Can you say classic…with a twist?  The black strap and silver case are nothing new, but the flags, in place of numbers or roman numerals, are a nice touch.

Oak’s signature is to take a classic and add a twist.  Here, the store brand takes a simple pinstripe shirt and adds a patch pocket with an enclosure.  It’s a great casual buttondown to diversify your wardrobe.  After all, you can’t wear Steven Alan shirts every day.

Plaid is usually done best when it acts as a highlight to an outfit.  This scarf does just that.  Speaking of scarves, I love this statement scarf by Henrik Vibskov too, but it’s somewhat more than $100.

Wool ties were a big Fall/Winter trend this year – and, I should say, they are a cold weather accessory; please don’t wear a wool tie during the summer.  At 2” at the widest point, it’s a little on the skinny side, so I’d suggest it as a night-out-on-the-town item, rather than a workwear piece.  2” too skinny for you?  This 3” pencil striped tie from J Crew is also wool and still looks fantastic.

Guys either love or hate the brilliant color of the Paul Smith stripes.  This card case, however, could appeal to both camps, as the stripes are a highlight, not the centerpiece, of the card holder.  And yeah yeah…it’s over $100.  But just barely.

A: Just as dark colored clothes are more versatile than their light colored counterparts, shoes are also more versatile when they are dark.  Darker shades of brown, for example, work with many more colors than do lighter shades of brown.  Because of this versatility factor, I’d recommend that your shoe wardrobe include a few good pairs of black and darker brown dress shoes in a variety of styles (captoe, bucks, wingtip, etc.) before expanding to lighter colored shoes.  

Even though light brown shoes aren’t super versatile, you still have a few good options.  As you mentioned, light brown shoes complement navy blue nicely.  And they also work with light sandy colored pants.  Beyond that, you may also want to try dark olive green dress pants with your light brown shoes.  Other than these three options, however, it’s going to be tricky.  I’m not saying light brown shoes and other colors can’t work; I’m just saying I haven’t seen it done that well (at least, not yet).

Flannel-lined chino | Was $85, select colors now $49.99 at J. Crew.

Every winter, J. Crew comes out with these flannel-lined chinos, allowing men to stay warm and stay stylish at the same time.  If you live somewhere cold, these are pretty much mandatory, whether or not they’re on sale.

Barbour Putney Jacket | Was $250, now $129 at Barneys.

Simple and understated, a Barbour jacket is a staple of the traditional man’s wardrobe.  Don’t miss the chance to get it at nearly half the price.

Garment Dyed Reverse Seam | Was $178, now $148 at Steven Alan.

Steven Alan has quickly become my default for casual wear.  Their dress shirts are the only ones I’ve seen that look better wrinkled than ironed.  As a result, Steven Alan has that kind of “I don’t care, but I still look good” vibe to all their shirts—the epitome of American style.  Plus, they’re a cinch to pack: literally throw them in your suitcase and then pull them out, wrinkled and ready to wear.

Cotton Shirting Tie | Was $55, now $29 at Steven Alan.

Also from Steven Alan, this plaid tie is more fashionable than stylish.  But fear not, the plaid trend will last past this season.  At 2.5” wide, this plaid tie is fine for the office or a night out on the town.

Want more? Check out these ties (all were $62 each, now $39 apiece), also from Steven Alan.

Biker Jacket | Was $310, now $155 at Oak.

This biker jacket is from Oak, so it’s no surprise that it’s a bit edgier and more urban than most things in your closet.  Traditionally, biker jackets are in leather, but hey, we’re in a recession right now.  Also note the white leopard lining detail.  Eccentric lining is one of those things that drives true Sartorialists crazy; they love it when these kind of details are known only to the wearer.

Plaid Belt | Was $120, now $60 at A.P.C.

For the most part, plaid is best as a layering piece or a detail.  Either way, its best served in moderate doses.  This belt is great, but how long you’re willing to wear plaid when its no longer in style is up to you.

Double Layer Waffle Henley | Was $49.50, now $19.95 at Martin + Osa.

If I had my way, henleys would replace t-shirts as the standard casual guy shirt.  That is, except for the simple white t-shirt.  Nothing beats a simple white T.

UPDATE (12/24):  Ok, now I know what you’re thinking: "148 down from 178 may be 17% off, but it’s still not that cheap."  You’ve got a point.  As Warren Buffet says, "it doesn’t matter if you’re 300 or 325 pounds; you’re still fat!" (it has something to do with investing, I swear).

Enter New York’s Housing Works Thift Shops, a chain of secondhand stores of which profits benefit people with HIV and AIDS. Steven Alan has donated more than 1,000 items from his line and his stock, which is discounted as much as 70%.  The items go on sale on December 27th at 11am, and you can be sure that the store will be packed with thrifty sartorialists, so get there early.

A: I’ll address the “his” part of this question.  The “bad weather shoes” problem is much simpler if you’re not a white collar worker.  Without a doubt, the first pair of bad weather boots I’d recommend are by Quoddy, makers of high quality bad weather shoes.  As you can tell, however, they are for people who experience a few feet of snow in the winter.

Desert boots are another viable option if you live in a place with a less harsh winter.  Clark’s desert boots have always been around, but nowadays you can find stylish desert boots everywhere from J. Crew and the GAP (via Pierre Hardy) to high end retailers like Tom Ford.  The beauty of desert boots is that you can wear them while walking around the city as well; it’s a bit harder to “urbanize” those rugged Quoddy boots.

If you’re a working man, you have it a bit harder.  You have to wear dress shoes to the office, unless you work in a creative industry.  Certainly, you can wear galoshes, but that option is more practical than stylish (even though Esquire endorses it).  If you live in the city, where the streets are a bit more groomed (e.g. less snow on the sidewalks), you can try wearing dress boots, but again, at a formal, conservative type office, I’m not sure that would fly.  If you do decide to wear dress shoes or dress boots, do wear ones with rubber soles.  The snow and slush will wreck havoc on your leather soles.  If you absolutely must wear leather soled dress shoes to the office, do not wear them outside; instead, change into them at the office.

Last words?  Please feel free to beat up your shoes; in fact, I encourage you to wear them in.  A lot.  Tom Ford ran a series of ads a year or so ago in which a man in alligator shoes was walking through the mud.  I love this; “beat up the pretty things,” as they say.  Buy high quality things and wear them out.  This kind of nonchalance is the essence of American style, so embrace it.

A: If you’re reading blogs like this one, then you must be dressing much better than a typical government man in a sack suit, in which case, you’ve already won half the from-work-to-a-night-out battle.

First, if you’re going to more…intellectual…events such as museum exhibit openings or galas, feel free to keep wearing the suit.   Chances are most guys will be wearing one, too (well, at least I would hope they would be).

There are also a few quick things you can do to “casualize” your suit.  Go ahead and loosen your tie to add a nice bit of sprezzaturra to your look.  You could always just lose the tie (and belt, perhaps) altogether.

If a full suit is too formal for you, you could try the dark denim and suit jacket look, with or without the tie.  Make sure you tuck in your shirt though.  Warning: this look is rather cliché, but at least you’ll fit in, right?

If you wear a three-piece suit to work, you can lose the jacket altogether, so you’re just sporting a waistcoat over your shirt and tie. Or, replace the jacket with a sleek, leather bomber jacket, with or without your waistcoat.  Black leather jackets make for very sophisticated, urban nightlife wear, and when they’re done right, you look great.  Switching out your trouser pants for jeans (and keeping the waistcoat) will give you a refreshing take on the dark denim look (and one that I favor at the moment).  You may look like you stepped out of a Spurr catalog, but that’s really a good thing.  Keep the tie in all these outfits.