Entertainment Fashion & Style How to Wear Fall's Most Fashionable Hats Share PINTEREST Email Print Fashion & Style Accessories Tops & Sweaters Dresses Skirts Jeans Pants Do It Yourself Shoes Skincare Advice Makeup Hair Fragrance Tattoos and Body Piercings Kids and Teens Bumps & Babies Learn More By Kim "Kimmay" Caldwell Updated on 05/23/19 01 of 09 Rust Colored, Wide Brim Lisa Rosado wears the Luna hat from Worth & Worth. The Style Theory Collective/Laurel Lister Hats are one of the easiest ways to add dimension and color to your Fall wardrobe. Crystal Cave, personal stylist of xo Crystal Cave says, "Styling a hat should be considered as part of your overall outfit. They're also a great opportunity, like a statement necklace, to add a bold personal touch to your look." Want to style your hats, or try something new? Try these tips! When it comes to choosing a hat, Lisa Rosado of The Style Theory Collective has this suggestion: "My biggest tip would be to invest in a hat straight from a millinery. This gives you the opportunity to try a wide assortment of styles and have your perfect topper sized to perfection. There's nothing worse or more fussy than having to run after your hat soaring through the air on windy days. They are also able to shape the hat to your liking or in a way that is most suitable for your face shape, which is pretty neat." Try the Luna Hat in Rust that Lisa is wearing from her favorite milliner, Worth & Worth. Style Tips: Try this rust colored hat with a creamy blazer and cool toned dress.Want to try a notice me look? A large brimmed hat and large sunglasses make a bold statement.Wear your hair down and slightly casual or in looser curls for a put together but not too fussy look. This kind of hat commands attention in a laid back way.Wear a cross body bag in leather, suede, or a softer fabric for an easy but refined look. 02 of 09 Floppy Hat Francesca's This Ione Classic Floppy Hat from Francesca's is only $34, a great price point for trying out a trend. To keep things classic, try a color like burgundy, which is a fall trend that comes back year after year. This floppy hat makes you want to embrace all of the fun outdoor activities fall has to offer from visiting a pumpkin patch to picking apples in an orchard. Not sure if this color is for you? Take this advice from Melanie Kluger, Personal Stylist and Closet Connoisseur of Head Over Heels with Melanie: "Buy a hat that coordinates with your outerwear. Chances are if you have a hat that works with your favorite outer layer you'll be more likely to throw it on to complete your look seamlessly." Style tips: This oversized style can be a bit floppy, so pair is with something form fitting on the bottom.Try this 70's inspired hat with wide leg jeans and a turtleneck for a retro sophistication. Wine and other warm neutrals like camel, khaki, and olive green go great together.Or go for a rich look with a deep navy, dark purple, or classic black.Dress it up with classic riding boots and a trench, or even high heels and a curve hugging sweater dress. 03 of 09 Faux Suede Baseball Cap Torrid For those days when you need to remind yourself of just how powerful and awesome you truly are. The baseball cap style has been making a comeback among the most fashionable for a couple seasons now. Crystal Cave, personal stylist of xo Crystal Cave says: "Baseball hats have been more popular in recent years. Think of using it like a graphic tee with a fun design or phrase." Try an elevated version like this Slay Faux Suede Baseball Hat from Torrid with the modern woman's slogan and intention for the day: “slay.” Style Tips: Pair this updated casual classic with the casual uniform: jeans and a white tee-shirt. Understated, simple, and easy to wear anywhere. Add in your favorite sneakers, or kick it up a notch with boots.Try not to get too matchy-matchy with a suede jacket. Instead, go for denim, canvas, or nylon. Even a simple and stylish sweatshirt can look great with this hat!For a fun look, wear this hat with large gold hoops and a stylish romper or jumpsuit. This hat is especially useful for running errands or catching brunch with girlfriends on Sunday after a night out on the town Saturday. Don't let bedhead or that hangover keep you from slaying the day. 04 of 09 Cashmere Knit Skida When the temperatures start to dip during the Fall, try this Skida Sherburne Knit Hat. Made from 100% cashmere in Nepal, it's quite possibly the coziest thing you'll wear on our head. It's great for outdoor activities like hiking, and because of its classic, no fuss style, it can go with just about anything. Versatility is key for Fall, as the temperatures are always changing. Style Tips: The chunky rib knit goes great with a loose, side braid. No need to be too formal or overdo it with a glam look. Simple makeup like a tinted moisturizer and lip gloss, plus a swipe of mascara is all you'll need for this casual look. Invest in a pair of sturdy hiking boots, a warm jacket, and wool leggings for that outdoor vibe. Pair it with a smart peacoat and high heeled boots for a weekend getaway. If it gets too warm, you can easily stash the hat in your weekend bag, and bring it out for time around a fire pit or a look at the stars. 05 of 09 Vintage and Bold The Feathered Head. Produced, styled and edited by Bard + Paul. Photography by Angela Paul. Vintage and velvet are a great way to express your personal style this Fall. Go bold with a throwback in a vintage hat like the Jessamyn from The Feathered Head. It's pretty much the only thing you'll need to make your outfit sing. Designer and owner, Andie Cohen-Healy adds, "Remember, you’re wearing a green turban as your main accessory so it goes without saying, keep jewelry to a minimum and be confident!" Style Tips: Wear this olive green velvet and golden satin vintage turban with a muted or earth tone blouse in cream, or white.Mix and match vintage, retro, and modern clothing for an eclectic look.The velvet of this hat has a rich texture and is perfect for Fall weather. Try pairing it with other textured fabrics for a lush and lavish outfit. A knit sweater dress, velvet leggings, or boucle vest are all great options to play with.Be fierce! This bold hat is screaming for you to let loose. Try a bold lipstick, sky high heels, a plunging neckline - anything that is outside of your comfort zone. 06 of 09 Classic Beret Brixton/Van de Vort The beret has always been a chic, fashionable hat. This Fall, it's here in a big way. Try one in a bold color, like red, or go for a crisp and clean look in ivory. This Audrey Beret from Brixton, available at Van de Vort online or in the Flower Hill Promenade in California is a perfect addition to your hat wardrobe. Simple, sophisticated, and a little bit whimsical. Ooh la la! Style Tips: Wear your beret slightly forward on the head and tilted to the side for the Parisian look. Or, wear it back on the head and flatter for a youthful, sweet look. Give this classic hat a vibrant boost with a flowing crop top and matching pants, gold hoop earrings, and a dazzling floral vest with bright pops of color. Stay simple and chic with this hat and a basic black shift dress and pumps for a classy outfit, or jaunting between business meetings. A classic hat calls for classic makeup. Try a simple cat eye liner in black and a truly red lip for that old school look. 07 of 09 Navy and Tassels Lockwood Style, Shiraleah A dark blue or navy color is a Fall must have, especially when it comes to a hat. But there's no need to keep it boring. Try a navy hat with a little punch to it, like an on trend addition, such as tassels. Maria Chavez, the Women's Buyer at Lockwood Style in Astoria, NY, mentions: "Tassels were the big statement piece all spring and summer and it's not going anywhere! We are still going to see them all fall and winter. Hats with tassel trims make it a fun way to add this trend to your look" This Posh Hat by Shiraleah, available at Lockwood Style in NYC, is the perfect blend of funky, and fashionable. Style Tips: Pair this dark hat with light color clothing, such as a pair of light denim jeans. Don't be afraid to mix black and blue! The color combination is not only sophisticated, it's also a great way to mix up a monochromatic outfit with small variations in color. Use this hat to top a basic outfit for a special punch of whimsey, and fashion forward fun.This hat looks great with trench coat - try one in a burnt orange, deep olive, or mustard yellow. 08 of 09 Olive and Wide Brimmed Tobi Wide brimmed hats are great for adding volume and interest to your Fall outfit. In fact, Maria Chavez, Women's Buyer at Lockwood Style, says: "Structured wide brim hats allow you to compliment and create effortless shapes with your outfit. Have fun matching your hats not only to your clothes but also to other accessories. Think of adding a matching silk neckerchief or matching mirror sunglasses." This Million Reasons Olive Hat from Tobi is a great option. The color is just neutral enough to wear with most Fall outfits, and just interesting enough to add some pizazz to your wardrobe. Style Tips: Think of mixing a structured hat with a more flowing outfit, like this off the shoulder top, for more of a bohemian style. The warm color of this olive hat makes it great for wearing with leather pieces like bags, jackets, or boots in warm brown tones like cognac. Leaving your hair down, or wearing it in one or two braids looks top notch with this style. Keep makeup neutral with a skin tone lipstick, a little bronzer, and a smokey brown eyeliner. 09 of 09 Classic Black Rosa Delgado/Melanie Kluger Want to keep things basic? Melanie Kluger, Personal Stylist and Closet Connoisseur of Head Over Heels with Melanie, has this advice: "Choose a hat that has versatility. While we all want to wear the most vibrant color in the bunch, if your hat collection is small, start with a neutral navy or dusty gray before graduating to a bolder hue." And you can't go wrong with a great black, classic hat. Style Tips: Go for an all black look, coordinating your hat with the rest of your outfit, then pop on a plaid scarf for a pop of color. Black can easily be dressed up, so consider wearing this with a stylish wool coat or dark, leather moto jacket. Either way, you'll look your best! Match your hat to your belt and bag when you want a polished, clean look. Wear this with a 1970s style pantsuit in a vibrant color like wine or dark green for a throwback look.