If you read my recent shoe collection post you know that I like longwings quite a bit. They’re an incredibly versatile shoe style, and over the years I’ve collected four pairs from four prominent brands. Since I know I’m not the only one interested in this style of footwear I thought I’d dive in to the details and compare the various aspects of each one – each have their little nuances that make them unique in their own way.

What Are Longwings?

Longwings – also referred to as longwing bluchers, LWBs, and gunboats – are a traditional American style of shoe that features open lacing and a wingtip that reaches all the way to the back of the heel. Made famous by Florsheim, the longwing is a classic and versatile style that has been popular for decades.

My Collection

From left to right:

Florsheim Imperial (vintage), black pebble grain, 8.5D US, ~$80 used. I bought these on Ebay about a year ago. I’ve always liked the black grain leather look, especially after seeing Thom Browne do it so much. The vintage ones are built like tanks and are still popular on the secondhand market, as seen here.

I bought these on Ebay about a year ago. I’ve always liked the black grain leather look, especially after seeing Thom Browne do it so much. The vintage ones are built like tanks and are still popular on the secondhand market, as seen here. Allen Edmonds MacNeil, brown pebble grain, 97 last, 8.5D US, $425 MSRP. This was my first pair of longwings, and is still the pair I wear the most often. They don’t offer the brown pebble grain version anymore, which is a damn shame.

This was my first pair of longwings, and is still the pair I wear the most often. They don’t offer the brown pebble grain version anymore, which is a damn shame. Grant Stone Longwing, coffee suede, Leo last, 8D US, $330 MSRP. Grant Stone is the youngest company on this list by a wide margin, but their products punch above their weight class.

Grant Stone is the youngest company on this list by a wide margin, but their products punch above their weight class. Alden 29336F, tan calfskin, Barrie last, 8D US, $579 MSRP. The quintessential American footwear brand gets more expensive every year, but it’s hard to argue with how wonderful their products are.

Sizing and Shape

I found all of these shoes to fit as expected. Both the Alden Barrie and Grant Stone Leo lasts fit 1/2 size large, so it is normal to size down. In other words, all four pairs are equivalent to 8.5D US, which is my normal size.

As for shape, the Florsheim and Allen Edmonds pairs both have a somewhat sleek almond toe, while the Alden and Grant Stone pairs are more rounded and bulbous. I find both shapes to be quite versatile, but tend to dress the slimmer ones up more and wear the rounder ones more casually. This is underscored by the fact that the Florshiem and Allen Edmonds pairs are darker, more formal colors, but of course all of these are available in many leather options (except the Florsheims, which aren’t made anymore). From sleekest shape to roundest shape, I would order them as AE > F > A > GS.

Construction and Finishing

All of these shoes are made by great companies, so the overall quality level is very good. The Grant Stones are by far the sturdiest and heaviest – it’s hard to tell how much of this translates into actual strength, but they are quite heavy and stiff. The Florshiem pair has the finest detailing, which is saying something given that they are decades older than the rest. They often have two rows of stitching where the others have only one, and have very clean punching on the brogues. Alden has the best welt, with the highest stitches per inch of the pack. And both the Florsheim and Alden pairs have pinking on the tongue (that zigzag finish), which is a nice touch. The Allen Edmonds pair had the roughest finishing when new (loose threads, rough edges, etc), but this is a very case-by-case issue so it’s difficult to make any strong comparisons there. I would roughly rank these (from best to worst) as F > A > GS > AE, but this is fairly subjective. All of them are made well, Goodyear welted, and will last a good long while.

Material

There’s not much use in comparing the materials on these shoes since all are available in a variety of colors and leathers. My favorite are the pebble grains, but the suede is great too. I find the tan color a bit hard to wear, but it’s great for warmer weather and light-colored chinos.

Medallion

An important characteristic of longwings (and wingtips in general) is the toe medallion – the grouping of punched holes (or brogueing) on the toe of the shoe. Although a small detail, there can be many variations from maker to maker.

With that said, all of these have quite similar medallions. The Grant Stone pair has a more complex pattern, but all of them follow the same basic brogueing shape. I think I like the Allen Edmonds pair best, but there isn’t much of a difference.

Country of Origin and Price

Grant Stone shoes are made in China, while the other three are made in the USA (note: this is not true with the modern-day Florsheims. I’m only referring to these vintage ones). I don’t have any strong allegiance to USA-made goods, but it’s worth noting. This can be seen in the price, where the Grant Stones are notably cheaper than the Allen Edmonds and Aldens. Allen Edmonds and Grant Stone will occasionally have sales, so it can be worth holding out for one of those if you’re patient. Aldens can be found on sale every now and again, but it’s not very predictable.

Conclusion

I really like longwings (obviously), and all of these shoes are a great example of the style. There are definitely differences between each pair, but all are a good buy. I would make sure to pick a material and color that suits your style well, since that will affect how you wear them the most. The last shape is important, too, as that will help the shoes work with the rest of what you’re wearing. The quality doesn’t vary nearly as much as the price does, so the most important thing is to find the style and material that are most interesting to you.