Loake Pimlico vs. Red Wing Beckman 9016

[acinod]

I've been searching for some time for the most versatile shoe outside of a full suit. It needed to have the following properties:

• Able to be worn with raw denim, khaki chinos and grey flannel trousers
• Able to be worn comfortably on rainy days
• My go to travel shoe - need to be able to walk in them for the whole day
• Elegant and beautiful
• Under $350

Initially, I was drawn towards RMW's Comfort Craftsman. It fulfilled all the above properties but when I finally tried them on, I just didn't like the look. The lack of lacing and detail made the shoe look quite odd. So chelsea boots are out of the question. I also tried on some CDB which have been highly recommended here but the crepe sole meant I couldn't wear them in the rain. The Bushacre's sole works around this but I don't like the look of it.
I have narrowed my options down to the following:
Loake Pimlico in Dark Brown Suede
The Loake Pimlico are quite beautiful and elegant. The Dainite sole allows it to work in foul weather yet being comfortable to wear. There is a leather version but I prefer suede due to its more casual nature and the soft texture it provides. I also like the capital last (I have the Aldwych) so I prefer the Pimlico over the Kempton (another Loake chukka with different last).
Red Wing Beckman 9016 in Cigar Featherstone
The Red Wing Beckman 9016 I'm sure is more well-known here. They take a while to break-in but I heard they will become incredibly comfortable in the long run. The rugged nature of the boot allows me to be more careless with it and the cigar featherstone leather is also of amazing quality. I also like the soft black laces which contrast very nice with the cigar colour.
Although I love both boots, unfortunately I can only choose one.
LOOK: The Pimlico has a much more elegant toe shape and the soft texture of the suede looks so beautiful. Though in some photos, I am drawn to the rich colour of the featherstone leather in the Beckmans. Personally I think the Pimlico look better.
VERSATILITY: I own 3 pairs of pants: N&F Weird Guys, Epaulet Khaki Chinos and Epaulet Oxford Grey Flannel. Both the Pimlico and Beckman pair very nicely with all these pants. They are also versatile for all dress occassions except for business formal. Although I think the Pimlico may be a bit more versatile due to its darker colour and will be more appropriate for the dressier side of business casual.
FUNCTION: Ultimately, no matter how nice or versatile a shoe is, it is useless if it cannot fulfill its function. I plan to travel to NYC/Chicago this Christmas and I will be taking one of these boots with me. It will take me from the airport to the hotel and for many miles of walking/shopping/sightseeing in a NYC/Chicago winter. The main concern with the Pimlico is that I'm not sure how the suede will fare against the rain/snow that I might encounter. I've worn suede before but I live in Australia and our winters are mild at best. I've had conflicting opinions on suede in rain but I am not afraid to take care of them. The Beckmans' seem like a better choice against foul weather but I'm worried they won't be comfortable in time for my trip next month. I heard the break-in period can take from a few weeks to several months!
So Loake Pimlico or Red Wing Beckman 9016?

 

[JayH]

I have a pair of the Loake Pimlico. I mainly use them for casual wear - selvedge rolled up ankle freezers also rolled down and dressier. They go great with trousers as well. I have worn them in more formal situations, navy and charcoal suits.

No problems with the Dianite sole, although i haven't jumped in puddles, there is no problem for all season use.

They seem a little roomier than other shoes on the capital last, probably because i have skinny ankles, but nothing significant. Keep in mind they are a DARK brown.

 

[acinod]

I have a pair of the Loake Pimlico. I mainly use them for casual wear - selvedge rolled up ankle freezers also rolled down and dressier. They go great with trousers as well. I have worn them in more formal situations, navy and charcoal suits.

No problems with the Dianite sole, although i haven't jumped in puddles, there is no problem for all season use.

They seem a little roomier than other shoes on the capital last, probably because i have skinny ankles, but nothing significant. Keep in mind they are a DARK brown.

Thanks for sharing your experience, luckily my ankles aren't that skinny.

I see you live in Sydney as well so if you're like me the only time we see snow is up in the mountains. I do want to take this shoe to get me through my US Winter holiday but just a bit worried about the snow over there. Probably need some spray protector?

 

[umbrella613]

Funny, I was looking for a pair of shoes with your exact specifications - versatility, quality, and price. I tried a pair of Red Wing Beckman chukkas. Sizing was strange - they ran quite narrow, and even after going up half a size I had to return them (fantastic return policy, btw).

Eventually got this - http://www.johnstonmurphy.com/product.aspx?c=1332&sc=1332&pid=98288 . J&M has greatly improved/expanded their styles, and I think their quality is OK for the price.

My little story. Would have loved to get a pair of Loakes but am not a fan of buying before trying (no stores in NYC!).

 

[Spark]

This is a no brainer: Loake all the way.

I have the Kemptons in suede and they are incredibly versatile. I wear them with jeans, chinos, dress slacks and they would not look out of place with a suit. They are the first shoes I generally reach for when traveling as they can be dressed up/down and require only a quick brushing for maintenance. Danite sole is both comfy, weatherproof, durable and not overly bulky. No matter what anyone says, rain/wet weather doesn't bother suede - just treat them when you get them and then 1x a year thereafter.

I'm not so sure I'd buy a leather pair of Loakes - even the 1880s I've seen can't hold a candle to benchgrade CJs - but the suede is fine and wears surprisingly well

The Red Wings are a different animal and I'm not sure how you managed to make them a finalist considering your criteria. "Elegant and beautiful" are perhaps the two last words I would choose to describe them or probably any other RW product. Much more streetwear oriented and limited in range compared to the chukkas.

Regarding fit, look at Pediwear's site - they have an excellent guide to all of the Loake lasts and I'm sure a few emails with them can get your size dialed in.