AUTUMN STYLE EVENT | Up to 50% Off

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Toby | Men's Leather Ankle Boots with Buckle Strap
Toby | Men's Leather Ankle Boots with Buckle Strap
Toby | Men's Leather Ankle Boots with Buckle Strap
Toby | Men's Leather Ankle Boots with Buckle Strap
Toby | Men's Leather Ankle Boots with Buckle Strap
Toby | Men's Leather Ankle Boots with Buckle Strap
Crafted by Daniel & Michael
Trusted by 52,000+ American Gentlemen

Toby | Men's Leather Ankle Boots with Buckle Strap

Sale price$64.95 Regular price$129.95
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Shipped by Wed 24 December
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UPDATE: Limited Stock Alert! 5 pieces available due to high demand during the SALE. If you can still click "Add to Cart," it is still available.

Rugged Character, Crafted Detail

Step into heritage style with these distressed leather boots, built for durability and timeless appeal. The open lacing, metallic eyelets, and ankle buckle strap add functional character, while the stacked heel and visible stitching highlight quality craftsmanship. Perfect for casual looks that demand authentic edge.

Built for Lasting Style

  • Distressed leather construction: Natural material with worn-in finish for authentic vintage character.

  • Open lacing with metallic eyelets: Provides secure fit with coordinating laces for classic styling.

  • Ankle buckle strap detail: Adjustable strap at padded collar adds functional rugged appeal.

  • Stacked heel block: Low profile with rounded toe and visible stitching for crafted durability.

Worn by 48,000+ Gentleman Across the United States

Michael

Timeless Smart Casual Style

A clean and polished look with classic appeal. The crisp button-down shirt pairs effortlessly with tailored trousers, creating a refined and balanced outfit. Simple, confident, and well put together.
Michael
Marcus T.

Refined Everyday Design

The jacket features a structured collar, front button closure, and defined seam detailing across the upper section. Its straight cut and flap pocket accents create a clean outline that pairs evenly with tailored trousers.
Marcus T.
Nathan R.

Bold Coordinated Streetwear Look

A bold streetwear look with strong coordination. The jacket stands out, and the matching pants and sneakers create a clean, cohesive style. Modern and confident overall.
Nathan R.
Michael D.

Clean and Structured

The shirt features a structured collar and short sleeves with a consistent check pattern across the fabric. Its straight cut and buttoned front create a clean outline that pairs evenly with tailored trousers.
Michael D.
Robert H.

Classic Casual Street Style

A clean everyday look with a sporty touch. The striped rugby shirt adds structure, while the light denim and sneakers keep it relaxed and balanced. Simple, youthful, and easy to wear.
Robert H.
Daniel K.

Modern Minimalist Smart Look

A clean and structured outfit with a sharp silhouette. The striped blazer adds subtle detail, while the simple top and dark trousers keep the look balanced and refined. Sleek and contemporary overall.
Daniel K.
Adrian L.

Structured and Modern

The jacket features a structured collar with a front zipper closure and defined seam detailing across the upper section. Its straight cut and streamlined design create a balanced outline that pairs evenly with tailored trousers.
Adrian L.
Ethan M.

Clean All-Black Minimal Look

A simple and streamlined outfit with a sharp monochrome finish. The relaxed top pairs smoothly with the wide-leg trousers, creating a balanced and modern silhouette. Understated and effortlessly put together.
Ethan M.

Where It Began

Gentlemen Prime Boston began in 2013 with a simple idea between two friends, Daniel Verne and Michael Loyd. We believed a man’s wardrobe should reflect who he is becoming steady, intentional, and confident in his path.

What started as a small selection we personally chose slowly became a place men trusted when they wanted pieces selected with purpose.

Brotherhood

Recently, our story took an unexpected turn. Michael suffered a serious accident that left him severely injured and now relying on a wheelchair.

Keeping the store running suddenly became much harder than we ever imagined.

To help us continue forward, we introduced our AUTUMN STYLE EVENT | Up to 50% Off  a temporary event where many pieces are offered at reduced prices until the event ends.

Built for the Man Becoming

Gentlemen Prime Boston was never only about clothing. It was always about the man building his life step by step and choosing pieces he can rely on.

Today, every order means more than ever. When you choose Gentlemen Prime Boston during the Autumn Style Event, you help keep alive the store two friends started in 2013 and the story we are determined to continue.

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CRAFTED THROUGH EXPERIENCE

Each piece is developed with care, precision, and a deep respect for the process. From the first cut to the final stitch, every step is considered. Designed with purpose and built to endure.

In a world driven by mass production, choose something made with meaning

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We are available from Monday to Saturday to answer your questions.
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90-Day Money-Back Guarantee & Hassle Free Returns

We’re confident you’ll love your purchase but if it’s not quite right, you have 90 days to return it for a full refund.
For more details check our Return and Refund Policy.