A Guide to the Most Stylish Hats for Ladies

Though I am most well known for wearing large, often elaborate headbands and hair bows, I have also begun to collect and wear fashionable hats. As I began acquiring various specimens to flaunt atop my vacant noggin I learned a great deal about hats, and have come to realize just how much potential women's hats have!

While hat-wearing amidst modern women has become something of a lost art, fascinating headwear is making a comeback, so if you know what's good for you, you'll brush up on your hat know-how! Below I'll guide you through the most stylish hats for ladies one could possibly hope to find. You'll discover there is much more to the world of headpieces than knit toppers and baseball caps.

My absolute favorite type of headpiece is the fascinator. Fascinators are very small hats or clip and/or comb-supported headpieces that do not quite sit atop one's head but rather saunter off to the side. Most fascinators are adorned with interesting feathers, lace, or netting.

Most fascinators are teensy - more like elaborate hair clips than hats, however there is a class of fascinators known as substantial fascinators which is known for slightly larger sizes.  Substantial fascinators can be worn to some more formal occasions in place of a larger, more traditional hat.

One lovely aspect of fascinators is that someone without advanced millinery skills can make one. Because they are fairly easy to produce, fascinators have also been made by many crafters on Etsy, and can be found pretty much everywhere for quite reasonable prices - you might even find some at brick-and-mortar stores like Forever 21 and H&M. Icing by Clare's also sells fun and interesting fascinators, and I have purchased the bulk of the fascinators I own there- mostly because they go for under $20 a piece.

Very similar to fascinators are cocktail hats - in fact, the two styles are frequently referred to interchangeably.

Cocktail hats are distinctly known for being fascinators intended for evening wear, and many include features such as veils, feathers, beadwork, ribbons, and lace.

Of all the hats I own, most are fascinators and cocktail hats - they are easy to put on, can be worn with fancy hairdos or simple ponytails (or even with hair just loose and parted), and are usually inexpensive.

Though we typically think of tophats as male-oriented head adornments, they look FAR better on women- at least in my humble opinion.

While ol' Abe Lincoln kept business papers in his tophat and let the darn thing get pretty mangey (you can have a look at it at the Smithsonian museum of American History), lovely ladies such as Audrey Hepburn adorn (slightly smaller) tophats with ribbons and veils, making the hats (and themselves) look absolutely charming.

Many women used to wear veiled tophats as part of basic riding dress. Tophats do look wonderfully fetching with accessories and can really make one pop out in a crowd.

If you're interested in wearing a femmy tophat, opt for smaller sizes - they should either fit snugly and high or actually perch atop your head. If you want to buy a proper hat, make sure try it on in person and make sure that it fits properly. If you are instead interested in purchasing a tophat that sits atop your head, either go with a version that has combs or clips built in, or one that is attached to a headband. Small, perch-style tophats that are only affixed with an elastic never seem to stay on.

I can and will never see a pillbox hat without getting Bob Dylan's "Leopard-Skin Pillbox-Hat" in my head.  What a great song it is- and it does a great job of portraying the sort of attitude that these interestingly-shaped head-toppers can bring to the table.

Though I've always thought of pillbox hats as exclusively female adornments, the style actually has military roots (picture that type of headgear that was typically seen with a chinstrap).  Interestingly, pillbox-shaped military hats can be traced as far back as the Roman empire!  Back then, it was known as the "Pannonian cap."  Fascinating, no?

It comes as no wonder that some truly powerful women came to wear these headpieces - obviously Jacqueline Kennedy was known for her 'signature pillbox hats' designed by Oleg Cassini, and without a doubt, the woman addressed in Dylan's song is a real heck of a gal.  

I have therefore come to see pillbox hats as real power pieces.  Because they have a more vintage connotation these days (they had their most recent heyday in the '60s), the best place to find pillbox hats is at flea markets and in antiques shops and thrift stores, however you can also buy them new online (think Amazon and Etsy) and get them at normal hat stores. 

For a nice stroll on a sunny day, nothing beats a good wide-brimmed hat. They look great with big sunglasses, and even better with a flowing ribbon tied around the center.

These hats can be as elaborate or as simple as one would choose- it all depends on the material and accessories one goes with - so this is a really wide-open playing field.

While I do not own many wide-brimmed hats (I prefer hats that can be worn indoors since that's where I spend most of my time), I have found that the best places to find them are on Etsy, sometimes through Amazon, and most often through individually owned hat shops where the proprietors make them themselves.

Though they're typically just wide-brimmed fashion hats, I feel the need to point out hats worn to the Kentucky Derby (not to be confused with derby hats, which are also known as bowler hats) are some of the most stylish hats worn today.

The history of wearing showy hats to horse races is certainly long and steeped with intrigue, one-upmanship, and a whole lot of lace, feathers, ribbon, straw, silk, and netting. I hope that the tradition of wearing elaborate hats to such events continues forever.

If you are going to go to the Kentucky Derby (or any other fancy horse race), I recommend really shelling out for a handmade, original piece. The hats worn at high-end horse races are more than just head adornments - they're status symbols. Hence anything less than a rather high-end, handmade, original, and gorgeous hat would be downright embarrassing.

That said, not all of us are going to these races in person, and there are plenty great outdoor hats that you can fancy up on your own if you want to have a little Kentucky Derby party at home!

Some of the best wide-brimmed hats are straw hats, and it's also great to see how dressed up or dressed down these can be. I'm really enamored by old paintings of stateley women going about with beautiful, broad straw hats adorned with colorful ribbons and fresh flowers. Is there anything more romantic?

Of course, straw hats have very practical applications - they make for excellent cool sun protection - so one doesn't even have to be out for style when choosing one.

That said, not all straw hats are wide-brimmed and designed for producing shade. Some of the more popular straw hats these days are smaller, almost fedora-like toppers. They have cropped up intermittently as summer hipster must-haves in various urban communities of young people. So it goes.

Since straw hats are so ubiquitous and inexpensive, you won't have trouble finding them, however if you're looking for something interesting and unique, I recommend getting one that is hand-made.  The best place to buy one-of-a-kind handmade hats online is Etsy, and the best place to buy them offline is in actual hat stores run by milliners.

I hope this guide has inspired you to spice up your collection of head adornments. Hats have a brilliant, fascinating history and it is a shame that more women do not wear them today - they are surprisingly inexpensive ways to spice up one's wardrobe and stand out in a crowd.

If you are just getting started in the world of hats, I recommend browsing through a couple of thrift stores or poking around Etsy online. Both are great starting points, and chances are you'll become both a hat collector and expert in no time!