One Boot, Your Rules: How to Style Blundstone #585 Boots

This article was produced in partnership with Blundstone

We love the idea of a capsule wardrobe: You invest in elevated essentials that comprise the fundamentals of an outfit, leaning into classic silhouettes rather than playing into fleeting trends. It makes getting dressed less frenzied whether you’re scrambling in the morning before work or packing for a last-minute trip. That doesn’t mean you forgo your personal style for that of a uniform; you merely streamline and simplify. Let’s start with your shoes. If there’s one pair that really can do it all, it’s Blundstone’s Classic #585 Chelsea boots in Rustic Brown.

They transcend seasons and dress codes, living in a sartorial sweet spot. With Blundstone’s #585, you can skip all that tedious decision making and shoe swapping: This boot is versatile enough to do it all. With its premium supple leather upper, durable outsole, and utilitarian aesthetic, the #585 can handle whatever your day has in store.

“Being a Chelsea boot, it allows the shoe to be dressed up a bit more without feeling too rugged,” says men’s stylist and image consultant Patrick Kenger, “but it still has those functional outdoor sensibilities.”

From top to bottom, Blundstone’s Classic #585 is built to perform and look good doing it. The upper is made from weather-resistant leather in Blundstone’s signature rustic brown, a now-iconic shade that (as you’ll see below) pairs well with all kinds of outfits. Unlike other men’s boots that have to be babied, Blundstone’s Classic #585 offers exceptional durability and only gets better with age: Over time, the leather conforms to the shape of your foot and acquires a patina that lends character. 

Courtesy of Blundstone

Blundstone’s work boot heritage—the brand has been producing reliable footwear since 1870—is evident in a multitude of details. The #585 is constructed with abrasion-resistant thread that can withstand bumps and scrapes, and the boot’s TPU outsole is hardwearing and assists with lockdown traction on city sidewalks and backcountry trails.

A good boot needs to be comfortable, and #585 serves up a cushioned ride that’ll keep your feet happy even when you’re trekking all day. It utilizes Blundstone’s SPS Max Comfort System that absorbs 90 percent of impact and proprietary XRD cushioning at the heel to further diminish impact with each step.

Given its thoughtful construction and eye-catching good looks, it’s no surprise the #585 is Blundstone’s bestselling boot. To get more insight into the model’s versatility, we tapped Kenger to create five looks around the #585. Whether you’re hiking to a summit or heading out for a dinner party, these boots have you covered. 

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1. Casual Date Night

Date nights can be a tough occasion to dress for. You want to look put-together, but you also don’t want to go overboard. Choosing a boot like Blundstone’s #585 grounds your outfit with a dose of timeless style, and it’s an ideal choice for a casual night out: It’s sophisticated without trying too hard.

“I’d shoot to pair the boots with jeans that aren’t too distressed or beat up,” says Kenger. To keep the laid back vibe in a way that’s rugged and refined, Kenger suggests opting for a dressier flannel.

Go all-in on Americana brands à la Faherty and Levi’s for a look that’s timeless. Levi’s 501 Original Fit Jeans and the Faherty flannel are comfortable and effortless.

• Faherty The All Time Shirt in Granite Canyon Plaid [$158; faherty.com]
• Levi’s 501 Original Fit Jeans [$80; levi.com]
• Blundstone Classic #585 Chealsea Boot [$230; blundstone.com]

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Morning Hike and Coffee

Whether you’re in the hills of California, in a Brooklyn borough, or somewhere in between, there’s something to be said about the sacred ritual of the morning coffee walk. Rather than make multiple pit stops to change between getting your steps in and meeting friends for an Americano and a croissant, you can don the Blundstone Classic #585.

The boot combines legendary durability and performance with iconic style. Pair it with the Topo Designs Dirt Pants, cheekily named for their soft and stretchy cotton-spandex fabric that’s suitable for hiking, climbing, and cycling. Kenger recommends topping it off with the Kühl Thor quarter-zip sweater. The poly-merino-nylon fabric offers great temperature regulation and a comfortable feel if you work up a bit of a sweat.

• Kühl Thor ¼ Zip in Gotham [$129; kuhl.com]
• Topo Designs Dirt 5-Pocket Pants in Dark Khaki [$109; topodesigns.com]
• Blundstone Classic #585 Chelsea Boot [$230; blundstone.com]

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Long-Weekend Trip

Got a trip coming up? Don’t settle for tired sweatpants and sneakers on your travel days—or schlep another duffel just for shoes. You need footwear and apparel that keep you comfortable, looking sharp, and go with everything you pack, no matter where you’re headed. This is another scenario where Blundstone’s #585 shines.

“Start with a classic work pant that pairs great with the versatile nature of the boot,” says Kenger. “I like to wear a plain tee for comfort, then pair a lighter jacket on top, mainly for storage and for those colder flights.”

The Camp Pant from Taylor Stitch serves up a modern take on vintage work pants, and Kenger likes the Frank jacket from Mavi Jeans because it has some added stretch for a more accommodating fit.

• Uniqlo U Crew Neck Short-Sleeve T-Shirt in White [$15; uniqlo.com]
• Mavi Jeans Frank Denim Trucker Jacket [$128; nordstrom.com]
• Taylor Stitch the Camp Pant in Stone Boss Duck [$128; taylorstitch.com]
• Blundstone Classic #585 Chelsea Boot [$230; blundstone.com]

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Dressy Evening Event

With their iconic Chelsea boot silhouette, and unique rustic brown colorway, the Blundstone #585 can clean up as well as you do, and they’re a great choice for dressier occasions. Kenger recommends combining them with a darker, undistressed pair of jeans and some classy layers on top.

“I’d go with a nicer tee or sweater from J.Crew,” he says. “Finally, top all that off with a casual blazer that looks at home with jeans and your Blundstones.”

• J.Crew Cotton Piqué-stitch Crewneck Sweater in Heather Carbon [$80; jcrew.com]
• Buck Mason Carry-On Jacket in Canteen [$178; buckmason.com]
• AG Tellis Jeans [$225; agjeans.com]
• Blundstone Classic #585 Chelsea Boot [$230; blundstone.com]

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A Fall Day Spent Outside

Fall is here, and that means it’s time to start prepping your wardrobe for colder weather. However, there’s one thing you won’t have to change: Your shoes. The Blundstone #585 is the ideal footwear option for fall and winter. Its leather upper blocks rain and moisture from soaking your feet, and pairs well with cozy fall garments. For colder weather this fall and winter, opt for thicker pants, a sweater, and a topcoat with your Blundstones.

The Wellen Headlands Sweater offers the chunky design of a classic fisherman’s sweater in a soft, warm cotton-acrylic-polyester fabric, and Kenger points to Charles Tyrwhitt’s wool overcoat as a great cold-weather option to give your outfit a polished look.

• Charles Tyrwhitt Wool Overcoat in Navy [$499; charlestyrwhitt.com]
• Wellen Recycled Cotton Headlands Sweater in Heather Bone [$128; huckberry.com]
• Banana Republic Tapered Perfect Flannel Dress Pant in Tan [$45; bananarepublic.com]
• Blundstone Classic #585 Chelsea Boot [$230; blundstone.com]