Feb
Your thoughts on the Urban Outfitters Hawkings McGill wingtip boots? I'm wondering if they'll fall apart really soon. They also seem quite orange. picture on gq: /style/street-style/201112/ben-ferrari-new-york-city-street-style-boots#slide=15
Can’t find these on their site, but I’m guessing they’re probably not Goodyear welted or really the best quality leather you could get. I would rather spend $300+ and get a nice pair of boots that will last me more than a year or two.
Jan
This Fits: Red Wing Boots at J. Crew - 40% off
For those of you looking for some serious boots.
Jan
Do you do anything crazy to your boots to get them winter ready? I snagged a pair of AE Bayfields for a good price. Would a normal conditioning & cream routine do me justice for rain/snow?
I mostly wear my Bean Boots for winter slush and snow.
The one thing you may want to do after wearing them is wash them once in a while with saddle soap to get the salt off of them so it doesn’t ruin the leather.
As for doing more than that, I can’t really say. Obaneuf’s LP gets recommended on forums, but apparently it darkens the leather, too.
Jan
These Bison Boots by Brooks Brothers are on sale right now for $99. That is a screaming deal.
And, unlike a lot of other clearance items, there’s quite a few sizes left. I’m going to stick with my Bean Boots to fight the new snow here in the Windy City, but here’s a fairly affordable alternative.
For those looking for warmer-weather boots, Brooks Brothers also has their canvas chukkas in red, blue and tan on sale, too, for $99.
Dec
I'm trying to find a good quality pair of boots for this winter in Wisconsin. I'm a Texas boy so the best pair of boots I have is a set of cole haan's. I've looked through Alden, JCrew (the chippewas look slick) but am trying to stay under 300$. Any recommendations? Or do your followers have any? I don't want to lose any toes while I'm up there.
Snow, ice and salt are generally going to mess up any “nice” boots you’d buy. Best way to fight back is to get boots that’ll keep your feet dry and are bad enough to take the punishment.
I’ve been a convert to L.L.Bean Boots. Virtually waterproof and the best thing I’ve found for dealing with Midwest winters. Oh, and they’re cheap.
L.L.Bean also has these Katahdid Iron Works boots that look pretty tough when I saw them in stores last year.
Via stylegirlfriend:
I couldn’t survive without my Sorels in winter, and I always get compliments on them to boot (unintentional terrible pun but it stays) sorel.com
Dec
I've had to wear steel-toe boots to work for the past ten years. As of the first of the year, this will no longer be required, but nearly my entire shoe wardrobe consists of Doc Martens. With what would you recommend I start?
First, if you feel like you need to continue wearing steel-toe boots, despite the fact that you no longer are required to do so, then keep your ironfoots around. I’d rather wear those boots than be minus a few toes for the sake of wearing “cooler” boots.
Not sure what your price range is, but if you’re looking for some rugged alternatives in high-quality leathers that are made in the U.S. of A., then take a look at Red Wing Heritage Collection and Alden boots, which will have a more workwear vibe to them. It all depends if you want something more workwear or more formal (like a brogue boot) and how much you’re looking to spend.
Obviously, on the high end you can opt for Horween shell cordovan boots that will last you forever. Lots of places are doing collaborations with Alden to make boots from this kind of leather (Epaulet, Unionmade, etc.).
If your budget is around $500 or lower, then you can probably get any of the Indy boot models from Alden.
Now, if you’re completely saying “I’m never wearing a boot again! I want to wear dress shoes!”, then we’ve got a whole another discussion, which will end with me saying something along the lines of, “Buy a pair of black captoe balmorals, a pair of brown wingtips and maybe a pair of penny loafers, too.”
It really depends what your day-to-day work life is like.
Nov
I got my first ever pair of LL Bean boots after getting advice from you and Tommy, and after reading your guide. I ended up getting the 10" brown/brown unlined version in size 9 (I'm usually a size 10-10.5), which still leaves enough room for thick wool socks when it gets cold. Not having the thinsulate means I can wear it in inclement weather that is not cold. A great buy! Thanks for the help.
No problem. Glad you’re enjoying them.
I’m also a fan of the unlined boots. It does make the more versatile for year-round wear.
Nov
I've been looking for some bean boots for awhile and saw the Lands End footwear sale. Any idea how the LE duck boots compare to the bean boots?
While Lands’ End has a fairly good guarantee on their boots, I can’t imagine they’re as time-tested and of the same quality as the L.L.Bean Boots. Still, I have no first-hand knowledge of the L.E. boots — but I do have a pair of Bean Boots and love them.
For ~$50, that’s not a bad price. Still, I read over the reviews of them on their own site and a few negative reviews kept popping up about not having good waterproofing and them falling apart after a while. Indeed, buyer beware.
Oct
What's a good year-round goto pair of shoes? Or howabout something more focused: what's the goto winter shoe?
For year-round, I’d say a brown pair of wingtips. If they’re blucher style, then they’ll be casual enough to go with denim, while still perfectly fine for going with a suit. I think my wingtips are fairly versatile to wear with almost anything in my wardrobe. Get a pair of overshoes and you’ll be set for light snow and average rain, too.
For winter, I thoroughly suggest not fucking around and getting a pair of L.L.Bean Boots. When it got crappy out, these were my default, go-to shoes. I will note, however, that I kept a pair of “normal” shoes at the office to change into and wore the boots for commuting.
If you want something more classy for winter, a pair of military or brogue boots with a Dainite sole (or lug sole if you feel so inclined for a more rugged look) will do you nicely, like the Charles Tyrwhitt pair I mentioned. I’d also take a look at dieworkwear’s guide to rainy-day boots. Those Brooks Brothers shell cordovan boots are amazing.
Oct
Also, I'm looking for footwear assistance. I spend a lot of time on my bike, and it rains a lot in the winter months here but never too hard and it doesn't snow. What would footwear would you suggest for this situation that still looks good?
My initial thought is a chukka-styled boot with a Dainite sole (Charles Tyrwhitt has one, ROTM shop will have theirs), however, I’m not sure how well that works with cycling. Any cyclists have suggestions (as I am not one)?
ADDING from the crowd:
abearemerges said:
in warm weather, waxed canvas vans are actually pretty solid. No leather-soled shoe can take serious biking. I’m hesitant to advise boots, but i’d say look to more casual boots (slimmed hiking boot sort of things) than, say, chukkas.
thisfits said:
Solid suggestion.
brian-m said:
What do you think of the Lands End Crosby Moc Toe boots for $80 right now?
I think they look fine, but kennyp has a suggestion for how they’d work with a bike:
I would stay away from Moc Toe boots on the bike because they are a bit too chunky if you use toe straps/clips. Surprisingly, I’ve had really good luck with my bean boots on my bike. Those trywhitt boots would work really well too.
Thanks for your input everyone!
Oct
I recently purchased the Charles Tyrwhitt but I have not put them through rain yet. Does the leather repel a bit of rain water or should I apply sno-seal?
That’s kind of up to you. I haven’t put them through a downpour yet.
I traditionally haven’t tried to “waterproof” my boots and my commute is relatively short so it’s not often a problem.
While not waterproof, they do tend to deal with rain well enough. I wouldn’t say it’s “repellent” though.
Oct
Review: Charles Tyrwhitt military captoe boots

Back in July, I bought these military captoe boots from Charles Tyrwhitt on super deep discount ($160), but hadn’t really gotten a chance to break them in and use them enough to feel comfortable reviewing them.
After a series of rainy days a couple of weeks back, I used them quite often and I’d say they’re definitely getting the job done and for the price I have no regrets about the purchase.
The facts on these boots are pretty straightforward: Goodyear welt, Dainite rubber soles, pebble full-grain leather and made in England. Finding shoes for $160 that fit that description isn’t usually easy to do, let alone a pair of boots.
In terms of comfort, it did take quite a few wears to fully break them in. The first time I tried lacing them up all the way to the top and tied them tight around my ankles. Well, my ankles could not bend at all which made walking painful and pretty much impossible. So, I loosened up my lacing at the top and now over time the leather’s broken in to allow for tighter lacing.
The walnut color is definitely a favorite of mine at the moment (currently own five shoes in that color), but the currently available pair is in a much darker brown. It depends on your preference, obviously, but I think either works well with most trousers and jeans.
I have noticed that over time the pebble grain has smoothed a bit along the toes. I’m not sure what this means in terms of the quality of the leather, but it’s something you should know. Also, I’ve yet to give these a polish and see how it reacts with some conditioner, but the leather from the beginning did feel quite stiff and now has begun to wear much easier.
Initially, I’d recommend some slightly thicker socks. I did wear some cotton socks, wool socks and some thick socks with them at various times, and can definitely say thick socks felt better. I have some mildly skinnier feet than the traditional medium “D” widths, but not quite enough to be a “C”, so thicker socks helped in the first few wears before it was broken in. Now, it’s gotten easy enough to wear with thinner socks, but there’s certainly room in the boot for thick wool socks come winter.
My primary reason for purchasing these boots was to deal with the slicker surfaces. They’ve held up well enough in rain and I imagine they’ll do well enough in the winter on ice. While I wouldn’t call them “rugged” in comparison to a pair of L.L.Bean boots, they’re probably going to be just fine for a mild snow, which is fine for my work commute.
In terms of pricing, obviously $160 is a good deal, but right now they’re selling for £179, which is about $280. Sub-$300, I think they’re a pretty good deal, but Charles Tyrwhitt does have a history of reducing prices throughout the season. Frankly, it’s up to you and how badly you need a pair — or if you want to take your chances and see if they have your size once they start hitting clearance prices. Just remember to buy from the U.K. site — not the U.S. site — because the prices are cheaper. Also, you should use the U.K. site and size down a full size from your U.S. size to get the U.K. size that fits. I’m a 10.5D US and got a 9.5F UK. For some dumb reason, their size charts only tell you to size down a half size, which to me seems way off.
For comparison’s sake, I stopped yesterday into the Allen Edmonds store located in downtown Chicago to see how the two’s boots compared. The AEs seemed to have a mildly better leather quality just based on my limited touch and handling of them. I wasn’t so much a fan of the lug sole on the Bayfield boot in comparison to the Dainite sole on the CTs — the profile just seemed off and too rugged.
Bottom line: Definitely get a pair if you can wait until they’re on sale. What price you think they’re worth is going to be fairly subjective, but I’d probably pay upward of $250 for these — especially if you’re looking for a Dainite sole over a leather sole.
+++
badscene replied:
What are your thoughts on the toe-box? It looks a little squared off in the picture.
From above, they don’t strike me as squared off, nor do they feel that way when I wear them.
Sep
Rainwear: What I wear to stay somewhat dry

One of the priorities I set for myself recently over the summer was to get my rainwear squared away. Slowly, I picked up each piece and finally consider that part of my wardrobe complete.
The obvious first step was a coat. I don’t think it particularly matters if you have a trench or “mack” overcoat, but keeping your chest and the upper half of your legs dry is pretty necessary on days when rain decides to be horizontal. I have two raincoats — a the blue trench you see above and another tan “mack”-styled one — that I actually bought dirt cheap at thrift stores. Both are vintage London Fog and from what I’ve read they’re from the era when production was still in the United States and the quality still quite good. You see a ton of these in thrift stores, so they’re not terribly hard to find if you search long enough.
Next up was footwear. I have a pair of L.L.Bean Boots, which are great, but they’re not very dressy. I found dieworkwear’s “rainy-day shoes” article helpful in finding an option within my budget. I got a pair of SWIMS overshoes during the spring Friends & Family sale at Brooks Brothers, knocking down the price from $100 to $75 for days when the rain was lighter. For heavier days, I picked up a pair of Charles Tyrwhitt military captoe boots on deep clearance, which feature Dainite soles. Both have worked out pretty well.
Finally, came the last piece: the umbrella. Again, dieworkwear’s article on umbrellas guided my decision on finding a quality one. I’d considered getting a plaid umbrella from Brooks Brothers, but after handing them in person, I thought it might be a better option to consider saving up for one with a solid-stick handle and shaft. For a while, I was planning on going with one of Howard Yount’s umbrellas, which had some great canopy selections, but then I got a really, really lucky break. I’d loved the Francesco Maglia umbrellas dieworkwear mentioned, but thought they were well beyond my budget. Then I found out that they were not only on sale at a local haberdashery (Shrine), but through a Rue La La “local deal” I could knock off another sizable chunk of the price — putting them on par with the umbrellas at HY. I’ll do a full review in the future, but let me just say that at a discounted price it’s well-worth it and the quality is immediately noticeable.
So, that’s my rainwear solution and I expect it to last quite some time.
Sep
I'm in the market for some rain/snow boots. I live in North central Indiana, where the weather is very similar to Chicago. I'm leaning towards 8" Bean boots. Any suggestions? If I do get Bean boots, would you advise me to get the ones with a lining or not? If so which one (thinsulate, shearling, wool)?
I’m a fan of L.L.Bean Boots, too. I have a pair and they worked wonders last winter. Whether or not you go waxed canvas or leather uppers is to you. I personally went with leather.
For linings, I decided against it. Linings are great for insulation, but so are really thick wool socks (which L.L.Bean also sells). If you go with insulation, just get your regular size. If you decide against it, then size down according to their instructions.
I personally only wore mine for commuting and the occasional shoving of snow, so I was able to get away without lining. If you’ve got a lot of hiking, hunting, walking, etc. planned in them, then maybe the lining wouldn’t be such a terrible idea.
Sep
Really appreciate what you're doing with your blog. I'm probably close to you in age, on a fixed budget, trying to up my solid style game -- sticking with basics, building the wardrobe slowly, etc. I've haven't made any great progress with shoes, though. For the summer I've got boat shoes, but now that fall is here I still have some old half-sneaker, half-something else brown leather Sketchers shoes. Suggestions for casual options? Chukkas? Thanks for your help!
Truthfully, I’m terrible at dressing “casually”, and I also don’t recommend going too “cheap” on shoes. So, that’s a bit of a tough one.
On the low end for chukkas, you could definitely look at Clarks desert boots in the beeswax leather. My roommate has a pair and I think they’d probably do fairly well throughout the fall weather. I’m not going to tell you they’re waterproof or anything, but they’ll be decent in a light rain. For what it’s worth, I wore my sand suede desert boots in an outright downpour this summer and they’re just fine. I stuffed them with newspapers when I got home and let them dry out. Texture’s a bit different, but I’d say they’re a slight bit more comfortable now.
If you’re looking for a pair of higher-quality chukkas, then I’d consider giving Allen Edmonds a look right now. Their “Rediscover America” sale is going on and the Malvern is on sale for $276.25. Depending on your size, you might be able to score them cheaper on eBay.
I’d also give consideration to Charles Tyrwhitt’s chukkas (brown, dark brown, chocolate suede) which come in at $217 before shipping.
Speaking of Charles Tyrwhitt, give a look at their chelsea boots (black, brown). I’ve worn them with denim in the past.
I also think captoe boots look pretty good with denim — heck, any boot generally does. The Allen Edmonds Bayfield is $262.50 at Lands’ End right now (code SAVEFF with PIN 9132). Charles Tyrwhitt military captoe boots can be had for around $250 on eBay. L.L.Bean Signature captoe boots are under $200 and are Goodyear welted. If you’re willing to spend a bit more and are an eBay ninja, I’d look out for Alden Indy boots.
Hope this helps.
