Categories: Shoes

The search for the perfect modern wingtip – Rockport

The Search for the Perfect Modern Wingtip: Rockport Hillandale – $110.00

It’s no secret that shoes can make or break your look.  Wear a bad pair and everything else will be nullified, no matter how well put together the rest happens to be.  It’s also no secret that a combination of classic details on a modern shape can lead to stylistic victory.  It’s the reason why the Mercedes SLS, the pockets square, and sleek modern laceups with wingtip details have garnered such a fan-base.

For the wingtips to qualify for this search, they’ve got to be sleek in silhouette and not too clunky in the toe.  First up, The Rockport Hillandale Oxford.

The view from above

The Pros

  • Wingtip stitching but perforations limited to the toe
  • Closed lacing keeps the shape clean
  • Great gentle chisel toe
  • Available in wide widths
  • adiPRENE cushioning in the heel

The Cons

  • A little spendy at $110.  But you do get free overnight shipping from Endless
  • That jagged heel.  Pretty distracting.
  • All rubber sole.

The Verdict

A terrific looking shoe from above.  But if that jagged heel is extremely noticeable, that could be a deal breaker for some.  A great option for the 2Eers and a good option for fellas with a normal width foot.  Put a leather sole on the bottom and it’s a steal.
.

Joe

Recent Posts

1 Sale 4 Outfits – Brooks Brothers 25% off + addit. 10% off for members

Stacks on clearance too. 4 style scenarios mined from the BB F&F Sale.

4 hours ago

Style News: Orient is discontinuing the Bambino Automatic OG

A tip of the cap to a real home run of a watch.

5 hours ago

Allen Edmonds Rediscover America Sale 2026 – Top 10 Picks

New releases + timeless icons which rarely go on significant sale. One of their biggest…

2 days ago

Win it: The VAER R1 Oceanracer II Chronograph

USA Assembled. "Speedy" good looks. Sold out, but yours to (possibly) win.

4 days ago

Most Wanted Affordable Style – September 2026

New diver color combos, waxed & quilted jackets, and another alternative to wearing a hoodie.

5 days ago