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Wingtip Boot Search: The Sebago Hamilton

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Sebago Hamilton Drysides $99.00 $115.50icon* ($175)

Like a great Summer Suit, there’s something about a pair of sturdy and versatile wingtip boots in the fall. Most have character to burn, and they can be dressed up with many of the rough textures we’ll see once the weather turns cooler. Our search for the best affordable wingtip boots is on, and feel free to send in suggestions via styleip.

*The extra 30% off shows up in your cart.  Sale ends Tues. 10/18 at NOON Eastern.  Use code LCCDAY50 for free shipping.  Thanks to Molokoveck for pointing these out in the comments over here.

UPDATE:  Looks like Lastcall.com is yanking all of us around.  They’re now running a 40% off one item sale and the Sebagos seem to apply.  Looks like this offer ends on the 20th.  Sorry guys, had no idea they’d knock another 10% off.

These have to be the best looking waterproof boots on the market.  They’re part of Sebago’s Drysides collection, so the leather is treated and they’ll supposedly keep your feet dry (within reason, so don’t go swimming in them) right out of the box.

You do gain some shine and lose some suppleness compared to other Sebago leathers, but if you live in a wet climate that’s not bitter cold in winter (sorry Buffalo) these could easily serve as your daily get-to-work-in-the-slop boots.  Put on some merino wool socks and you’re set.  The soles even come with a ready to grip Vibram sole, just like their non-waterproof oxford cousin.

They feel like they might run a tad large, but the lacing system lets you cinch them down good and tight.  Plus, you’ll need that extra room for thick socks right?

The toe shape is perfect.  It’s sleek, rounded, and not too tall or clunky.  They don’t need to be broken in, and the tongue is lightly padded.  Leather quality on the interior seems to be just fine.  Exterior showed up lightly dinged, but nothing terrible.  Good with jeans, chinos, and cords, but not right for flannel trousers and no way with suits.  Available in Black as well through Sebago for the full price of $175.

Best Wingtip Boot under $100 – Hawkings McGill – $88.00  Now available in black, tan, & a brown suede
Best Dressed Up Wingtip Boot – Italian Made Ciro Lendini Wingtip Boot – $149.00


Comments

  1. A handsome boot for a handsome price. I am not a wingtip guy, but these could be an exception. Wonder if they would age well?

  3. Sebago is hitting it out of the park with a lot of their stuff. These and the Beacon boot both look awesome.

  5. I wear a 10 1/2.  Would you recommend the 10 or the 11 since they don’t have a half size until past 11?

  7. I’m a 10 in Allen Edmonds. I have a pair of these in size 10 and there’s a little too much room in the toe, though it feels fine once you get it laced up. I say go with the 10.
    Just a word on the leather, as mentioned it looks a little unnatural out of the box, mostly the color looks slightly off at first. Not sure if that’s due to the finishing that makes them waterproof or what.
    I have to say though, as slight creases form in the leather it becomes very evident that the quaity is excellent. It flexes and wrinkles like good quality full-grain leather and not that cheap bonded crap. I think these will look great once they’re a little beat up.
    I also find they keep my feet very warm. I live in Canada and these are going to be my go-to fall/winter boot.

  10. Just pulled the trigger on these. Will have to see once they arrive if they’re as nice as they look online.

  11. Also, when I added them to my cart, it was an extra 40% off, making them under $100 before tax. Not bad at all.

  13. These were exactly what I have been waiting to get.  Unfortunately they do not have an 8/8.5 in stock.  Anyone know where I could pick these up elsewhere?  I quick google search did not show up with much.

  15. Am I going to look bad if I wear these with my black leather bomber jacket? Cuz I will probably do it anyway haha.

  20. They do ship to Canada, you just have to order by phone. Same price, and I didn’t get charged duty. I’m not sure if that’s because Sebago is made in the US, but I didn’t think they were.

    With a phone order, my total price was $97 + $5 = $102, but that was during the 40% off plus an additional 15% off sale.

  21. I am pretty sure they allow you to cancel your original order within 24 hours if you call or do the online chat.  I did that a few weeks ago when I ordered a shirt then realized I different one a little later in the day.  Just cancel and re-order

  25. Should be $99 + $5 = $104. I didn’t pay any taxes or duties and only five bucks to get them to my door. I don’t know if customs missed them, but I ALWAYS get dinged with duties and in this case I didn’t.

  28. Ive been wanting a couple pairs of boots lately (John Varvatos, Cole Haan) but with winter coming up in Chicago, these may be just what Im looking for. Waterproof closes the deal as my John Varvatos suede chukkas almost got destroyed last winter.

    Price cant be beat. 1/3 of the cost of other options ive been looking at.

  29. For corrected-grain, waterproof boots these look very good. Especially at this price point – I don’t think that you can do any better. This is a great find, Joe.

  32. I’m not sure, but I believe you have to pay return shipping. It may depend on the reason for return. The sales associate I spoke with seemed kinda hazy on the details

  33. Just ordered them for a total of $106. I really hope I won’t get any taxes or duties (I live in Quebec, so it may be different. I hope they fit too.

  37. I’m not gonna lie, my bank account does a little happy dance every time Dappered featured an item and it isn’t in stock in my size.

  39. Size 10 is back! Just ordered mine; hope it ends up being worth it, checking back at 4:20am…

  40. Not anymore! But luckily I snatched a pair of the 10s this morning before they re-sold out.. after them un-selling out. <.<  For anyone still interested there are both sizes 7 & 11 still up for grabs.

  41. I just grabbed a pair of size 11s, tried to get them shipped to Canada over the phone, apparently they aren’t shipping these boots outside of the US.

  42. Score! I needed new waterproof boots and these look amazing, and for $99 holy crap! 
    Thanks Joe!!

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  47. After looking at the Florsheim boots in this column, a pair of Marlton oxford shoes caught my eye. I ordered black but a pair of dark, dark Navy were delivered.   I am considering keeping the shoes – they look great, but I don’t know what I colors pair best.   Do navy shoes pair with grey, brown or black slacks?

  48. A tip for anyone who may have waited too long for their size — I needed a 9 1/2 and got on their live chat with customer support and they were able to find some in a store and have it delivered to me (discount code still applies). So, all hope is not lost!

  53. Got my 11.5s in the mail (I wear a 12 dress shoe and these seem to fit well). Anyone else concerned about the thin soles on these? Seems like they will wear out pretty fast. Thoughts?

  55. To those who bought them, how are they holding up? I’ve had them for a day and I find the leather on the dark brown version weirdly colored and textured — does it get better with use?

  57. Not silly.  I think it depends but the vast majority of the time they won’t be dressy enough.  If it’s some thicker tweed or maybe a corduroy suit, and the weather is crap, then I say go for it.  But that grippy sole makes them pretty casual.  So for a standard business suit it’s best to stick with dress shoes or more dressed up boots…

  58. DO NOT BUY THESE BOOTS! I bought these a while back based on this review. This turns out to be the worst pair of boots I have ever owned. Parts of the boot feel stiff and plasticky; while the other parts are dull and do not hold a shine. In addition, the boots do not breath at all while somehow not able to keep out any water. My feet are always wet, either from sweat or from water that seep through the sole. Utterly devoid of any redeeming quality.