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How to Be Stylish AND Comfortable, According to Celeb Stylist Samantha McMillen

The Timberland brand ambassador shares the keys to real girl style.

When you think about "style" and "comfort," they don't always go hand-in-hand. Wearing 5-inch stilettos with culottes and a crop top doesn't exactly seem like a breezy way to spend an afternoon, unless you're basically Gigi Hadid. But it doesn't have to be that way. 

Celebrity stylist and Timberland brand ambassador Samantha McMillen has worked with big stars like Dakota and Elle Fanning, Johnny Depp, Carey Mulligan, and more, and knows all about red carpet fashion. But she also knows the secrets to looking fantastic without compromising comfort — for date night, frolicking around in the snow, you name it.

How to Be Stylish AND Comfortable, According to Celeb Stylist Samantha McMillen
Courtesy Samantha McMillen

Samantha answered our questions about real girl style and here's what we learned:

What are 5 key items that an everyday woman could wear and still feel comfortable/casual?

"I always say comfort is an essential element to a great outfit.  I try to find clothes that are both stylish and comfortable. A few of my go to pieces are black leather leggings, solid color oversized cashmere sweaters, great boots, a blanket cape (for that bohemian feel) and a great versatile coat...like Timberland's all black trench coat.

How to Be Stylish AND Comfortable, According to Celeb Stylist Samantha McMillen
Timberland

These are pieces that can be mixed and matched with just about anything and can all be worn as part of some great layered looks. I occasionally throw on a hat to complete that bohemian casual look I love so much."

 

If you're not ready for an over-the-knee boot, what's an alternative for a fierce date night option?

"For date night, a lower heeled boot paired with some high waisted wool shorts, tights, a cropped sweater and a cape or mid thigh coat is a great look. Or substitute the top part with a fashionable short dress and tights for a softer look.

 If you’re not comfortable with over-the-knee boots, Timberland has a great mid calf option that is easy to wear and flattering. The Stratham Heights Boot is the perfect classic mid boot because it’s versatile and ready to wear. It can go from day to night. Every girl needs this in her closet."

How to Be Stylish AND Comfortable, According to Celeb Stylist Samantha McMillen
Timberland

 

What are a couple key items to have in your closet this winter?

"A great transitional winter boot is important during the winter season. Go for a boot with a comfortable chunky heel and traction. A beautiful winter hat is always good for those who are comfortable wearing hats. The camel color is also big right now. A stylish camel colored coat is a staple for winter and a great alternative to black."

 

What's one item you should invest in for the cold weather season?

"Updating your classic winter coat is a great investment for the season. An elegant slightly oversized coat that you can go day to evening with is a great choice. I love the MaxMara camel Marilyn Monroe inspired coat."

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