Lenny's Shoe & Apparel - Work Clothes, Boots and Outdoor Gear

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Featured brands

Featured winter gear

Carhartt Steel

We are the Exclusive New England dealer for Carhartt Steele

Shop Carhartt Steel

Limited Edition Lenny's Exclusive Darn Tough!\ \ Shop Now

Seasons change. Your adventure continues.\ \ Shop Kuhl

Sitka Gear: Built for the Hunt\ \ Premium hunting apparel and gear engineered for backcountry performance. \ \ Shop Sitka

Left Featured Collections Right

\ \ Blundstone](/content/collections/blundstone/index.html)

\ \ HOKA](/content/collections/hoka/index.html)

\ \ New Balance](/content/collections/new-balance/index.html)

\ \ Birkenstock](/content/collections/birkenstock/index.html)

Rugged workwear built for durability, comfort, and grit.\ \ Shop Carhartt

From versatile clogs to chic booties and everyday casual shoes designed for the way you live.\ \ SHOP Dansko

Best Sellers

Darn Tough Vermont Women's Bear Town - Aqua\ \ $24.99 USD

5.0 / 5.0

1 review

Darn Tough Vermont Women's Mother Clucker Crew Lightweight Lifestyle Sock - Sunny\ \ $24.99 USD

5.0 / 5.0

1 review

Darn Tough Vermont Men's Hiker Boot Midweight Hiking Sock - Black\ \ $27.99 USD

5.0 / 5.0

1 review

\ \ 30% off](/content/collections/best-sellers/products/carhartt-mens-washed-duck-work-dungaree-moss/index.html)

Carhartt Men's Washed Duck Work Dungaree - Moss\ \ FromOriginal price$49.99Sale price$34.99 USD\ Sale30% off

5.0 / 5.0

2 reviews

Darn Tough Vermont Men's Hiker Micro Crew Cushion - Black\ \ $25.99 USD

5.0 / 5.0

1 review

Vermont Glove Vermonter Work Glove\ \ $115.00 USD

5.0 / 5.0

1 review

Darn Tough Vermont Women's Bear Town - Purple\ \ $24.99 USD

Darn Tough Vermont Men's VanGrizzle Midweight Hiker Boot Sock - Charcoal\ \ $27.99 USD

Shop Best Sellers

How We Compare

Feature		### Competitors
30-Day Hassle-Free Returns
Vermont Customer Support Team
Retail Stores in VT and NY
Free Personalized Shoe Fitting
Workwear Experts for 35+ Years

\ \

Sales & Events at Lenny's

Find information on annual sales like Black Friday, the Charity Sale, our Sock Sale, the big Anniversary Sale, and special events such as Lenny's Loot, Nurses Week, Trunk Shows and more!

SEE CURRENT SALES & EVENTS

From the Lenny's Blog

\ \ Lenny’s Shoe & Apparel, Darn Tough Vermont, and Smartwool Team Up Again](/content/blogs/community/lenny-s-community-impact-21-000-in-sock-donations-and-support/index.html)

WILLISTON, VT – For the 16th year in a row, Lenny’s Shoe & Apparel, Darn Tough Vermont, and Smartwool have joined forces to donate more than $21,000 worth of socks...

September 10, 2026

— Lenny's Web

\ \ Cluck Yeah! Skiing Chickens Sock It to Hunger](/content/blogs/community/cluck-yeah-skiing-chickens-sock-it-to-hunger/index.html)

Sales of Lenny’s exclusive skiing chicken socks hatch $6,078 donation for neighbors in need BARRE, VT – Lenny’s Shoe & Apparel is shaking its tail feathers with a $6,078 donation...

January 30, 2026

— Lenny's Web

\ \ 15 Years Strong: Lenny’s Shoe & Apparel Marks Milestone with $24,000 Donation](/content/blogs/community/15-years-strong-lenny-s-shoe-apparel-marks-milestone-with-24-000-donation/index.html)

Thanks to community support, annual Charity Sale brings total donations to more than$313,000 for local hunger relief BARRE, VT — On Saturday, October 18th , local shoppers came together to...

October 31, 2025

— Lenny's Web

Welcome to Lenny's Shoe & Apparel

Whether you've been buying your outdoor gear from us since 1990 or this is the first time you've heard of us, we thank you for visiting our website today. At Lenny's Shoe & Apparel, our goal is to help you gear up for your next big adventure. We're much more than a Vermont shoe store - we're Vermont's favorite destination for work clothes, work boots, outdoor apparel, hiking boots, and footwear of all kinds! Plus, we carry a wide selection of practical & stylish clothing for the whole family.

We're proud to offer top brands like Carhartt, KEEN, Bogs, Dansko, Timberland Pro, Crocs, Chippewa Boots, Kuhl, and more - including local, Vermont-based businesses like Darn Tough Vermont socks. If you need footwear or clothing for your next adventure, whether you're on the job site or on the trails, make us your first stop for everything you'll need to stay comfortable, fashionable, and protected.

Here at Lenny's, we've been outfitting working folks & families since 1990 - and we fit you right!

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30 Days Return Policy

Rated 4.5+ by Customers

Customer Service

Inside Lenny's

About Us

Contact Us

Web Office: 2121 Essex Rd, Williston VT 05495

[+1 (802) 879-6640](te:+1 (802) 879-6640)

web@lennyshoe.com

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