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Casual Wingtip Boots – Five Plus One

Five Plus One is our weekly series of buyer’s guides. We pick a specific category and dig up five great options along with one that’s a little outside the norm.

The Plain Toe boo is the king of versatilty and always a safe bet. But if you already have a pair of daily drivers and are looking to expand slightly, then a causal pair of wingtips is a great option to add some bootmaking flair to your arsenal. They’re versatile to wear with jeans or chinos, and can make a great choice for some business casual fits if you’re in a pinch. Join us as we explore some of the most compelling casual wingtips on the market today, looking at 5 solid options and a crazy ‘plus one’ to keep interesting.

1) Tricker’s: Stow Boot

Casual-Wingtip-Boots---Five-Plus-One 1) Tricker's: Stow Boot

Tricker’s Stow Boots are some of the most iconic wingtips on the market. Shown here in Navy Chromexcel, the large diameter brogueing and natural storm welt really exemplifies Tricker’s style. Made in England, this pair is finished with a natural leather midsole and outsole, which only makes the natural/navy leather contrast pop even more.

Available for $585 from Division Road.

2) Grenson: Fred V Brogue Boot


Grenson’s Fred V Brogue Boot is another great option if you’re interested in British-made, heavily brogued wingtips. The wedge sole balances out the formal panache of the wing tip upper, meaning these are a shoo-in for casual outfits. Each pair is made in England and adorned with oversized wingtip detail, and a fabric heel pull.

Available for $309 from End.

3) Alden: Greenwich Boot


While Alden has a ton of great leathers, their gorgeously-textured reverse tobacco chamois will always reign supreme for many of us. This leather, when combined with their Greenwich Boot pattern, creates a pair far better than the sum of its parts. Built on Alden’s Barrie last with a commando sole, these wingtips are going to look great whether you’re wearing them with jeans on the streets or with chinos at the office.

Available for $645 from Leffot.

4) Cheaney: Tweed C Boot


Wingtips can be rugged, too, yano! Cheaney’s Tweed C Boot is a prime example of a rugged-leaning wingtip, constructed from full-grain leather and sat upon a full Itshide commando outsole. They’re finished with a burnished toe, fabric pull tab, and the same large diameter brogueing we see from many British bootmakers. While these boots are definitely intended for casual wear, they’d make a great addition to any collection in need of workwear boots.

Available for £425 from Cheaney.

5) Meermin: Country Calf


Meermin’s interpretation of wingtips boots, shown here in their Country Calf leather, are definitely not intended as workwear — but if you find yourself dressing more on the formal side, or at least not trudging through the British countryside, they might be right up your alley. Their finished with studded rubber outsole giving them great traction for city wear and a lot more longevity than traditional, leather soled boots.

Available for $245 from Meermin.

Plus One – Vass: Longwing High Boots


VassLongwing High Boots aren’t like much else on the market. They flaunt a longwing pattern, which you usually only see on more formal close laced boots, and a combination of both smooth and pebble grain leather. They also featured a handwelted Goyser welt, a channeled JR oak tanned outsole, and a pebble grain leather pull tab, all of which come together to form a truly beautiful pair of boots.

Available for $995 from No Man Walks Alone.

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