The arrival of a new season is the *perfect* opportunity to debut a brand spankin’ new look. You never know: Trends you may have deemed outside of your comfort zone in the past could suddenly be way less intimidating this go around (or perhaps you’ve just become more of a risk taker). Now that you know how to style your scarves and how to rock socks, there’s no time like right now to take your hat game to the next level. None of this nonsense about not being able to pull off a hat — it may take a little trial and error, but you best believe that when the hat fits, you’ll never want to take it off. Between floppy wool styles, berets and felt fedoras — just to name a few of the season’s most enviable styles — we’ve put together 13 foolproof #HOTD (hat of the day) pairings to ensure you don’t miss a beat when it comes to maximizing your hat collection this fall. You’re so welcome.
HOW TO STYLE A RIBBED HAT
1. J.Crew Ribbed Cashmere Hat ($68) + Scotch & Soda Lurex Jacquard Pullover ($198): Turn down the chance to inject some major color play into your predictable wardrobe of neutrals? Not this girl. The first sign of 30-degree temps will have you reaching for this soft — and oh-so-very luxurious — ribbed cashmere hat in a punchy emerald hue. Round out your cold-weather look with a retro mohair sweater, leather pants and desert boots for anything from your alma mater’s homecoming weekend to a last-minute getaway to the windy city. A faux fur hooded parka may be required.
HOW TO STYLE A CHEEKY BEENIE
2. Kate Spade Winking Beanie ($58) + Scotch & Soda Tartan Shirt Dress ($135): Baby, it’s cold outside — and we haven’t seen nothin’ yet! It’s not too early to start shopping for the perfect beanie that protects you from the elements in style. Kate Spade nailed it with their playful winking beanie that will elicit smiles from random passersby and maybe even catch the eye of your Tinder crush. For a comfy-cozy log cabin vibe, slip this cheeky knit hat on with a tartan shirt dress, marled socks and duck boots. All that’s missing is a cuppa hot chocolate and an extra snug shearling coat.
HOW TO STYLE A FUR BEENIE
3. Topshop Fur Beanie Hat ($40) + Mango Cotton Wool-Blend Coat ($130): Don’t back down now: If there’s anything we’ve learned from The Devil Wears Prada, it’s that you need a cerulean topper in your life STAT. Throw in a faux fur leopard print beanie (all the more to keep your forehead nice and snug) for a rawr-tastic accent that won’t go unnoticed once the first polar vortex hits. Keep things on the DL with sleek leather leggings, a cream-colored fisherman sweater and Chelsea boots for a stint downtown.
HOW TO STYLE A SATIN BASEBALL CAP
4. H&M Satin Cap ($13) + Ban.do x Stickybaby Good Vibes Bomber Jacket ($180): You boss babe, you! Someone with your level of natural swagger and fierceness can 100 percent pull off a fly satin baseball cap with this much panache. Less tomboy-chic, more man-repelling, this sporty hat is just waiting to be teamed with a vintage bomber jacket, rolled-up boyfriend jeans and some well-loved Chuck Taylors for an athleisure look. Street MVP status won’t be too far behind, if you have anything to say about it.
HOW TO STYLE A POM-POM CAP
5. Kate Spade Felt Cap With Marabou Poms ($98) + Zara Sweatshirt and Skirt Dress ($50): When sporty meets playful, this black marabou Mickey Mouse-esque pom-pom hat will make you feel like the ultimate #girlboss — and for good reason. It’s not every day you see a stylish lady about town parading around in a hat with this much look-at-me appeal. For a getup that’s glam AF, throw this off-duty-meets-after-hours sweatshirt dress featuring a pleated metallic hem into the mix alongside some Adidas Superstars for ALL the style points this season.
HOW TO STYLE A WOOL TRILBY HAT
6. Ted Baker TYLI Wool Trilby Hat ($85) + Zara Patch Coat ($229): For an outfit that’s easy like Sunday morning, don’t hesitate to invest in this charming trilby hat that’s guaranteed to make your morning commute infinitely more stylish. Not only will the color-block design pair well with everything in your wardrobe, but this hero piece takes zero effort (seriously, nada!) to style. Throw in an entrance-making coat covered in rad patches for a nine-to-five uniform that demands attention. Sign us up, please.
HOW TO STYLE A WOOL-BLEND BERET
7. H&M Wool-Blend Beret ($13) + Free People Velvet Lengths Maxi Slip ($128): Your excuse to dress like a French girl has arrived in the form of a very chic wool-blend beret. *Adds to cart without hesitation.* Instead of whipping out the Breton stripes and effortless ballerinas, take it there with an after hours-approved velvet slip dress that’s anything but blasé. Be it a Gatsby-inspired fall soiree or a GNO, the result will be très chic — especially when teamed with a studded leather moto jacket and tough-girl combat boots.
HOW TO STYLE A WIDE-BRIMMED HAT
8. J.Crew Wide-Brimmed Italian Wool-Felt Hat ($75) + Zara Cropped Layered Jumpsuit ($70): Nothing to wear for so-and-so networking event or an upcoming dinner party? Think again. Come autumn, there’s something to be said about a slew of rich jewel tones that exude holiday dazzle (even if you’re just hosting a little get-together). Meet the cabernet-hued Italian wool-felt hat you’ll find yourself reaching for time and time again this season — everything from a road trip out west to a late fall wedding in the countryside. Armed with a gorgeous teal jumpsuit and some high-heeled ankle boots in tow, the result will be nothing short of groundbreaking.
HOW TO STYLE AN ANIMAL-SHAPED BEENIE
9. Forever 21 Fox Face Beanie ($10) + Zara Front Buttoned Pinafore Dress ($50): Does this cheeky fox face knit beanie not make you want to go jump in a gigantic pile of leaves or take a trip to the pumpkin patch? That’s not even a question. When adulting is not what it’s all cracked up to be, channel your recess days with a grown-up denim pinafore dress, a wooly knit sweater and a set of fox ears, for a look that says, “You got it, dude!”
HOW TO STYLE A BOWLER HAT
10. & Other Stories Wool Bowler Hat ($75) + Madewell Silk Ruffle-Hem Dress in Windowpane ($168): Get ready to swoon hard for this #winning combo that will never steer you wrong. Between peaceful walks in Central Park and an outdoor picnic on a seasonably warm fall day, a wool bowler hat is practically obligatory. Don’t even get us started about that charming bow detail. Pair with an ultra-feminine frock — this silk windowpane stunner featuring a ruffled hem is actually perfection — and throwback suede Mary Janes for a look that’s autumnal AF.
HOW TO STYLE A CLOCHE HAT
11. Kate Spade Bow Cloche ($88) + Madewell et Sézane Igor Cape ($268): Practically out of an Edward Hopper painting, this ‘20s-inspired cloche is as timeless as it gets for the old soul with modern-day style sensibilities. Channel your inner lady in red with this snazzy bow-topped hat that can double for a fall fête or date night with your boo — just toss it on alongside this classic gray cape featuring a shearling collar and swipe on some red lipstick for a getup that wows. Come after-hours, a drop-waist dress and chunky block heels will make you look (and feel) like a leading lady in an Old Hollywood film.
HOW TO STYLE A COLOR-BLOCKED HAT
12. Scotch & Soda Colour Blocked Hat ($159) + Wilfred Trompette Dress ($135): You know what they say: If the hat fits, wear it! When you find a stylish topper that looks just as ah-mazing with dark-wash flares as a school girl-inspired suede trapeze dress, you know you’ve struck gold. For an Instababe-approved look that works its magic around the clock, toss this elegant wide-brimmed hat (check out that granny-chic bug brooch!) on with a drapey trapeze dress and a pair of the season’s most coveted OTK boots. Take note: THIS is what you reach for when a case of the outfit blahs hits or the next time you press the snooze button one too many times. Let the compliments rack up.
HOW TO STYLE A DELIVERY BOY CAP
13. Wilfred Free Dyberg Hat ($45) + Zara Blazer With Elbow Patches ($129): Introducing the menswear-inspired cap that reads a little bit Jenna Lyons, a lot your neighborhood delivery boy (albeit a very cute one). AKA, it’s more than deserving of a spot in your fall capsule wardrobe. Part ’70s, part utilitarian and part military, this sartorial workhorse calls for pegged trousers, an ochre-colored elbow patch blazer and kicky heeled loafers for an HR-approved look that slays.
What’s your go-to way to style a fall hat? Follow us on Pinterest for more style hacks and colorful outfit inspo!
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