however, and how us guys view them, hats are startlingly complex. Guys see a lady’s hat as the cover page to her entire ensemble. The rest of her clothes define what we see, but the hat references it all, and binds it into a single statement. Wearing a hat at all is a careful choice in itself and the lady should always live up to the expectations of the statement the hat is making.

If you’re intention is to fit in with your man (or want to be seen fitting in by other men) in a casual situation, you’ll usually wear jeans, tennis shoes, and probably a patterned T-Shirt. A baseball cap however, not only actually outlines your dress as casual, but defines your intentions as sporty or outgoing. Likewise, a cowgirl hat would be just as appropriate with the same clothes for a woman who wanted to define herself as being wholesome or natural (or not easily tamed).

Semi-formal or business situations require a subtler choice of headgear. As with the rest of your wardrobe, your hat should be more professional and purposefully designed. In no way should this be interpreted as meaning ‘muted.’ Guys admire confidence in the workplace and a lady’s professional hat should define her experience and professionalism. Lady’s business hats are exceedingly rare in the 2010’s, but if you need an idea, review the hats of the 30’s and 40’s. While the hats themselves are dated, it’s clear the relative style is one of demure subtlety.

Formal situations are by far the greatest opportunity for a lady to choose from the widest possible range of hats. From the basic to the exotic, there is no wrong hat to wear. In the formal arena, it’s simply a question of clashing styles. As long as the hat is in a style which complements the rest of the ensemble, that hat is making your statement loud and clear.

More important than what hat to wear when heading out the door, is whether to wear one at all. This can be a more complex question than at first might appear. To put another way: guys are a mass of complex emotion and triggering the right one takes careful planning. We like to see everything ‘make sense.’ We like to see long hair flowing from a baseball cap or cowgirl hat, but wouldn’t want to see that from a business or formal hat. The latter would convey a confused statement: your cover page is saying that you are a serious professional, but your resume is only telling us what you like to do for fun. 

So if your choice of hats and your preferred hairstyle seem to contradict each other, they probably do and you may consider leaving the hat at home.

Finally, as you would want your resume to exemplify your cover page, you should always live up to the expectations generated by your hat. Guys do not like being lied to and that is also with respect to what they see. For example, if a woman walks into a western bar with a cowgirl hat, half-tee, tight jeans, and boots. I’m expecting her to be down-to-earth, fun, and good-natured. But if she starts talking about the political climate in India or the infuriating memo she got from Doug in Accounting, then my perception is shattered. Wearing a hat is not the same as wearing a watch; it is an accessory you have to live up to, demonstrate, explain, and (sometimes) apologize for.

Guys enjoy looking at women, and the more we see, the more pleasant the distraction. But we don’t what to simply see what you look like, but who you are. We want to know what your purpose is and what that means to us. And the longer it takes for us to figure that out, the more likely we will lose interest, and start looking at the woman sitting next to you. So when you are organizing the resume of your fashion, make sure your hats are providing you with a workable mission statement.

~ Brian E. Shefveland, Associate Editor


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