CONVERSE ALL STAR OUTSIDER BOOT

After some recent tempestuous times — and a buy-out from Nike — Converse are still strong style contenders with some fantastic collaborations with the likes of Canada’s D-squared, vintage favourites Woolrich, and the ever-trendy John Varvatos. There have also been some fantastic changes to some classic designs that are well worth a look.
These boots are a throwback to the product that Converse used to make back in 1908. I really like the styling and they work well with a trendier jeans-and-jacket combos, with a more classic-look tweed suit, or with a chinos-based outfit.
They are well made and perfect for that fall stroll in the woods or slushy winter trip into the office.
Outsider boots are available in high-top versions and come in black/milk/green, and beech. Shoes in this collection have a MSRP of $120 and are available nationwide at specialty retailers.
RED WING 877 BOOT

The 877 boot is a signature boot for Red Wing. Featuring russet oil-finished leather and it’s distinctive crepe sole, the 877 was originally made without a heel to aid the balance of steelworkers, working on high beams when building skyscrapers in the 30’s.
To me the 877 is the perfect boot. It’s a classic style icon that has been revisited time and time again; Steven Stills, Neil Young and Eric Clapton considered the 877s their boot of choice. More recently the workers from television’s Lost all sported this classic boot as part of their Dharma Initiative outfit.
The 877 has long been a staple with vintage geeks in London, Paris and Tokyo, and the boot is making a resurgence this side of the pond with J Crew boasting a special edition 877 and Red Wing themselves creating a ‘Lifestyle’ line so that we no longer have to trawl through dusty old hard wear stores to find the right pair.
To me, the 877s are the quintessential travel companion. It can be worn on the work site by and be dusted off and worn with a pair of khakis and a dress shirt to take grandma out for dinner.
These boots are tough and will last you a lifetime if you treat them right. I’ve been wearing them for 11 years, and for 10 of those had the same pair. I wore them on job sites, photo shoots, and they have circumnavigated the globe at least four times. When they started to get a little tight last year I sold them on eBay — for a profit. You can’t ask for more than that from a trusty pair of boots.
SEBAGO DOCKSIDE BOAT SHOE

Sebago’s ‘Dockside’ is the original boat shoe, and I personally think it’s a fantastic piece of footwear. My current pair are really starting to come into their own, both comfort and style-wise, and I’ve had them since 2004, though I loved them from day one.
These shoes really are a must-have. There are now a lot of boat shoes on the market from various companies, but in my book none come close to the style or quality of the Dockside.
They are also incredibly versatile, look-wise. They can be worn with shorts and a tee, beaten up old jeans and an old sweater, chinos and a blazer, even a summer suit.
One word though, by them now and start wearing them in for next year. These shoes are as hard-wearing as work boots.