# Sperry Topsider Gold Cup A/O Boat Shoes



## Ron_A (Jun 5, 2007)

I just wanted to mention to the group that I recently bought a pair of Sperry "Gold Cup" A/O topsiders, and am very pleased. They were $150 - not cheap, but relatively affordable compared to Quoddy, Rancourt, etc. 

In short, they are head and shoulders above the normal Sperry A/O topsiders (which now are running about $85 a pair, by the way). They simply are a much more substantial shoe, with better cushioning and higher quality construction. The only downside that I can see is that they are deerskin lined, and wear a little warm. As a result, they may be a little hot on really warm summer days. Apart from that, I wholeheartedly recommend them as a superior alternative to the Sperry A/O topsider that is not quite as expensive as Quoddy. Definitely worth checking out.


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## Jovan (Mar 7, 2006)

Thanks for the info. I'll definitely give them a look.


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## Brio1 (May 13, 2010)

Ron_A said:


> I just wanted to mention to the group that I recently bought a pair of Sperry "Gold Cup" A/O topsiders, and am very pleased. They were $150 - not cheap, but relatively affordable compared to Quoddy, Rancourt, etc.
> 
> In short, they are head and shoulders above the normal Sperry A/O topsiders (which now are running about $85 a pair, by the way). They simply are a much more substantial shoe, with better cushioning and higher quality construction. The only downside that I can see is that they are deerskin lined, and wear a little warm. As a result, they may be a little hot on really warm summer days. Apart from that, I wholeheartedly recommend them as a superior alternative to the Sperry A/O topsider that is not quite as expensive as Quoddy. Definitely worth checking out.


I also recently bought a pair in " Brown" for 25% off during the F&F sale at a Sperry Top-Sider company store. However, I'm not sure as yet if they were worth paying double (almost) the price of a pair of A/O's -- only time will tell.

Which color did you buy, Mr. A ?


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## orange fury (Dec 8, 2013)

I've tried on some of the gold cup A/O's, and they were really nice, but the two issues keeping me from making a purchase were the aforementioned "warm wearing" aspect, and paying $150 for something that's ultimately going to get beat up and abused. I wear Sperrys because they're a hard wearing casual shoe, in that price range though I would probably start looking at different loafer options. That's just me though.


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## tigerpac (Jan 23, 2014)

Wonder how they stack up against the likes of Rancourt, which are even more expensive obviously.


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## orange fury (Dec 8, 2013)

tigerpac said:


> Wonder how they stack up against the likes of Rancourt, which are even more expensive obviously.


I went in the fiscally opposite direction, I have a pair of $22 espadrilles in the mail on the way to me from espadrillestrore.com lol


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## tigerpac (Jan 23, 2014)

I just can't get into those espadrilles but I'll be curious as to what you think of them in the flesh. Keep us posted!


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## Tilton (Nov 27, 2011)

The Gold Cups are better than A/Os but, in my experience, they won't last substantially longer. 

I will stand by my previous statement that the Timberland boat shoe in smooth rootbeer is the hardest-wearing and best-looking boat shoe south of Rancourt-range.



Worth noting: the only gold cups I have personally owned were the Gold Cup Billfish, which replaced a pair of regular Billfish. More comfortable and more nicely finished, but not notably more durable.


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## tigerpac (Jan 23, 2014)

^That doesn't look bad at all. Though I find it hard to accept that brand after their boot craze. Illogical yes but still there for me.


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## orange fury (Dec 8, 2013)

tigerpac said:


> ^That doesn't look bad at all. Though I find it hard to accept that brand after their boot craze. Illogical yes but still there for me.


+1, that is a really good looking shoe though, I just wish it didn't have the big logo on it :confused2:

...I know I know, this coming from the guy who wears 90% Ralph Lauren stuff with the pony logo...


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## Tilton (Nov 27, 2011)

tigerpac said:


> ^That doesn't look bad at all. Though I find it hard to accept that brand after their boot craze. Illogical yes but still there for me.


Understandable. I felt the same way until I realized those were the boat shoes my father has worn for decades and I could never find a Sperry A/O (Gold Cup or not) that was juuuust right. They're hands-down better looking than any A/O offering from any line of Sperry, in my mind, and unquestionably more durable and more comfortable. There are a few other converts on here aside from myself.


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## Tilton (Nov 27, 2011)

orange fury said:


> +1, that is a really good looking shoe though, I just wish it didn't have the big logo on it :confused2:
> 
> ...I know I know, this coming from the guy who wears 90% Ralph Lauren stuff with the pony logo...


I wear the pony plenty - including today - without really ever caring too much. The Timberland logo is less intrusive than the contrast-colored Sperry logo on the heel counter (in real life), though. I promise.

EDIT: Just looked - looks like Sperry has changed their design since the last pair I bought - they now have an embossed logo in the same spot and no contrast-colored rubber patch on the heel counter.


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## orange fury (Dec 8, 2013)

Tilton said:


> Understandable. I felt the same way until I realized those were the boat shoes my father has worn for decades and I could never find a Sperry A/O (Gold Cup or not) that was juuuust right. They're hands-down better looking than any A/O offering from any line of Sperry, in my mind, and unquestionably more durable and more comfortable. There are a few other converts on here aside from myself.


Whats the model name/price point/where do you get them? Your advocacy of them is convincing me that I at least need to try on a pair, and I'm a lifelong Sperry owner


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## gamma68 (Mar 24, 2013)

I had the opportunity to compare the AO to the Gold Cup recently at my local Nordstrom. While the Gold Cup pair has better cushioning, I don't think they are twice as good as the AO pair to justify twice the expense. I opted for the AO Topsiders and have been pleased with them. Just my .02.


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## orange fury (Dec 8, 2013)

tigerpac said:


> I just can't get into those espadrilles but I'll be curious as to what you think of them in the flesh. Keep us posted!


Will do, I had some Toms (fake espadrilles) a while back that I couldn't stand (fell apart almost immediately and weren't breathable at all, my feet sweat enough to destroy them within a month or so), but my wife and I each bought a pair of these that- combined -cost less than a pair of Toms do. I'll be interested to see how they perform, they appear to be far more breathable.


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## orange fury (Dec 8, 2013)

gamma68 said:


> I had the opportunity to compare the AO to the Gold Cup recently at my local Nordstrom. While the Gold Cup pair has better cushioning, I don't think they are twice as good as the AO pair to justify twice the expense. I opted for the AO Topsiders and have been pleased with them. Just my .02.


Dont the Gold Cup ones have 18kt gold grommets to resist corrosion? I know there was at least one shoe they offered that had that, but I don't remember if it was only one shoe or the whole line.


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## Tilton (Nov 27, 2011)

https://shop.timberland.com/product/index.jsp?productId=4064137

Better price: https://www.amazon.com/Timberland-M...6&sr=1-4&keywords=timberland+2-eye+boat+shoes

Just be sure you get the tan sole - wears much better and is more comfortable. You can also pretty easily find the Made in USA version as NOS on ebay for $65-90.


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## gamma68 (Mar 24, 2013)

orange fury said:


> Dont the Gold Cup ones have 18kt gold grommets to resist corrosion? I know there was at least one shoe they offered that had that, but I don't remember if it was only one shoe or the whole line.


Yes, I believe the Gold Cup has gold grommets. I'm not terribly worried about corrosion on my AOs. I dunno. I'd rather blow the extra $75 on another item to wear. Just my opinion.


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## orange fury (Dec 8, 2013)

gamma68 said:


> Yes, I believe the Gold Cup has gold grommets. I'm not terribly worried about corrosion on my AOs. I dunno. *I'd rather blow the extra $75 on another item to wear. *Just my opinion.


Agree with this


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## Fading Fast (Aug 22, 2012)

orange fury said:


> I went in the fiscally opposite direction, I have a pair of $22 espadrilles in the mail on the way to me from espadrillestrore.com lol


I, too, would love to hear what you think of them. As opposed to tiger pac, I love espadrilles and am always looking for a good, inexpensive source as they are "disposable" shoes in my mind where I don't mind buying them inexpensively, wearing them for a summer and, then, chucking them. I've been buying Tom's version for the last couple of years.


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## tigerpac (Jan 23, 2014)

I just got a message from mom, "Your Dad really liked your boat shoes [they're actually OSB oxfords] last weekend, where did you get them?"

Can't tell mom I have $300 'boat shoes'.... oh well I guess this solves the mystery of what to buy Dad for Father's day!


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## Fading Fast (Aug 22, 2012)

tigerpac said:


> I just got a message from mom, "Your Dad really liked your boat shoes [they're actually OSB oxfords] last weekend, where did you get them?"
> 
> Can't tell mom I have $300 'boat shoes'.... oh well I guess this solves the mystery of what to buy Dad for Father's day!


She'll be able to back into the price when you get them for your Dad.


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## Brio1 (May 13, 2010)

orange fury said:


> Dont the Gold Cup ones have 18kt gold grommets to resist corrosion? I know there was at least one shoe they offered that had that, but I don't remember if it was only one shoe or the whole line.


But you get 18K Gold * Plated * Eyelets (and Lambskin lining) for an extra sixty-five bucks, gentlemen. :biggrin: I concur with orange fury with regard to their inherent warm-wearing nature and therefore I shall probably reserve mine for evenings drinking gin and tonics at the Yacht Club. :drunken_smilie:


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## tigerpac (Jan 23, 2014)

I'll have to get them shipped to me and then remove any pricing. You're giving her too much credit as to looking it up 

Was thinking of going with Rancourt actually because Dad takes a very wide shoe and they have EE in made-to-order with only a 2-week wait time. Plus, curious to see how they compare with OSB anyway.


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## Brio1 (May 13, 2010)

Tilton said:


> https://shop.timberland.com/product/index.jsp?productId=4064137
> 
> Better price: https://www.amazon.com/Timberland-M...6&sr=1-4&keywords=timberland+2-eye+boat+shoes
> 
> Just be sure you get the tan sole - wears much better and is more comfortable. You can also pretty easily find the Made in USA version as NOS on ebay for $65-90.


Do you happen to know if they are offered at the Timberland outlet in Leesburg, Tilton? Thanks for reminding me that the best pair of boat shoes I've owned were probably a pair of Timberlands purchased about 25 years ago and alas, long gone, that is.


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## Ron_A (Jun 5, 2007)

I bought them in brown (to answer Brio1's question upthread). I don't think they're noticeably more durable than normal topsiders. I guess I was thinking that they are pretty good deal in light of what Quoddy is charging these days (I had a pair of Quoddy boat shoes that I didn't particularly care for, but I have worn my Quoddy canoe mocs into the ground).

As for the Timberland brand, interestingly, I had a nice pair of the lug-soled boat shoes that I bought in the 1980s and had for many years. They made a very high quality product then, and were considered a very trad/conservative brand (this was years before the rappers got into the Timberland stuff).


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## Tilton (Nov 27, 2011)

tigerpac said:


> I just got a message from mom, "Your Dad really liked your boat shoes [they're actually OSB oxfords] last weekend, where did you get them?"
> 
> Can't tell mom I have $300 'boat shoes'.... oh well I guess this solves the mystery of what to buy Dad for Father's day!


Mind posting a pic? I've looked the look of them for a while but I can never seem to find pics of folks wearing them without ridiculous hipster rolled up high water pants. I'm curious if they look more boot-like if the pants actually touch the tops of the shoes.


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## tigerpac (Jan 23, 2014)

These are the Rancourt ones, not quite boat shoes but not boot-like either. I'll try to take a pic of the OSB's I have in action when I get a chance.


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## Brio1 (May 13, 2010)

Tilton said:


> Mind posting a pic? I've looked the look of them for a while but I can never seem to find pics of folks wearing them without ridiculous hipster rolled up high water pants. I'm curious if they look more boot-like if the pants actually touch the tops of the shoes.


Did you see my inquiry (#25), Tilton? Have you come across the Timberlands at their outlet in Leesburg?


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## Tilton (Nov 27, 2011)

Brio1 said:


> Did you see my inquiry (#25), Tilton? Have you come across the Timberlands at their outlet in Leesburg?


Sorry, missed it. I didn't even know they had a Timberland outlet out there. It is probably worth calling about to save you the trip. If they do, post it up because I wouldn't mind grabbing another pair at a good price for whenever mine give up the ghost. 8-10 years from now they're bound to cost more.


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## Brio1 (May 13, 2010)

^
No worries. I will give them a call. There is also a BB and a Polo outlet in the same shopping center (not that there is anything really worth acquiring from said stores). And a VV outlet (if you are so inclined to patronize this store).


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## Tilton (Nov 27, 2011)

Brio1 said:


> ^
> No worries. I will give them a call. There is also a BB and a Polo outlet in the same shopping center (not that there is anything really worth acquiring from said stores). And a VV outlet (if you are so inclined to patronize this store).


Polo outlets, I've learned, are basically all jewel-tone twill button downs and other useless junk and at the same prices that Belk or Macy's asks. I've been to the BB there but never bought anything. The VV outlet is fantastic around the holidays, if that's your thing. I can't say no to $25 polos, but polos, OCBDs, and GTH pants are all they usually have for men. I have deer property in Purcellville so I have ample opportunities to stop by. I have purchased some great (and greatly discounted) Under Armour gear (especially their hunting gear if that's your thing) and Restoration Hardware furniture there, but I typically go there with a purpose and power walk, head-down, straight to my destination so as to avoid the bus loads (literally) of Chinese tourists there.

I now work in RTC instead of DC, so Tyson's is far more accessible than it used to be - only adds eight driving minutes to my commute, thus I rarely find reason to go to the outlets unless driven by a purpose. A sub-$60 pair of Timberland 2-eyes should be purpose enough for anyone.


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## godan (Feb 10, 2010)

The affection for lug sole Timberland boat shoes is shared in this part of the country. Boat shoes in name only, they are hardly aquatic, and too loose on the foot for hiking, but they appear in town and on campus paired with jeans, Pendletons, etc. For those who might be driving by the Sierra Trading Post mothership, it is worth knowing that Timberlands are often available there, deeply discounted.


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## orange fury (Dec 8, 2013)

Brio1 said:


> But you get 18K Gold * Plated * Eyelets (and Lambskin lining) for an extra sixty-five bucks, gentlemen. :biggrin: I concur with orange fury with regard to their inherent warm-wearing nature and therefore I shall probably reserve mine for evenings drinking gin and tonics at the Yacht Club. :drunken_smilie:


Lol.

So THAT's why I've never found a use for them, I don't attend a yacht club! :biggrin: Lol that would be the perfect setting for these though, they're definitely some good-looking shoes.


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## Tilton (Nov 27, 2011)

godan said:


> The affection for lug sole Timberland boat shoes is shared in this part of the country. Boat shoes in name only, they are hardly aquatic, and too loose on the foot for hiking, but they appear in town and on campus paired with jeans, Pendletons, etc. For those who might be driving by the Sierra Trading Post mothership, it is worth knowing that Timberlands are often available there, deeply discounted.


If only I were in Wyoming (for a lot of other reasons than that, too)!


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## hardline_42 (Jan 20, 2010)

I just want to chime in and back up Tilton's claims regarding the Timberland boat shoes. They are the best option in their price range. I have at least four pairs (including the lug sole version) and the smooth root beer with honey sole are my "nice" boat shoes. They're a bit heavier than Sperry A/O's, but in a good way. They're just a more substantial shoe and they last forever. I have other Rancourt handsewn shoes and, while they are definitely head and shoulders above, quality-wise, I see no reason to spend the extra money given the way I treat my Timberland boat shoes (actual boat use, fly fishing in the shallows, mowing the lawn etc.). They live a hard life:










On another note, I have a pair of navy blue, sewn in navy espadrilles from espadrillestore. They're nice, but very simple and rustic. The two shoes are identical, no right or left. It feels a bit weird at first, but the canvas (a nice, medium-weight) molds to your feet and you'll eventually have right and left sides. The shoes are handmade in Spain, rather crudely (IMO) but not poorly, if that makes sense. The sides of the upper are folded under and then stitched to the sole so that all of the excess upper fabric is flapping loosely inside the shoe. It's not terrible, nor is it uncomfortable, just weird. The toe is crocheted nicely with thick cotton floss. The soles are comfortable and have a sort of gum rubber grid over the coiled rope (on the classic model; the traditional model is rope only). I've been wearing them pretty often and even wore them out a time or two with shorts and a polo (though, I don't think I'll be doing it again). They look better than I thought they would and are very comfortable. I'll be getting another pair when these wear out.


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## ricardofrancisco (Jan 1, 2013)

I've always liked the gold cup sperry's but I just felt they were too expensive. Now that there has been some discussion here on Timberland's, I am curious as to how they compare against the normal Sperry's and the Horween Sebago's. I would love to have Rancourt's and I saw a pair at the local Brooks Brothers store but they were campsides and not like your usual boat shoe and the price was a bit too high than what I'd like to pay for casual shoes.


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## RT-Bone (Nov 12, 2013)

I also have a pair of the Gold Cups. Navy/brown. Love 'em.


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## hardline_42 (Jan 20, 2010)

ricardofrancisco said:


> Now that there has been some discussion here on Timberland's, I am curious as to how they compare against the normal Sperry's...


The Timberlands have a bit thicker leather, a padded tongue and a rubber welt blake/rapid stitched to the sole. The Sperry A/O does not.


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## godan (Feb 10, 2010)

Tilton said:


> If only I were in Wyoming (for a lot of other reasons than that, too)!


Just to gloat, the STP mothership is a detour of only three miles from my direct route to and from business interests in Wyoming. Even better, STP is opening a new outlet just down the street from my home - within walking distance, also served by convenient express buses and on the way to a favorite indoor range, bookstore and other places I drive to frequently.


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## orange fury (Dec 8, 2013)

tigerpac said:


> I just can't get into those espadrilles but I'll be curious as to what you think of them in the flesh. Keep us posted!





Fading Fast said:


> I, too, would love to hear what you think of them. As opposed to tiger pac, I love espadrilles and am always looking for a good, inexpensive source as they are "disposable" shoes in my mind where I don't mind buying them inexpensively, wearing them for a summer and, then, chucking them. I've been buying Tom's version for the last couple of years.


my wife and I got our espadrilles in the mail today and they're fantastic for the price (we had a 15% off coupon and free shipping! which brought it under $40 total- 2 pairs for less than 1 pair of Toms). These are far more comfortable than Toms IMHO, the jute footbed and thin canvas make for a much more breathable shoe. They're definitely more "rustic" than Toms (uncut excess fabric on the interior), but I actually like the individuality of it. I'm going to have to exchange mine for a smaller size, but I've already ordered a second pair so they can get her before my exchange does. That's how much I like them.










The reorder of mine was $31 (including $9 shipping) after a 20% discount they're running right now. I can't comment on durability obviously, but at first impression I'm a big fan.


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## ricardofrancisco (Jan 1, 2013)

hardline_42 said:


> The Timberlands have a bit thicker leather, a padded tongue and a rubber welt blake/rapid stitched to the sole. The Sperry A/O does not.


Thanks. The thicker leather makes me think if they're comparable to the Horween Sebagos.


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## sskim3 (Jul 2, 2013)

So I ended up on splurging on Sperry A/O Gold Cup on ruelala for $56 which seems like a solid price.



It isn't the most TRAD but I like them nonetheless. Out of the box, they are surprisingly very comfortable and needs little to no break in. For mine, the leather feels like nubuck so I dont know if that helps with the "no break in process". For the price I spent, I plan to wear the **** out of them the rest of summer. We'll see how well they hold up.


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