'90s Style Timberland Boots Make a Comeback

Timberland boots are one of the most recognizable shoes of all time, and in the fashion world they're more popular than ever. Launched 40 years ago as a durable, waterproof shoe for workmen, the wheat-colored boots were reappropriated by members of the hip-hop community like Wu-Tang Clan, DMX, TLC, and Aaliyah in the 1990s. Producer Timbaland even received his nickname from his fondness for the shoes. A decade later Tims were a style style staple. Jennifer Lopez famously rocked Timberland-inspired heels in her 2002 "Jenny from the Block" music video, and Beyonce and her then-boyfriend Jay-Z wore matching Timberland-style boots in their "'03 Bonnie & Clyde" video. Victoria and David Beckham often wore matching Tims. With the recent resurgence of '90s fashion trends, Timberlands have been spotted on the feet of trendsetters like Rihanna, Khloe Kardashian, and Kanye West. Beyonce even Instagrammed a photo of her family's Tims (yes, baby Blue Ivy wears them too).

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Timberlands may add a toughness to an outfit, but with their yellowish color, bulky rubber sole, and bold grommets they're a somewhat surprising choice for fall's must-have footwear. Are they really stylish? And how can the average woman pull them off in a cool--or dare we say chic--way this season. We tracked down celebrities, models, designers, and style experts at New York Fashion Week to weigh in on the unexpected shoe trend.

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The celebrities we interviewed were totally on board:

Mary J. Blige - Oh my god, I've worn them all my life. Right now since they're coming back, you could do Timberlands with a mini skirt. You could wear them with a pair of jeans and a leather jacket. I wouldn't try it with a really nice dress.

Jessica Alba - I grew up with Doc Martins. They're a little different, but I think girls could pull [Timberlands] off, of course. J.Lo! [Laughs]

Margarita Levieva, "Revenge" star - I love Timberland boots. I'd probably wear them with either a short Scottish skirt kind of thing or maybe with some tights and a baby doll dress, like take me back to the '90s would be fun.

Sammi Giancola, "Jersey Shore" star - I love them! You could wear them with anything, but I think I'd like Tims with a nice jean. How hysterical would it be to see Tims and overalls?

All the fashion insiders and stylists we spoke to felt Timberlands were a must-try:

Nina Garcia, "Project Runway" judge and Marie Claire Creative Director - I am a big fan of American classics. Timberland, L.L. Bean, I think there's something so wholesome about some of these American brands, I don't think you need to style them. I think they're very cool. It's the same way when Marc Jacobs in his grunge collection showed the Birkenstocks, it was so American and so ingrained in us, and showcasing those items is fabulous. Right now this generation is so savvy and so stylish they could pull off anything.

June Ambrose, celebrity stylist - I love taking things out of context. My assistant is very preppy and collegiate, and I would put my Timberlands with something that's completely of that nature. Go rogue with it! Do it with something preppy! I think you'll give it a different voice.

Brad Goreski, stylist and Bravo reality star - That's such a late '90s, early '00s Jennifer Lopez moment. I totally think girls could pull them off. Girls are doing high tops, Adidas, all kinds of stuff, so I think it's a super cute look with pants. I think it would probably work better with a dress, a slouchy trouser, you know, keep it looking street.

Phillip Bloch, stylist - Yes! Tims, as we call them in the hood [laughs], you know, in the streets. I've worn them for years, I'm a big fan. I like them whether they're going for the chic feel, or they're going for the urban street feel. [For women] I think it's really about the top. You've gotta wear them with a sexy jean, or something cute and short, but then you've gotta wear a glamorous top. It's about mixing the glamorous with the sort of urban, rugged feel. I think Timberland is one of those brands that manages to go from urban to rough and rugged. They have the country vibe and the city vibe all at once, so when you put a little infusion of chic, all the better.

Jay Manuel, former "Americas Next Top Model" star and fashion critic - Are you kidding. A pair of Timberlands? Of course everybody can wear them. Most people love to dress it down, but I think it's kind of fun when you're wearing, especially right now pattern blocking is huge, so if you wear some fun, big patterns like an oversized houndstooth pair of pants, or a cool sweatshirt with a graphic on it and a pair of Tims? Totally. It works.

Models admittedly can pull off anything, but they wouldn't mind giving Timberlands a go:

Coco Rocha, supermodel - I wouldn't mind wearing them. I think it's up to how you style yourself. If you're a cutie patootie and you wear dresses all the time I'm sure it's not your look, but if you're into more of a rock and roll sort of thing, then I think you can pull it off. I would probably wear some tight pants, a little loose on the top, a baggy sort of jacket, and play around with makeup. Make it a little more cute in your makeup and your hair.

Jessica White, model
- I used to wear Timberlands when I was younger. I hate following trends, but I would wear them the way I did in 1999 when I was still in high school with a pair of baggy sweatpants-which are very popular right now-and a great T-shirt. Now I'd rather wear heels with my sweatpants, but Timberlands look great on those who wear them, like Rihanna does a really great job at styling them.

Some big name designers think Timberlands are downright alluring:

Max Azria, designer of BCBG and Herve Leger - It could be very stylish if you do a contradiction with a very feminine dress with these tough shoes. The balance is fantastic and very sexy.

Catherine Malandrino, designer - If you think it looks sexy it's all about an attitude. I never have an opinion of good taste or bad taste, you need to be inventive. I feel a creative woman should be audacious. You should look at it it twice and dare to make it a woman.

But other designers were skeptical about the resurgence of Tims:

Rebecca Minkoff, designer - No. Don't do it. I think it's a great company, but I am not drawn to the shoe personally.

Rebecca Taylor, designer - I know the guys at my gym wear them on Flatbush Avenue in Brooklyn. I'm sure someone could [make them stylish]. I don't think I could. Doc Martins may be more fun. It's the yellow with the Timberlands, but if they weren't yellow I could totally see it.

Have you worn Timberland boots in the past, or will you be wearing them this season? Let us know in the comments. For more fall fashion do's and don'ts, check out the video below.

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