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 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.
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Looks like cheap crap. When you can tell from a picture that the leather is crap, it’s a no go. Not to mention the design is ugly as sin. The Grenson Stanley is an example of a well-executed modern take on the classic brogue design. Or the Savoy by Loake. And while they may cost twice as much up front as this cheap eyesore, they will last five times longer and look ten times better. Some things are worth paying a little extra for in return for much higher quality.
Oy. Chalk OneEye up as not a fan. Allow me to play Devil’s advocate… both of those shoes cost over $250. Can you suggest anything under $200? Also, I gotta be a thumbs down on the Grenson Stanley. They do look like excellent quality shoes, but from the pics (which always can be deceiving) they look a little clunky. Are they a little more slim in the toe in real life? Huge fan of the Savoy by Loake. Partially because they’ve got the slim toe, and if you look at a side by side from the top, they don’t look that different in silhouette/stitching placement from the cheap Rockports. No?
I’m so glad you’re taking this up — I’ve been hunting for a good pare of brown brogues that have a modern silhouette (slim and somewhat elongated, not clunky and stubby). But also something that doesn’t feel like it will go out of style quickly (not a fan of the “burnt toe” look on the Rockport Hillandale, for instance). And of course want to spend under $200, preferably under $150.
Found one on zara.com that’s PERFECT, but you can’t buy it online, and after investigating Zara told me it’s only sold in 2 stores in NYC, nowhere else in the country. Looks fantastic, and it says the sole is half leather half rubber… just wish it could be purchased!
So the search continues…
Well, the Grensons are $209 if you get them from Pediwear (according to today’s exchange rate). And the Loakes are $218. But if the $18 is really a deal breaker, then plenty of good shoes can be found at Herring on sale. For instance, the Herring Richmond (made by Loake) is currently $132 (at least in my size). It will be hard to find a good quality shoe that retails for under $200, but great deals can be found if you’re patient and insist on never paying retail prices.
As another example, I recently purchased a $900 suit for just over $150 after searching for a good three months. Obviously, had I needed the suit immediately, I would have had to either pay more or settle for lower quality, but since I was able to take the time to search for a good deal, I saved $750 on a great suit. Similarly, if you need shoes immediately and can’t spend more than $110 (I’ve been there), the Rockports may do in a pinch and will hold you over until you can buy a good shoe. But if you have the time to search for a deal or save up some money, a good quality shoe is well worth it, and can often be had on sale.
Another thing to remember is that the price of an item shouldn’t be considered at face value. A $300 pair of shoes that lasts you 20 years is a much better deal than a $100 pair of shoes that you need to replace 5 times in those 20 years. The former is indicative of a man who looks for value in what he buys, the latter is called being cheap, but you do pay for it in the long run. There is an upper limit to this notion, of course. I wouldn’t dream of buying a pair of Edward Greens or having a bespoke suit made, but then I’ll likely never have the money or the reason anyway.
Anyway, Grensons do tend to be roomier in the toe box, which is great for my feet, but may not be for everybody. But I certainly wouldn’t call the Stanleys clunky. They’re just substantial enough that they look great with heavier fabrics like jeans or cords, but still sleek enough to wear with a suit. I do think the Loake Savoys look better than the Rockports from above. The Rockports are too long and narrow looking. A shoe should have a shape to it, and the Rockports don’t really have much going on as far as shape. Not to mention the materials. The Loake is all full grain leather, while the Rockports have a cheap-looking corrected grain leather upper and everything else is man-made. Don’t be fooled: with a good quality shoe there should be no need for any “adiPRENE cushioning” or the like. Good shoes are comfortable.
Anyway, I believe I’ve lectured quite long enough. My point is that it is much better to insist on quality at a good price than it is to pay less money up front for something that looks like crap and won’t outlast the weather.
@Adam: Those Zara’s are sweet. @OneEye: I don’t know what I’m doing this weekend. I don’t know if I want to know what shoes I’ll be wearing in the year 2030. Sounds like you’re extremely into shoes (which is terrific… glad to have you aboard). But remember, spending $200 on a pair of shoes just isn’t possible for a lot of guys. Myself included.
Oh, trust me, $200 for shoes is hard to come by for someone currently working in a cafe (damn recession).
I guess there are two types. Those who follow the flow of fashion (which is OK if that’s what you like), and those who don’t care what’s “in” this year/season and go for classic, timeless style. The second type invests in quality pieces that will hold up for a long time and won’t go out of fashion any time soon (and thus won’t need replacing). A pair of wingtips is such an item, as is a quality suit, a classic watch, or a good sports jacket. These items have been staples of mens’ clothing for decades or more, and the styles have changed little in that time. They won’t be going away any time soon. A skinny suit a la Thom Browne, on the other hand, isn’t guaranteed to even be in fashion a year from now.
As another example, the “preppy” look seems to be in fashion currently, and that lends itself to the second type of person I mentioned. But someone who is following preppy fashion for now and will follow whatever comes in fashion next won’t be served well by investing in the classic quality pieces that are the staples of preppy style. Such a person would be better off buying pieces that have the look but not the quality, because they will not be wearing much of that clothing soon anyway. Again, there’s nothing wrong with following fashion, but I guess it’s just a different outlook on how to spend one’s hard-earned money.
@OneEye: I have to respectfully disagree with your oversimplification. There’s more than “two types”. I don’t categorize myself as either of your definitions, and I think that’s reflected here on Dappered. I mix a little of both. The best of both if you will. It ain’t all black and white. Grey. Lots of it. And those Thom Browne suits? Laughable. No way could I take myself seriously in one.
@Adam…I saw those shoes at a ZARA in Santa Monica. They are even more beautiful in real life. I didn’t have the money to get them and haven’t gone back. Its been about 2 months so most likely they sold out. But they look outstanding. Zara makes beautiful shoes on the regular so hopefully they either re-stock this style or make something similar soon. Lets keep our fingers crossed.
@OneEye: Do you know any American sites that carry Loakes? I’m really tempted by them, but of course would need to order a couple pairs to try different sizes, and return the others, Zappos-style. The site you linked to only has free return shipping for UK customers.
Thanks!
@Adam: Links were provided by me on this once since I had to look em’ up anyway… but question still stands for OneEye…
Unfortunately, I don’t know of any such site in the US. That does make it a pain for fitting, but luckily I’ve gotten a good fit the few times I’ve ordered from outside of the country.
By bizarre coincidence, I just found out I’ll be in London in a few days! Won’t have much time, but I can check out Zara and a store that carries the Loakes Savoy. If I decide on the Loakes Savoy I can always order it if the price in the shop isn’t as good as on my-wardrobe.com (incl shipping).
@OneEye: As a shoe enthusiast that I’m guessing is based on the UK, do you have any suggestions for shops to check out the Loakes Savoy?
It’s funny… looking closely at the two shoes, I think Zara may have actually used the Loakes Savoy as their “inspiration” for that shoe… very close resemblance, and given that the lack of IP protection in the fashion industry makes copying fully legal/accepted…
Thanks a lot for your help!
I actually live in the US. I just prefer English shoes. 🙂
I have to say, those shoes from Zara do look quite a lot better than the Rockports. Those would be my choice for an “in a pinch” shoe, and they’d make good knock-around shoes after getting a better pair too.
I’d imagine a suggestion on where to find Loakes in London has been posted on styleforum.net and if not, I’m sure someone would be more than willing to help you with that. There’s a lot of shoe geeks there.
I actually have the wingtips from Zara. I bought them in the early summer for work. They are indeed beautiful! However, they have some pretty major cons:
1. 50% of the outer bottom sole, isn’t actually a sole. It looks like a hard sponge. After but a few days of wearing, they are full of miniature holes. Why? Rocks. They get in them, they usually don’t stay long (only a few steps), but you can feel it a little (not painful). The real annoying part is that every time that happens, which is often, it makes a sound! Like you’re grinding something. If you only plan on wearing that indoors then I guess this won’t be a problem for you, which brings me to my next point.
2. It’s damn slippery in malls. What is the floor usually made of? Ceramic? I’m not sure, but the shinny smooth floors of malls is a danger zone for those shoes. In the beginning, I had to train myself to walk appropriately or else look stupid with a little slide here and there. I never fell, but let’s just say that when you turn corners, and someone surprisingly comes right in front of you and you need to sidestep fast… well, you will look a little bit stupid when one of your foot slips from under you.
3. The shoe takes some breaking in. In the beginning, it hurt like mad since the tongue is so short or hard that it digs into the front of your ankle. I think that lasted a bit less than a month and then I never noticed it again.
Verdict: Amazing look for it’s price. But you’re getting what you paid for it, which is a lot of headaches. This is not quality. Also, make sure to use shoe trees on these babies from day 1.
PS: My first review on something (ever). Hopefully, I did well.
I’m a little late to this party but I have to go with OneEye. The leather looks cheap. By the time you have them re-soled with leather soles and heels you are looking at the same cost as a much better shoe.