­Each season, we ask a few Timberland employees pick their favorite footwear styles to wear in a “Staff Picks” photoshoot and describe what they love about the product.

Model: Henry Gilbert – Buying Coordinator

As Buying Coordinator, Henry Gilbert keeps an eye on the aesthetic of the Timberland brand. “I appreciate the menswear staples that have stood the test of time without growing stale: leather boots and broken-in denim.”

Henry picked the Killington Leather Hikers — his third pair of Killingtons. “I love these shoes because they’re lightweight, super comfortable, and stay true to the Timberland vibe of quality, rugged sportswear. They make a great alternative to heavier boots for the warmer summer and fall months.” 

To go with these versatile and stylish boots, Henry chose the Reversible Bomber Jacket. With two unique looks, this lightweight outerwear staple is two looks in one. He was drawn to its versatility — great for a night out on the town, and the perfect jacket for a weekend getaway when you want to pack light. 

Model: John Franklin – Sr. Designer, Footwear 

The Boot Co. Wodehouse Chukka was an easy pick for John. “I tend to opt for classics due to the longevity of style.” John’s wardrobe inspiration comes from many different places, including architecture, music, furniture, fashion, posters, transportation and art — things that transcend time.

John is a Senior Footwear Desginer at Timberland, so he gets to channel his inspiration into the Timberland line. One of the things that John values about Timberland as a company is the commitment to community values. “It’s good knowing that Timberland has been a trail blazer for human rights, ethical and ecological responsibility and green living, before it became a trend in the marketplace.”

Can’t get enough of our staff picks? Head over to this post to check out some of our women’s top styles for the season.