Chestertown's Trusted Style Destination

Hello, Chestertown! Let's find your perfect fit.

For generations, Jerry Moe's has been the place where men come to look and feel their best. From sharp suits to weekend casual, we've got you covered with quality pieces that actually last.

335 High St, Chestertown
Jerry Moe's Menswear interior showing quality men's clothing on display
Classic men's suit selection at Jerry Moe's

Est.
Chestertown

Shoe collection at Jerry Moe's Menswear

Quality
Guaranteed

Our Story

More than a store—
it's your local style partner.

When you walk through our doors on High Street, you're not just browsing racks—you're getting personal attention from folks who actually know their way around a wardrobe. We've built our reputation on helping men in Chestertown look sharp for weddings, job interviews, date nights, and everything in between.

No pressure, no upselling—just honest advice and a curated selection of brands that hold up wash after wash and season after season. That's the Jerry Moe's way.

Expert Fitting

We help you find clothes that actually fit your body.

Local Favorite

Proudly serving Chestertown for years.

What We Offer

Everything you need,
under one roof.

Suits & Blazers

From interview-ready business suits to wedding guest attire, we carry styles that look as good as they feel.

Shirts & Casual

Oxford button-downs, tees, polos, and everything in between—weekend wardrobe staples that actually work together.

Shoes & Boots

Dress shoes, boots, sneakers—you name it. Quality footwear that supports every step of your day.

Accessories

Ties, belts, watches, and small touches that pull an outfit together. The details matter here.

Special Occasions

Weddings, graduations, first communion—whatever the event, we'll help you dress for it right.

Personal Service

Real advice from real people. We take the time to understand what you need and point you in the right direction.

Come Say Hello

Visit us on
High Street.

Send Us a Message

Have a question? Drop us a line and we'll get back to you.

Ready to look your best?

Stop by Jerry Moe's on High Street or give us a call. We'd love to help you find exactly what you need.

Is this your business?This is my business