Timberlands are back. Don’t pretend you didn’t see them on the guy in front of you while you were in line to see if Starbucks is still carrying the trenta. Perhaps you saw them on the girl meeting her friends for drinks downtown. Some of you might be thinking, “Now that you mention it…” and it’s true: They’re back. We’ve all witnessed the ’90s make a colossal return in the past year (love them or hate them, flannels around the waist, crop tops and acid-washed jeans have been everywhere), and it seems the decade’s latest resurrected trend includes the classic worker boot that most of us wear just for fashion’s sake.

Plus, I love all the new sneakers currently happening in streetwear but we’re in Colorado and there’s snow, slush and ice outside. Investing in new pair of Adidas, New Balance or Nikes can wait until spring. These babies are sure to be a stylish and actually useful purchase for winter. I know, I know–you weren’t prepared for Timberlands to come back and now you don’t know how to wear them. Luckily, there’s no need to panic.

Here are four ways to wear Timberlands:

#1. Dress them up

Image Courtesy of Maxime Huillo

Image Courtesy of Maxime Huillo

So you’re more buttoned up and you still want to wear Timberlands. A denim shirt, tie and blazer are a great way to feature the boots in your next outfit.

#2. Dress them down

Image Courtesy of Will Barton's Instagram

Image Courtesy of Will Barton’s Instagram

If you’re more of a T-shirt and jeans kind of guy, that’s no problem. Simply throw on a jacket on top of your regular threads to complete your outfit.

#3. Going out

Image Courtesy of Contemporary Clothing

Image Courtesy of Contemporary Clothing

So you’d like to get some sake bombs with your girlfriends. It’s the perfect occasion to look chic and add an urban twist into your #OOTN.

#4. Staying in

Image Courtesy of Lyn Patero's Lookbook

Image Courtesy of Lyn Patero’s Lookbook

Now you’re having dinner at your friend’s house but you don’t want to glam up. A cozy knit sweater and the boots will do.


I’ve worn my Timberlands (Christmas present, thank you very much) on lazy days with just a crewneck sweater and jeans and also spruced up with a black button-up and leather pants. How will you add your own twist? There are also select pairs in colors such as pink, red and teal–for those feeling extra bold. Try them out, and you’ll be surprised how versatile and stylish these boots are.