Timberlands have always been a wardrobe staple for me—mostly because, as an avid hiker, I know they can actually survive a full day of activity. We already know they’re the unofficial uniform for a slushy February in New York, but lately, it’s the styling on OOTD that’s been catching my eye. The looks coming through are a reminder that Timbs have way more range than we give them credit for.
Your Timberlands have more range than you think. Some of the best outfits come from combinations that look "wrong" on paper. A silk slip dress with chunky boots. Lace socks with a heavy sole. Boat shoes paired with a floor-grazing denim skirt and a baker boy cap.
The secret to making an outfit stand out is not being afraid to lean into the unexpected. Timberlands are a loud shoe, and when you put them on with something lighter or more feminine, it gives that ultimate "City Girl" energy. These are the combinations that actually make you stand out in a crowd.
The easiest way to style the classic wheat Timbs? Keep it easy with a white graphic tee tucked into khaki cargo shorts and a red plaid flannel tied at the waist. It’s the perfect "off-duty" look for a Saturday spent shopping on Melrose.
We’re also seeing the boot fully transition into summer. Think: an oversized polka dot blazer paired with denim cut-offs and a structured brown belt. Or, for something more playful, a pleated mini skirt and stacked gold jewelry. In both cases, the shoe is the main character.
Ava is a Creative Editor at OOTD. She graduated from the Fashion Institute of Technology and now covers your favorite fashion figures, events, and trends.
The dark burgundy boat shoe is having a big moment right now, and the OOTD community is proving exactly why.
Since stripes are also having their own revival, the two are a perfect match. I’m obsessed with this look layering a classic Breton stripe under an oversized grey coat, adding a lacy thigh-high stocking, and letting the dark burgundy shoe act as a pop of color.
If you want to go the neutral route, try wide-leg cream trousers with a dark suede blazer and a green sweater tied at the waist. Add on a baseball cap to walk the streets of Paris effortlessly.
Timberlands were built for a purpose, but these shoes work whether you’re in a warehouse or a wine bar. Whether you’re grabbing the 6-inch boots in the dead of winter or the boat shoes for a July heatwave, the logic remains the same: don’t be afraid to try something new (even if you think it looks weird)!
Check the inspo on OOTD, pull your pair out of the back of the closet, and start experimenting. Your Timbs are ready for whatever’s on your calendar.
