When it comes to putting that crowning touch on any outfit, whether you’re heading out to a friendly lunch or a cocktail party, nothing compares to a well chosen hat. Unlike other accessories that may subtly change the tone or appeal of an ensemble, even casual hats make bold statements that convey your personal style with the least amount of effort.

But with so many different types of hats to choose from, where do you start? We’ve compiled this simple guide to some of the most accessible and fashionable hats for women, with tips on how to pair the right hat to the right outfit. While hats may have once been associated with bad hair days, these high-fashion headpieces are ready for the spotlight.

For Easy Transitions from Day to Night, Go Cloche!

The cloche (which is the French word for “bell”) was originally popular in the 1920s but its signature bell shape and versatile nature makes it perfect for a day or night look. Since cloches fit fairly snug to the head and don’t have wide brims, they are perfect for indoor and outdoor events.

There are also hundreds of varieties of cloche hats in every color and fabric. Popular trims such as ribbons, feathers, jewels, and fabric flowers can help you achieve a signature look while easily dressing up a simple outfit. These hats are lovely and romantic with a skirt or dress, but don’t let that limit your options! Pairing a cloche with a fabulous jacket and jeans is another great way to incorporate this fantastic hat into your wardrobe.

While many cloche hats can add a vintage flair to an ensemble, a lot of modern day hatters have made the cloche fresh and new. Since the cloche is easy to wear, it’s not a very difficult style to find, even at less expensive stores like Target or Forever21. If you want a cloche that’s a little more original, you can locate independent milliners on sites like Etsy, or peruse auction sites like eBay for a vintage cloche to call your own.

Put some Prep in Your Step with a Schoolboy Cap

For those who enjoy a preppy look, a schoolboy cap may get you an A+ in fashion. These cute hats feature a short, curved brim and are a modified form of — you guessed it — hats that English school boys wore. They are also known as a Baker Boy cap in certain circles. Legendary hat makers the Goorin Brothers make simple and stunning schoolboy caps you can find for under $50 on sites like hatsinthebelfry.com and Amazon.

These hats are historically tied to school uniforms so they pair perfectly with preppy looks featuring vests, ties, plaids and blazers. Schoolboy caps are also commonly made from wool, felt, or fleece, which makes them perfect for fall and winter wear.

Go Boho in a Slouched Beanie

While beanies have always been popular winter hats for practical reasons, recent trends favor a more relaxed, slouched beanie instead of the classic fitted variety. Slouched beanies have come into fashion along with the bohemian look, but you can find a huge assortment of these fun and easy hats in bright knits and even adorned with sequins to add a little glam to your outfit.

Slouched beanies are great because with all the colors and textures available, you can dress up an outfit or simply finish off a casual day look. These hats look great on practically every hair length and texture, and they are incredibly accessible. You can find slouched beanies at most department stores, discount retailers like Marshalls or Ross, as well as trendier stores like Urban Outfitters for under $30 (often times less).

Slouched beanies are great for casual wear and look fantastic even when paired with an outfit as simple as great jeans and T-shirt. Going boho with a 70’s style flowy dress or a layered look with strands of beaded necklaces and some oversized sunglasses is a great option too.

For Sophisticated Elegance with a Fun Twist Think Cocktail (hats that is)

Cocktail hats have made a huge resurgence over the past year. From pill box hats with jeweled embellishments to round, fitted hats with veils and feathers, cocktail hats are the perfect punctuation point for any special occasion outfit.

Unlike larger hats meant to cover all or most the head, cocktail hats are typically small and are worn towards the front of the head and/or slightly to one side. More so than almost any other type of hat, cocktail hats are amazingly diverse in shape, size, texture, and fabric, which makes them the perfect accessory to flaunt your personal style.

Since cocktail hats are typically too small to stay on your head by themselves (especially if it’s windy), most will include a fastener like a built-in comb, bobby pin or barrette, or you’ll need to provide your own.

While you may be able to get away with wearing a rather simple pill box with some of your daywear, they are called cocktail hats for a reason! Use little pieces of art to accessorize a beautiful dress or other types of semi-formal and formal wear for an instant touch of sophistication straight out of the 1940s.

When Picking Out Hats, Remember: It’s All About You

Choosing the perfect hat means choosing the right hat for your style, hair, and outfit. Finding hats that flatter you face, hairstyle, and outfit are easier to find than you think, but it requires some work and a good editorial eye. If a hat just doesn’t work, don’t force it. Remember, you are wearing the hat, not the hat wearing you. But if you stick to some of the fun and fantastic hats in this article, you can narrow your search and find a great hat that is stylish, affordable, and fantastically YOU.