Okay, We Think We've Finally Nailed Down Our Fall Looks

It’s really hard to beat those first fall days when the air is crisp and the leaves are turning. As is customary this time of year, the change in season has us eagerly planning cozy fall getaways and staycations. We’re envisioning apple-picking, glamping, and embracing the Scandinavian concept of hygge—think candlelit conversations with friends replete with snug blankets and bottles of red wine.

And with planning an itinerary comes planning the outfits to go with. It's time to swap out those strappy sandals for booties that are the perfect balance of comfort and style. The million dollar question is: Which ones? For the answers, we're looking to Christina Caradona of Trop Rouge, Justin Livingston of Scout Social, Moti Ankari of The Metro Man, and Serena Goh of The Spicy Stiletto.

These New Yorkers have been friends for more than five years, and decided to take their favorite pairs of Clarks out for a weekend spent in Manhattan’s most scenic destinations. 

Ahead, see the season’s most covetable shoes for your own weekend explorations. After all, those boots were made for walking, right? 

Goh is known for staying true to her minimalistic style, and she tends to opt for streamlined looks with a feminine touch. For traipsing through Central Park, she either opts for an on-trend check blazer and ankle-grazing denim, or an oversize cream sweater over a long black dress—either look pairs perfectly with her lace-up block-heel booties.

“I love making footwear the focal point of my outfits, and I tend to gravitate toward monochromatic shades,” she explains. “Fall layering is all about playing with texture; I like to combine a detailed piece like this dress with a minimalistic cozy sweater.” Her laid-back luxury look, which pairs effortless staples with more structured pieces, is ideal for staying chic and comfortable exploring New York City’s green spaces.

An expert on effortless menswear, Justin relies on his Chelsea boots to anchor casual fall outfits, whether he's heading upstate for the weekend or simply making a point of enjoying the city. “No fall getaway is complete without a generous helping of plaid shirts, chunky sweaters, and perfectly worn-in boots,” he explains. “These Chelsea boots are one of the most comfortable pairs I’ve ever owned.”

Here, he layered a lightweight plaid shirt over a tee—the perfect combo for when there’s a chill in the air but it’s not quite cold enough for a jacket. The suede boots add a touch of sophistication to his look, don't you think? “I love that Chelsea boots have made an immense comeback in menswear. They’re comfortable and easy to slip in and out of, and they elevate any comfortable look.”

Caradona is a self-proclaimed “comfort first” person, and she admits she tends to underpack for her travels—“I’ve been known to bring only one shoe instead of the complete pair,” she tells us. Packing for a weekend away, she has only three requirements: a scarf (she knows she’ll complain if she’s cold), a vintage blouse (this one is from Paris), and the Clarks Trace Fawn boots she’ll wear with every outfit. 

“Honestly, I rotate four pairs of shoes during fall, and three pairs are boots,” she admits. “You also have to own Chelsea boots like this brown pair from Clarks, heeled booties like Serena’s for more polished looks, and comfortable lace-up boots like the pair I wore for exploring the city.” To show off her footwear, Caradona cuffs her denim and adds a subtle pop of color with pink socks. “I always think less is more; if you feel good in what you wear, it’s going to show,” she tells us.

Serena’s longtime friend, men’s fashion blogger Moti Ankari, insists on traveling light. “I make sure to pack these boots, as they’re super versatile and go with any fall look,” he explains. For a day spent outdoors in the city, he pairs his boots with a few of his favorite fall trends: a leather moto jacket, a floral shirt, and light denim. His secret to fall layering? “Mix as many textures as you can,” he advises. The result is an understated look that packs serious style. 

Want to snag stylish boots that will pull together any of your favorite fall looks? Clarks has you covered this season.