When we all made our “ins and outs” lists for 2024, I listed “closet staples” as in and “one-time wear” as out. USA Independence 1776 USA WWI Champions 1918 USA WWII Champions 1945 shirt And nothing says “closet staple” quite like a pair of Timberland boots. For 50 years (literally), these shoes have reigned supreme among native New Yorkers and transplants alike as the quintessential city boot that anyone can wear in any kind of weather to just about any job. New York City is one of the most unpredictable places, but one thing I can always count on is spotting a pair of Timberland original six-inch work boots on the subway, in the park, or at the crosswalk. Even when I don’t spot them on my daily commute, I see them in paparazzi photos of Jennifer Lopez, Rihanna, and Emily Ratajkowski. As corny as it sounds, I feel most like a New Yorker when I’m wearing a pair of Timberland boots. Cult-classic status clearly isn’t enough for the team at Timberland because they continuously launch new and exciting variations of this iconic shoe, including collaborations with Jimmy Choo and Veneda Carter and an upcoming collab with Louis Vuitton. Let’s just say Timberland already has all of my attention (and money) in 2024. My latest obsession is the Indigo Suede Icons Collection in partnership with C.F. Stead, a renowned English tannery best known for producing the world’s finest leathers and suedes. These are comfortable, waterproof, and the perfect twist on the original yellow boots. You’re going to continue to see these shoes dominate this year, so I figured I’d leave you with some inspo. If you’re looking for fresh ways to style Timberland boots that feel so 2024, just keep scrolling.

USA Independence 1776 USA WWI Champions 1918 USA WWII Champions 1945 shirt, hoodie, sweater, longsleeve and ladies t-shirt

Instagram isn’t just a space for 20-something DJ-slash–fashion bloggers anymore, USA Independence 1776 USA WWI Champions 1918 USA WWII Champions 1945 shirt as there are countless influencers over 40 who are just as influential. Style is now finally truly recognized as being ageless, and 50-something Instagrammer Grece Ghanem shows that whatever decade you were born in, you can pull off neon trousers and zebra mesh tops. Grece might dress like she’s on the front row at fashion week every single day, but her day job hasn’t always been in the fashion industry—she’s a personal trainer based in Montréal. Grece has a real ability to make intimidating trends look timeless and wears bright colors and animal print better than anyone else I follow. Her 2020 look revolves around colorful knits, wide-leg statement trousers, mesh printed tops and pleated skirts, but she also has a knack for making simple outfits look impactful. One of my favorite Grece looks is flared jeans with a blue Oxford shirt. Often the most uncomplicated ensembles pack the chicest punch. The latest of these simple combos is now is becoming every bit as ubiquitous. Enter: super-relaxed tailoring, the outfit trend we can barely go an Instagram or Pinterest scroll without spying on our favorite influencers. As much suited to a stroll through a Moroccan market as to the lunch spots of downtown Manhattan, this combination of an oversize shirt mixed with loose-fitting tailored trousers screams easy-breezy. There’s only one rule to the trend: Keep your separates relaxed and minimal. Ensure your shirt is a few sizes too big, and pair with paper-bag, high-waisted trousers, palazzo styles, or an oversize subtle flare (blogger Ada Oguntodu expertly demonstrates this option below). As for your palette, neutral works best, but no one’s getting a slap on the wrist if a dash of color is what you so desire. Below, we’ve rounded up prime inspiration for the best trouser-and-shirt combinations in town.