Q & A with Stylist Samantha McMillen

Expert advice

For us, fall and winter are the true seasons for style: stylish boots, trench coats, warm parkas, classic sweaters, rugged boots and more. This season, we decided to seek out professional advice for some tips on how to pair our signature items together.

Celebrity stylist Samantha McMillen has dressed the likes of Johnny Depp and Natalie Portman. After working in fashion magazines and designer collaborations, she quickly became a favorite of celebrities who wanted to look their best.

This season, she joined Timberland on the Modern Trail and gives us a lesson in winter layering.

Why did you decide to collaborate with Timberland on our Made for the Modern Trail Campaign?

I am drawn to Timberland’s rugged heritage and tailored, fitted and modern elements. I am particularly drawn to how the brand combines versatility, comfort and style with its footwear, apparel and accessories. This season, the Fall 15 collections feature more refined city looks with details that make the pieces really unique.

I especially like Timberland’s commitment to being green by using renewable, organic and recycled materials wherever possible.

What are your tips when transitioning a look from day to night?

Changing your shoes is my way of completely changing your look. Going from an awesome flat moto boot like the Savin Hill Ankle boot, to a boot with a chunky heel, will completely amp up your style and change your look from day to night.

For men, I feel many of Timberland’s shoes go from day to evening, so you can throw on a tie to go to a cocktail party in the evening and it will still make for a great ensemble with your shoes or boots. These Chukka boots are a particularly great fit for a transitional look.

The fall and winter seasons are all about layering. What tricks do you have for layering items so the effect isn’t bulky?

The Fall 15 line lends itself perfectly for those tricky transitional days that can’t make up their mind. To combat the changing weather, take advantage of the range of versatile layering pieces that won’t cramp your style. Pick up a lightweight mac with HyVent waterproof technology for a classic style that keeps you dry and looking good.

What are your favorite fall items that easily transition into winter?

The Timberland Boot Company boots transition well from day to night. Wear the Wodehouse Wing Boot at the office, and then straight to dinner for a polished look that is subtle and stylish.

I love the Men’s Heritage 6-Inch Warm Premium Waterproof boot – the worn-in look harkens back to vintage workwear.

For women, a riding boot is a must-have winter shoe. I love the Savin Hill collection with handcrafted detailing. The classic silhouettes are the perfect complement to cooler-weather ensembles.

What’s the best piece of styling advice you’ve received?

Be yourself when you are creating an outfit, and don’t ever leave the house being uncomfortable in anything you’re wearing.

Timberland is known for its durability and performance. How important is it to have fashionable items that are also functional?

It’s extremely important! You don’t look at Timberland and think. “It screams performance.” You wear it because you like the way it looks and yet there is so much hidden technology across the collections like Anti-FatigueTM footbeds or HyVent® waterproof technology in apparel, so you don’t even have to think about it.

Timberland strives to be a green company. You mentioned you admired our commitment to the environment. What stands out to you?

As a company I have always admired Timberland, and I respect the way they operate; it aligns with my own beliefs. Here are some facts that really stand out to me:

Through the use of recycled PET, 185 million plastic bottles have found new life in footwear from 2009 to 2014.

In 2014, 79 percent of all Timberland footwear product incorporated recycled, organic or renewable materials.

Also, 99 percent of Timberland’s footwear leather volume was sourced from a silver- or gold-rated tannery, earning high marks on key environmental metrics.

Recently, Timberland launched Timberland Tires – the first line of tires purposely created to be recycled into footwear outsoles at the end of their journey on the road.

It’s fantastic to work with a company that I feel good about – they put as much effort into design and function as they do into implementing green practices. 

Get Samantha’s fashion hacks in her round-up of her must-have pieces for the season.