Top Picks for Men

Fall Footwear Favorites, handpicked by the staffers
who design them, style them & live in them.

Brian's Pick

Ecommerce Analyst

BRITTON HILL WINGTIP BOOTS

“These boots are perfect with jeans — wear them cuffed to show them off or down for a more relaxed look."

Favorite Fall Trend:
"Crewneck sweaters!”

Henry's Pick

Footwear Merchandising Coordinator

KILLINGTON HIKERS

“The perfect combination of a lightweight sneaker and a rugged hiker - a great fall alternative to heavier boots!”

Fun Fact:
“Last year, I was invited to give a presentation at the Museum of Fine Arts in Boston.”

Clay's Pick

Footwear Merchandising Coordinator

SNOWDEN PEAK 3-IN-1 M65 JACKET

“The Snowden Peak is so adaptable. I know that I'll always have the right jacket for any weather."

Fun Fact:
"My first day working for Timberland was on Black Friday at an outlet store. It was crazy!”

Bryan's Pick

Senior Business Analyst

EAGLE BAY BOOTS

"These are a fresh take on boots, with rugged good looks and a lightweight, flexible feel."

Favorite Fall Trend:
“Solid flannel shirts that work for the office but are tough enough for outdoors.”

John's Pick

Footwear Designer

WODEHOUSE CHUKKAS

"The Wodehouse has a timeless appeal that's clean, comfortable and requires no break-in time."

Favorite Fall Trend:
“Anything that's designed for longevity, and wears well over time.”

Rome's Pick

Men’s Footwear Designer

FLYROAM LEATHER SPORT CHUKKAS

“These shoes are light, fast and resilient with an urban feel…it's something totally new from Timberland.”

Favorite Fall Trend:
“The textured, layered look, with rich colors to give a sense of warmth."