New Yorkers Are Notorious for Adopting Trends Early—3 Fall Outfits They’re Already Wearing

- Advertisement -

Welcome to Word on the Street, a quarterly series in which one editor takes to the streets of New York City to snap her favorite fashion moments and shop them out just for you.

As a Brooklyn resident, whenever I want to get a pulse check on trends I should be investing in, I simply step outside. My neighbors are some of the best-dressed people I know, and more often than not, they’re wearing the trendiest pieces of the season before it’s even begun. Right now, we are in the “fake fall” stage of late summer, when the weather finally starts to cool down as we transition into autumn. I can finally pack away my flip-flops and sundresses and pull out my suede accessories and light jackets (for now, at least). With this glorious forecast in my favor, I took the opportunity to snap a few pictures of my neighbor, friend, and fellow editor, Anneliese Henderson. Whether she’s going on long walks with her pup Rosie or heading out on a date night with her husband, these three Free People looks perfectly encapsulate her early-fall style. To shop her outfits and see the trends she’s already wearing (like the natural New Yorker she is), keep reading.

What does the perfect fall day in Brooklyn look like for you? What are you wearing for the occasion?

Anneliese Henderson: A perfect fall day involves me and my dog, Rosie, waking up (or her waking me up) to a crisp, but sunny morning. The key to my perfect Brooklyn day is comfortable shoes, and a pair of Timberlands is the ultimate option. They’re durable (have you ever had an 80-pound dog step on your foot?) and comfy enough that I can walk around. The first stop on our day’s adventure would be a coffee shop for a pumpkin spice latte (yes, I am that girl) and a pup cup for Miss Rosie. After that, we’d go to our favorite park, where Rosie and her friends love to run around. Then, a nap (for both me and her) before heading out to a cozy dinner with my husband. I paired my boots with my go-to combo: Jeans, a white tee, and a faux-leather jacket. It’s an outfit I will always turn to because it can take you from day to night.

Free People We the Free Hera Vegan Leather Jacket

Free People We the Free Nova Tee

Free People We the Free East Bay Cuffed Jeans

Free People Cruise Oversized Aviator Sunglasses

Timberland Stone Street Mid Lace-Up Waterproof Boots

Does this look play into any fall trends you’re incorporating into your personal style this season?

AH: I just moved from L.A. to NYC, so I’m excited to experience actual seasons. However, native New Yorkers have been telling me that the chilly days won’t happen for a while. In the meantime, I’ll pair long shorts with layers, like my favorite fall jacket—an oversize barn jacket. I love the relaxed, casual feel. Plus, it just makes every outfit look exponentially cooler. I love adding a boot to a shorts outfit, so of course, I opted for my Timberlands.

Free People We the Free Denim Barn Coat

Free People We the Free Hazy Tee

Free People We the Free Montana Shorts

Timberland Stone Street Mid Lace-Up Waterproof Boots

Timberlands are a staple in a New Yorker’s wardrobe. How did they inspire this last look?

AH: For my last look, I wanted to go for a preppier feel. And luckily, Timberland does more than just iconic boots—boat shoes are on the style menu as well. When I saw them, I knew I’d pair them with socks and a skirt (like I said, I’m leaning into preppy!)—but finding this silky, Free People button-down was the cherry on top. Brown suede is the trend of the moment (just ask any Who What Wear editor), and this skirt was the perfect way to lean in. I received compliments the second I walked out the door. The whole look felt like it was made to go together.