Wingtip Chelsea Brogue Boot Black side profile view on white background
Black wingtip Chelsea brogue boot rear heel view showing elastic gusset
Wingtip Chelsea Brogue Boot Black close-up wingtip brogue perforation detail
Black Chelsea brogue boot sole and leather outsole detail
Wingtip Chelsea Brogue Boot Black on-foot lifestyle shot with dark trousers
Black wingtip Chelsea brogue boot on-foot styled view
Wingtip Chelsea Brogue Boot Black on-foot walking lifestyle shot

Wingtip Chelsea Brogue Boot - Black

The Wingtip Chelsea Brogue Boot in Black brings the expressive character of full brogue detailing to the clean, laceless Chelsea silhouette. The W-shaped wingtip perforations create visual depth against the rich black leather, making this a boot with more personality than a plain Chelsea while retaining its everyday wearability. Blake-stitched, slip-on, and built to be resoled — this is a boot for men who want their footwear to do more than just cover their feet.

Key Features

  • Full-grain black leather upper
  • Full wingtip brogue perforations across toe and sides
  • Elastic side gussets — slip-on convenience
  • Blake-stitch construction
  • Fully leather-lined interior
  • Leather outsole — resoleable

Need help finding your size?

Sizing help

You'll see full sizes here only — but the right fit depends on more than length. Spend five minutes measuring, and a fitting expert tells you exactly what to order in this style.

The right size for this style

Every last runs differently. We match your measurements to how this shoe actually fits.

Wide fits & half sizes

Not shown online, but made to order. We'll recommend them if your feet need them.

If it isn't right

Exchanges are free. Returns accepted with a small restocking fee. We'll guide you to the correct fit — and keep your size on file for next time.

Find my size Real measurements, matched by a person — not a chart.

Complete the look

The matching belt is cut from the same leather

Cut from the same premium calfskin as your shoes. A matched leather set - from waist to sole.

Belt size — select one

Order the same size as your trousers.

Please select a size before adding.

View details
Flat Belt- Black

Flat Belt- Black

Black Wingtip Chelsea Brogue Boots, Slip-On Character

Built on Blake-stitched construction with a soft leather lining, this boot combines the slip-on Chelsea silhouette — elastic side gussets, no lacing — with full brogue perforation detailing across a W-shaped wingtip toe.

Black leather for men who dress with intention; brogue detailing reads smart casual rather than strictly business formal, so a plain leather Chelsea boot suits the most formal offices better.

Every pair is handcrafted with hand-finished edges, water-repellent enough for autumn and winter wear with a leather spray and reasonable care in wet conditions.

Pairs well with a matching Black belt from our Belt Shop — see the pairing guide above to match your shoe color to a belt shade.

Pairs with dark jeans, slim chinos, charcoal trousers, and smart casual jackets.