Comfortable Casual Footwear
Rosemont, MI
Custom Orthotics
Special Orders Available
Free Shipping on Orders Over $100
Hours:
Casual Footwear for Every Occasion
At Chester Boot Shop, we understand that comfort and style go hand in hand when it comes to casual footwear. We've been providing exceptional service since 1948, offering a wide range of options to suit your everyday needs. Whether you're looking for work boots, western boots, hiking boots, or biker boots, we've got you covered. Our selection includes:
- Comfortable sneakers
- Stylish loafers
- Versatile slip-ons
- Durable sandals
- Casual dress shoes
We also offer a variety of hats and apparel to complement your footwear choices. Visit us to find the perfect casual shoes for your lifestyle.
Why Invest in Quality Casual Footwear?
Investing in high-quality casual footwear is essential for your comfort and foot health. Here's why you should prioritize good casual shoes:
- All-day comfort for work or leisure
- Proper support for your feet and posture
- Versatility for various casual occasions
- Durability for long-lasting wear
- Style that complements your wardrobe
At Chester Boot Shop, we're committed to helping you find the perfect pair of casual shoes that meet your needs and exceed your expectations.
Why Choose Chester Boot Shop
When it comes to casual footwear, Chester Boot Shop stands out from the crowd. Here's why customers have been choosing us for generations:
- Exceptional service since 1948
- Locally and family-owned business
- Quality service and merchandise
- Special orders available
- Shoe repair services
- 1 to 7 days for product arrival
- Same or next business day shipping
- Exchange or refund within 30 days
- Free shipping on orders over $100
- In-house leather belt production
- Custom orthotics available
Our commitment to quality and customer satisfaction sets us apart. We're not just selling shoes; we're providing comfort, style, and peace of mind with every pair.
Contact Us
Ready to step into comfort and style? Chester Boot Shop is here to help you find the perfect casual footwear. Our knowledgeable staff is ready to assist you with everything from sizing to style selection. We're passionate about providing you with the best possible shopping experience, whether you're looking for everyday shoes or something special for a casual event. Don't let uncomfortable shoes hold you back – visit us today and discover the difference that quality casual footwear can make in your daily life.
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A LEGACY OF GRIT SINCE 1948
Since 1948, Chester Boot Shop has been the premier source for durable, top-quality boots that can withstand any job. Today, our family-run boot shop in Roseville, MI, offers world-class service and uncompromising quality—much like the boots and shoes we carry. We're proud to have helped outfit Detroit for more than 75 years!
Whether you need western boots, biker boots, hiking boots, or Dr. Martens, we have the perfect size and style. From American-made products to globally recognized brands, we are the ultimate authority in tough footwear for tougher people.
Chester Boot Shop's Offerings

Hiking Boots
To enjoy the great outdoors and city, Chester Boot Shop offers excellent walking and hiking boots with superior support & traction.

Cowboy Boots
Embrace the spirit of the West with Chester Boot's western boots, known for their style, intricate designs and authenticity.

Causal
For everyday wear and great style, Chester Boot Shop offers a wide selection of casual footwear from slip-ons to loafers.

Hats
Chester Boot Shop offers a variety of hats, including cowboy, caps, fedoras, and more, as well as hat shaping and cleaning.

Apparel
Chester Boot Shop offers a variety of apparel, including shirts, pants, hoodies and jackets. Great for work and play!