“Once I read a story about a butterfly in the subway, and today, I saw one. It got on at 42nd, and off at 59th, where, I assume it was going to Bloomingdales to buy a hat that will turn out to be a mistake – as almost all hats are.” -Kathleen Kelly, from “You’ve Got Mail”

As a former hatter in a tack store, and fan of headwear in general, I strongly disagree, I love a great hat! We’re headed into Triple Crown, Polo, and summer wedding season, and you don’t have to be of noble birth, or even a guest in the Royals’ box at Ascot to wear them. Thanks to Duchess Catherine, hats and fascinators (among women in particular) have grown in popularity again, and American women have embraced the trend. Despite my invitation having been lost to Catherine and Will’s wedding, I still dressed the part and went in to the office that day…


It’s all in the details. Wearing a hat is a commitment. Before launching yourself into the upper echelon of style, be aware of the number of considerations to be made, based on season and event. Hats have seasons, and just like reserving your white attire for Memorial Day through Labor Day, that’s the only appropriate season for straw hats. I know country music artists break that rule all the time, but please don’t assume that because they do it, it’s okay. Labor Day through Memorial Day you should be wearing something in felt or wool, regardless of the odd warm, sunny day. However, a felt or wool hat can be worn year-round. Follow the rules, you won’t look a fool!

For men, it’s a bit simpler. For day wear, you have a few selections, and the two most common tend to be the fedora and the newsboy. Of the two, the fedora is considered more formal, but both can be dressed up or down to suit. With all due respect Pharrell, the deranged Canadian Mountie look isn’t a good one for you or anybody, please stop. Other than knowing which material is suited for the time of year, your etiquette guidelines are fairly simple, thanks to hats.com:

Men Can Leave Hats On When

  • They are outside
  • At an athletic event, indoors or out
  • In public buildings like post offices, airports, or hotels
  • On public transportation
  • In elevators

Men Should Take Off Hats When

  • They are sitting down to eat a meal
  • In a house of worship unless required by religion
  • Public buildings like schools, town halls, and libraries
  • When the National Anthem is playing
  • In restaurants and cafes

men 1 Monsieur Jerome

For the ladies, as in most things, our hats are often more complicated as are the rules that accompany them. There aren’t as many hard and fast rules, apart from knowing what’s in season, more rules of common sense (hopefully common).

My first rule is fit. I happen to have a smaller head, which can make finding a hat to fit, or fitting a “one size fits most” hat a challenge. You need to understand how your hat of choice is to be worn, and ladies please, the answer is almost never with giant bangs, tipped way back off your head. Generally a hat will sit just above your brow, above the ears, and around the widest part of your head. It needs to fit securely enough to stay put in a gentle breeze (pay attention to the weather if you’re “hatting” outdoors, the big ones can be quite unwieldy), without giving you a migraine. If you can afford a custom fit, congratulations, but for the rest of us, here’s my handy cheat, foam insulation tape that you buy at the hardware store. It has adhesive on one side, so when you decide where you need it, it will stay in place, and so will your hat, and the foam allows you to create a snugger fit, without smushing your hair (or brains). Cut 4” strips and place them between the fabric band on the inside and the hat itself in different places until your hat feels secure, then use the adhesive to secure the padding. You don’t have to use the adhesive, especially if you’re only planning to wear it for a short time, then sell it. It will still work, but the foam can shift.

My second rule is vision impairment. A big floppy brimmed hat can be beautiful and dramatic, except when it blocks your vision and you bump into things. I have a simple straw style for summer, which makes me crazy when I’m talking to someone, or trying to see where I’m going, because it tends to block one eye. The positive side of it is that it blocks the sun from my face, neck, and a bit of my shoulders, so I like it for when we go boating or to car shows. As much as I enjoy a bronze summer glow, I love my skin more, and would prefer to not look like an old handbag as I age!

hot rod

My third rule is environmental awareness. No, your hat doesn’t need to be made of recycled materials, but you do need to know the impact of a large hat, or one with pointy feathers/decorations can have on a crowd of people. Is the hat you’re considering so large in height or width that it might block someone’s view from behind you? If you turn too quickly, is there a risk of stabbing? For large, possibly close-packed crows, I like a fascinator. They can still be elaborate and glamorous, without taking up a lot of space, or creating visual barriers for you or those around you. They also lend themselves more to photo ops. Lastly consider your form of transportation. They can be a real nuisance getting in and out of cars, so make sure it either fits easily, or can be removed and replaced with minimal effort.

royals box at ascot

My fourth rule is practice. Wearing a hat for the first time is no different than wearing your first pair of heels, it takes practice. Trying it on and taking selfies for a few minutes is one thing, but wearing a hat, especially a large one all day can really wear you out. As silly as it sounds, wearing it for a few hours at a time at home, can make your big hat debut more bearable in the long run, plus it will help you figure out a suitable hairstyle, and whether or not you might need a little extra padding in the band.

Lastly, suitability. Your headpiece should complement your outfit and you, not the other way around. If it feels like the hat you’ve selected is wearing you, it might be wise to scale back a bit. Your hat is an accessory, and the absolute best accessory to go with it, is a smile. If you’re grimacing or uncomfortable looking in it, then the whole outfit is a loss. If your outfit has a bold pattern, choose a solid color hat in a similar color with a little detail that compliments the other colors. If you’re wearing something simple, try a hat with a little more detail. It’s all about balance. The same applies with the rest of your accessories, if you’re wearing a fabulous hat, leave the statement necklace and giant earrings in the box that day, keep the rest simple. Hats, above all else, represent elegance and sophistication. Pile on every stitch of jewelry you own with a big hat, and you’ll look like you’re playing dress up.

queen hat

kate in hats

There’s a fine line between ridiculous and sublime, part of wearing a hat, is knowing how to toe that line in style.


red hat


2 thoughts on “HAT TRICKS

  1. I love hats!! I wish I knew the secrets of making them, I’ve made a few fascinators, but only very simple ones. Do you think it’s appropriate to wear a fascinator around, or are they only for formal events?


    • I would say to events in general, yes. I wore mine to a friend’s engagement party at a dance studio and got lots of compliments, (the one I was wearing in the blog) so it wasn’t too over-the top. The key to a hat or fascinator is confidence. If you feel good wearing it, then it will look great, if you’re worried what others might think, it will look silly. Thanks Courtney!

      Liked by 1 person

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