My New Favorite Shoes from Rockport

rockport chukka bootsI’m not much for fashion and I don’t think I dress particularly stylishly. I’m not quite at the point of ratty t-shirts and flip-flops, though if I lived by the beach that might happen more often than I want to admit. Still, my goal when getting dressed is comfort and if I have to choose between comfort and appearance, well, let’s just say I haven’t graced the cover of any fashion magazines in a while.

And so when I received a new pair of boots from Rockport, the Ledge Hill 2 Chukka Boot in New Caramel color, I was surprised just how much I liked them. Then I tried them on, having owned many pair of Rockport shoes in the past, and was even more surprised at how comfortable they were right out of the box. So much so that I did something that’s typically foolish: I brought them with on a trip to San Francisco without even wearing them for a single day to try and break them in.

A testament to how comfortable they are is that after spending two entire days walking all over San Francisco — see my writeup: Walking Around The City by the Bay — I still really like the Ledge Hill 2 boots and am quite impressed with the feel and the finish of the boots. Better, I received many compliments from people about how attractive they were and how they worked really well with my trademark blue jeans, as you can see in the photo above.

As part of the trip, we had a rare chance to visit Lucasfilm for some Star Wars related events that I can’t talk about on penalty of being kicked out of the Rebel Alliance, but you can see me sporting these shoes in the below pic, as I try to convince the Stormtroopers that these are not the chukka boots they are looking for:

dave taylor star wars storm troopers r2d2

Rockport sent these boots to me as part of the Rockport Challenge — #PoweredByRockport — and I have to say that my “field test” of these new boots worked out splendidly, based on the comments I received, the feedback on Instagram when I posted a photo, and on my own appreciation of the fine balance they achieve between comfort and style.

Here’s the good news that I’ve waited until the end of this post to mention: Rockport’s letting me give away a pair of these stylish boots to one lucky reader. Very nice! To enter, all you have to do is leave a comment here on this blog post listing either a place where they’d work beautifully or a place where they’d be highly, highly inappropriate. That’s it. I’ll email you if you win! Contest ends: 18 March, 2015. Which means, sorry, it’s over for now. And congrats to Diana for winning!

rockport chukka boots

You didn’t win? Or you just want to jump and buy a pair — or some other shoes from Rockport? Awesome. I got you covered there too. Use GOFATHERHOOD20 as a discount code (until Apr 30, 2015) and you can save a cool 20% on any shoes you buy on their site. I know, you can thank me later.

And finally, a disclaimer: I’m a part of the Rockport Inner Circle, so they sent me these boots as part of that program. Nice, eh? Just so you’re aware.

45 comments on “My New Favorite Shoes from Rockport

  1. They would work perfectly for a Dad on the go. From the office to my sons events comfort all day. Now getting the Rockies 1st and 3rd base coaches to wear these during a game would be a great marketing campaign but don’t think he MLB would be very happy.

  2. I would wear my new Rockports with Patty on our honeymoon this summer to Greece where we are doing the Grecian sites and then a tall ship cruise from Athens to Istanbul.

    I will create a My Rockports in Greece Facebook page and my Rockports will post daily selfies from sites they visit with me.


  3. i will wear my new rock ports shoes when I take my 3 kids to the store, the doctors, or anywhere else we can dream up during a day in the life of a SAHD to 3 under 5.

  4. Rockports would work perfectly wearing to work then transitioning to my sons evening activities, than to a much needed date night with my wife.

    I remember seeing my dad wear Rockports all the time as a kid. Wearing them now would be a reminder of how much of an influence by dad is on my life then and now.

  5. I used to be a teacher so I was on my feet all day and they would’ve been perfect then. Now that I am unemployed, I can use a pair to go from interview to interview.

  6. I witnessed those stylish boots from afar at Dad 2.0 and can attest they looked great. I’m always looking for footwear that allows me the flexibility of comfort and style, especially with young kids in tow.

  7. Living in Las Vegas, we get our share of visitors. The first thing they want to do is walk up and down Las Vegas Blvd, the main strip in Sin City. What our guest fail to realize as that while they are in vacation and probably slept in until noon, I have just spent the entire day chasing after 2 year old twins. The last thing on my mind is putting any more miles on my poor feet. These boots would be great for helping my overworked feet keep up with the visiting vacationers.

    I just wouldn’t wear them to bed!

  8. i would love to show these off while teaching my next class of employees. They look like they’d go well with jeans too. I hope I win!

  9. These shoes would be terribly inappropriate for climbing Mt. Everast. Fortunately, that’s not something I’m likely to do.

  10. In Boulder, Colorado, where casual dress rules, these shoes would work at work along with a favorite pair of jeans, leather belt and button down shirt rolled up at the sleeves. These shoes remind me of the hugely popular desert boots from the ’70s that were worn by both sexes.

  11. It would be highly inappropriate for me to wear these nice shoes as we walk along the side of the pool at our Walt Disney World hotel. But I would do it to embarrass my tween. He needs to know I still hold some control over his life, even if it is this way!

  12. Size 10.5 med and they would look great at my favorite winery in Carmel Valley in the sun on the deck with my favorite Pinot and no kids… Lol

  13. These are beautiful shoes! If I won, I would wear them to work in my business casual environment. Coming from a dot com business, I had next to no dressy clothes when I got my job in the health care industry. As it stands now, I only have a pair of black dress shoes. These shoes look like they would be perfect business casual but also very appropriate for the weekend. Thanks for offering this!

  14. I have a burly beard. The kind that makes lesser beards cower in its presence, though it’s friendly and welcoming to all. So, where could I wear these burly, yet stylish boots that would be awesome? Everywhere my beard goes. Rugged, bearded men deserve stylishly rugged boots and these appear to fit the bill. Size 11. Thank you. 😉

  15. They would look awesome with my new casual wardrobe given I’ve lost 50 pounds!!! I love the desert boot look. But I’m also wanting a comfortable boot I can wear all day chasing my daughters around a DC museum or the like. Great giveaway brother. They look great on ya!

  16. I would have my dad wear these! He has no fashion sense so these are a great choice and are pretty much versatile… no more weird stares.

  17. They’re gorgeous! Do they come in women’s sizes? That looks like a put on & wear all day. I’m a jeans kinda person; they’d be perfect.

  18. These look like gorgeous leather. They would gather many compliments when worn to usher at church.

  19. I would love to see Pat in a pair of these rather than his usual everyday shoes. It would definitely be a step in the right direction (no pun intended).

  20. These boots would be highly inappropriate while hunting. Good looks and style take a back seat to warmth and sturdiness while you’re out trying to fill your freezer with organic protein.

  21. Highly inappropriate for dining with the captain on a cruise ship. Very appropriate for any handsome dude to wear about town. I’d give them to my husband, naturally. He could use some new scoots.

  22. These boots would walk me through law school in Minnesota. Not only would I wear them to class every single day, but I would tell all of my classmates how awesome they are. I would shout it from the mountain top and occasionally whisper it in the law library. Unless the shoes squeak or make loud clomping sounds, in which case the library would be an inappropriate place to wear them.

  23. I would wear these boots to work as Ive put a lot of mileage on my previous work shoes and barely (dont) have any traction left on them. I could try wearing them with a speedo and my Boba Fett bathrobe to bed but i have a feeling my wife would make me take them off

  24. CONGRATS TO DIANA THOMPSON! She’s the winner. You’ll be getting an email from me momentarily. And as for the rest of you, sorry, I can’t help you upgrade your footwear this time. 🙂

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