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A Conversation With Jack Lessing, President
★★★★★ 4.9 · 3,200+ verified reviews

Twelve years in.
Still obsessed
with every stitch.

The first salesperson at B. Draddy — now its President — sat down to talk through his six favorite pieces this season, what's moving in menswear, and the details most brands skip. Watch the interview. Shop the picks.

Free shipping over $200 30-day returns Made to last
New · 6 Chapters
The Interview
with Jack Lessing, President
Official apparel partner of
The Presidents Cup '24 & '26Metropolitan Golf Assn.Golf Assn. of Philadelphia2026 PGA Championship2026 U.S. Open
3,200+
Five-star reviews
12yrs
Building the brand
100+
Top clubs & resorts
1polo
Where it all started
01
Chapter One — The Community

We didn't build a customer list. We built a family.

“The people who wear B. Draddy know each other. They run into each other at the same clubs, the same tournaments, the same weekend trips. That's not a marketing funnel — that's a family.” Jack Lessing, President

When we started, we sent polos to a handful of friends and asked them to be honest. Twelve years later, a lot of those same people are still on the phone with us — sending notes, sending referrals, showing up at events in pieces they bought seasons ago.

It's why we partner with the Presidents Cup, the MGA, and the GAP. The community was already there. We just kept listening.

02
Chapter Two — Jack's Top Picks

The six pieces I'd actually tell my friends to buy.

“I pack these for every trip. Not because I have to — because I want to. If I won't wear it Saturday morning, we don't make it.” Jack Lessing, President

Everyone asks me what to start with. So here's the honest answer — the six pieces that live in my bag, on my hooks, and in my suitcase more than anything else I own.

Start with the polo. You'll understand the rest once you feel it.

The six pieces, ranked

Bestsellers · Verified reviews
The Jack Long-Sleeve Polo
Jack's #1 Pick
No. 01
The Jack Long-Sleeve Polo
Organic Peruvian Pima · 7 colors
$132
★★★★★ 5.0 (15)
Shop the Polo →
The Elliot
No. 02
The Elliot
Scottish cashmere · 6 colors
$670
★★★★★ 0.0 (0)
Shop Quarter-Zip →
The Finnooch Hoodie
No. 03
The Finnooch Hoodie
Italian merino wool · 5 colors
$330
★★★★★ 0.0 (0)
Shop the Layer →
Big Daddy Short
No. 04
Big Daddy Short
Long-staple cotton · 5 colors
$142.00
★★★★★ 5.0 (16)
Shop the Short →
Ambassador Pant
No. 05
Ambassador Pant
4-way stretch · 4 colors
$142.00
★★★★★ 5.0 (11)
Shop the Pant →
BD Premium Cotton Hat
No. 06
BD Premium Cotton Hat
Washed cotton twill · 5 colors
$39
★★★★★ 5.0 (4)
Shop the Hat →
The Fabric

Why it feels the way it feels.

Fabric i.

Organic Peruvian Pima

The cotton 99% of brands can't get their hands on. Longer staple = softer, stronger, and the kind of drape that gets better with every wash. It's the reason our polo has 847 five-star reviews.

Polos · Tees · Shorts
Fabric ii.

Italian Merino Wool

Breathable, temperature-regulating, travel-proof. The Italian mills we work with have been spinning this yarn for generations — and you can feel it. A real layer, not a sweater costume.

Quarter-Zips · Sweaters · Vests
Fabric iii.

Scottish Cashmere

Sourced from one mill in Scotland that's been making cashmere for over a century. Plush, never pilly. You're not paying for the name — you're paying for the five-hour drive to Hawick.

Cashmere Collection
The Full Interview

Six chapters with Jack Lessing.

Sit down with the President of B. Draddy. No scripts — just Jack, the brand he helped build, and twelve years of honest perspective.

Ch. 01 · 1:42

On the B. Draddy community

Ch. 02 · 2:08

Jack'stop picksthis season

Ch. 03 · 1:55

What's moving in

Ch. 04 · 2:21

The brandstory, from polo one

Ch. 05 · 1:36

Inside the embroidery room

Ch. 06 · 1:17

Why the detailsmatter

04
Chapter Four — The Brand

Billy Draddy started with one polo. We're still that obsessed.

“The polo taught us everything. How to source. How to fit. How to finish. Twelve years later, we're applying those lessons to cashmere, outerwear, women's — but the obsession hasn't moved.” Jack Lessing, President

Billy and Chris Draddy — the Brothers Draddy — launched with one product: a cotton polo that did the small things right. Long-staple Peruvian Pima. Chest pocket with a bar tack. Engraved buttons. A shoulder seam that actually sits above your shoulder.

That polo opened doors. Club professionals wore it. Tour players picked it up. Brian Harman won The Open Championship in our apparel. Then it became a collection — sweaters, layers, bottoms, a women's line, and a full apparel partnership with the Presidents Cup in 2024 and 2026.

05
Chapter Five — The Details

The embroidery is where you can tell.

“Most people will never notice. The ones who do — those are our people.” Jack Lessing, President

Our 70,000-square-foot facility decorates every corporate order, every partner crest, every Presidents Cup logo by hand-supervised machine. Not outsourced. Not rushed. Watched.

BD
Compass mark · stitched on chest, hem, and sleeve placement
  • i.

    The thread count matters

    High-density thread so logos sit proud of the fabric — they read at 20 feet and don't flatten after washing.

  • ii.

    Placement is everything

    Three millimeters off and the whole silhouette goes wrong. We digitize every crest for every fabric, separately.

  • iii.

    Speed that respects the craft

    Our 70K-sq-ft Wisconsin facility ships corporate and club orders fast — without the factory shortcuts that show up at the third wash.

  • iv.

    The compass on every piece

    Look for it on the back right hem. Small mark, big meaning — it's how we sign our work.

Need pieces for your club, team, or company?

Custom embroidery. Same craft. White-glove service.

Corporate Orders →
Verified reviews

What the family is saying.

★★★★★ 4.9 out of 5 from 3,200+ reviews
★★★★★
Best polo I own, full stop. Fits like it was tailored, the cotton is ridiculous, and the engraved buttons are the kind of detail you only notice once — but you can't unsee it.
Michael C. Greenwich, CT · Verified buyerThe Jack Polo · Navy
★★★★★
Bought the cashmere quarter-zip on Jack's recommendation and it's become my most-worn piece. Plane, clubhouse, dinner — it handles all of it. Expensive, yes. Worth it, also yes.
David P. Chicago, IL · Verified buyerCashmere Quarter-Zip · Oatmeal
★★★★★
Ordered custom shirts for our member-guest with our club crest. The embroidery is sharper than anything we've ever had, and the turnaround was half what we expected. We're switching our entire program over.
Tom R. Head Pro · Met Area clubCorporate Order · 240 units
Before you buy

The honest answers.

How does B. Draddy fit? +

Our fit is tailored but never tight. If you're between sizes, size down for a trimmer look or stay true for classic. Detailed measurements live on every product page, and every piece is built to hold shape through dozens of washes.

What's your return policy? +

30 days, no questions. If it doesn't fit, doesn't feel right, or just isn't you — ship it back unworn with tags and we'll make it right. First-time exchanges ship free.

Why does it cost what it costs? +

Long-staple Peruvian Pima, Italian merino, and Scottish cashmere aren't cheap — and we don't cut corners on construction. Each piece is built to last years, not seasons.

When will I get it? +

Orders ship within 1–2 business days from our Wisconsin facility. Ground shipping arrives in 3–5 business days. Complimentary on orders $200+.

Do you do custom embroidery for clubs or companies? +

Yes. Our 70,000-sq-ft facility handles custom logos, crests, and corporate orders with industry-leading turnaround. Minimums start at 12 units.

How should I care for it? +

Most pieces are machine-washable cold and line- or flat-dry. Cashmere is hand-wash or dry-clean. Care instructions come on every tag.

Join the family

Come for the polo.
Stay for the people.

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Plus first access to every new drop
Jack's Picks From $42 · Free shipping $200+
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