If you live in a climate like mine, you might understand what I'm about to say.
For about 3 weeks in May and another few in the fall, I love to dress. I like wearing ties and cute shoes, accessories even. I carry a bag, even if it's nearly empty. A thin coat allows for trendy layering. I wear suede shoes and take an extra 5 minutes on my hair. You see, the (oh so brief) mid-seasons allow for all of this, encourage it even. Temperate conditions and clear skies mean our shoe-choice can be controversial. What a thrill.
But the rest of the time (when it's either 40°C with 90% humidity, or -40°C with a face-freezing windchill) I phone it in. Who wants to sweat through an outfit in the summer? And when we're strapping a parka over everything between November and April, it just seems pointless. And then there's the occasional melt, when the snow and ice turns into mucky slush, and traversing a sludgy-puddle in your delicate footwear is a total nightmare. It's all too much.
So in the summertime I usually wear simple shorts and a button down and in the winter it's some variation of what you see below. Some revolving combination of Pants-Sweater-Shirt-Boots.
I rotate between colours and textures, keeping it comfortable and simple, no-fuss and classic. As long as everything fits, it doesn't come off looking schlubby, even though it really is. And I should point out, this particular "uniform" is pretty common right now. I'm certainly not blazing any trails in this outfit. This could be called What Men Are Wearing, Winter 2012.
TIPS ON FIT AND TAILORING
I just turned 30 and I'm at a very bizarre stage in my life. Not really a medium, but definitely no longer a small. I made the grave error of trying on an extra-small shirt from my closet and then promptly shredded it with my bare hands. The shame. So, what I mean to say is, it can be tricky to find clothes that fit properly, especially if you're experiencing the sudden and severe collapse of your youthful metabolism.
If you love the pattern/colour of a shirt, but the cut isn't quite right, take it to your tailor. They can make all the necessary adjustments for very little money. In the meantime, wear the shirt under a sweater or jacket to hide the extra fabric. If you're between sizes, go up and have it taken in. Not the other way around.
But where dress shirts can't be stretched-to-fit, shoes can - a half-size or so, depending on their constitution, so make friends with a Shoe Guy, too.
Knitwear cannot be tailored.
Buy pants that fit in the waist. Excess fabric can (usually) be removed at the hips and through the leg. Also, if you love the pattern/colour/fabrication of a pair of pants, but the cut is off (ie. the leg is too wide, or god forbid, boot cut) a tailor can often adjust those, too. Keep your receipt and go have a chat with your alterations person. Much like shopping for meat, a tailor will gladly take a few minutes to determine if your item is alterable.
Do you get lazy like me? Do you have a seasonal uniform?
Skinny Chinos, Topman, The Bay, $57
Cardigan, J. Crew, $118
Socks, J. Crew, $16
Check shirt, J. Crew, $68
Cognac chukkas, Cole Haan, $148
(Images from respective store websites.)
FURTHERMORE, ON STYLE:
A Subtle Recommendation (February 7, 2008)
With My Eyes Closed (February 8, 2010)
Summer Style (February 11, 2011)