“That’s my Mama’s vacation hat,” my 7-year-old daughter explained to her friend pointing to my cream straw fedora. “She only wears it when we’re going away.”

It was sitting out in the kitchen instead of tucked away on my closet shelf because we had in fact just gotten back from vacation. I never thought I’d have an item of clothing that really only came out on jaunts away with the family (What am I 90? Next I’m going to have a vacation mumu), but children…they speak the truth.

There are certain types of clothing that make me feel inherently…fussy. Hats (not winter hats that are functional, but warm-weather hats), maxi dresses,  to name a couple. They just draw attention. They make the person who is wearing them look like they are trying. Even those adorable fashion bloggers. Yes even them. I see one wearing a cute hat with a little maxidress, scarf, heels and I think to myself, “Really? You would walk down the street in real life wearing  all that stuff? And then the hat on top of it? ” And I’m a stylist. I do this for a living. I follow trends, what’s hot and what’s not. But a hat. It can easily, easily, easily scream “Hey there everyone! Check out ME hat. This one! On my head!!” And that’s the last thing you want  — or at least it’s the last thing I want.  With myself and my clients, I strive to create looks that are chic/cute and comfortable/effortless. Because that is the key to true style. It looks like you aren’t trying.

So, back to my vacation hat. Why do I then don a hat on vacation? When I get ready to travel during the summer, 9 times out of 10 I am wearing a a comfy t-shirt, khaki shorts and flat sandals. Accessory-wise, minimal (I have three young children, if you get my drift). Maybe my menswear-inspired watch, stud earrings and that’s it. Simple, comfortable.

But, I still gotta feel like I’m having fun, right? Hence the hat.

So, if you’re going to rock some sort of cute hat — like a bowler, fedora, cowboy or otherwise, my suggestion is this:

1. Keep the rest of the outfit simple… jewelry around neck and ears minimal

2. Nix any scarves — too much going on above the neckline can overwhelm.

3.  Opt for non-sexy shoewear.  You want it to be like “Hey, I just threw this hat on,” and stilettos don’t say “Hey, I just threw this hat on.”  My favorite look with a hat is a summer dress, flat sandals and a straw fedora. Bam. If you want a great example of another casual way to do a hat, Sydney of The Daybook gets it right…right here and here.

So there you go. My thoughts on hats. Oh, and here I am with my hat (and a kid in the backseat).  The rest of my oufit? Graphic T-shirt (Bethesda Crab House, I think?), khaki shorts and flat sandals, natch.