Cotton Cashmere Campus Stripe Cardigan | $79.50 at J Crew

Glen Madras Shirt | $69.50 at J Crew
If Green’s not your color, do check out the shirt in Navy.

Secret Wash Button Down Shirt in Medium Gingham | $59.50 at J Crew
Feeling adventurous?  Try the gingham shirt in a Pale Pink.

Retro Stripe Knit Tie | $49.50 at J Crew

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.

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.

Sutherland Wool Cashmere Topcoat | $310 (sale) at J Crew

In recent years, one-strap bags (“messenger” bags) have become the craze, if not the cliché.  I can see why: they’re practical, more refined than most backpacks and not unstylish.

Who should wear it: College students, IT guys.
Who shouldn’t wear it: White-collar types (unless you’re traveling).

The briefcase is the most refined “bag” a man can have – and accordingly, it’s usually the most expensive.  A briefcase is a statement that you’ve made something out of your life (career wise at least).  Formal and usually made out of luxe materials such as high-grade leather and precious metals (think 24k gold metal locks), briefcases mean business.  But keep in mind there are two types: soft and hard.  Both are pretty much office standards, but the soft ones are a bit more informal.  Keep your briefcase simple and traditional: get one in black or dark brown.  Skip the high tech ones like the $16,000 carbon fiber piece from Hermes.

Who should wear it: White-collar types.
Who shouldn’t wear it: Anyone that’s not a white-collar type – you’ll come off as pretentious.

I don’t know if there is technically a difference between a duffel and weekend bag, but I tend to think of a weekend bag as a more refined version of the traditional rugged duffel.  Weekend bags are really for those guys in New York who want that 3 day trip to the Hamptons or Maine and need something to put clothes, shoes, bottles of wine, and whatever else you want to put in there.  And that’s the beauty of it; it really is a holdall bag – just throw you’re stuff in there. One of my favorite pictures on The Sartorialist is of Michael Bastian wearing a wrinkled dress shirt, Nantucket reds and loafers, while trying to hail a cab carrying a weekend bag (ok it’s a duffel bag…I guess Mr. Bastian can make even duffels look cool).

The downside of weekend bags is that they are a luxury: you don’t really need them.  As a result, most good ones are expensive.  If you do get a weekend bag, though, pay a little more and get one that’s well made.  I like the motto, “Beat up the pretty things;” it describes exactly how I’d treat a beautiful weekend bag.

Plaid is in.  It was in last Fall, it was in through Winter, it was in this Summer, and its in again this Fall.  I like plaid best when it peeks out from under something muted, like a dark-colored peacoat.  However, this jacket is so handsome that you should show off the plaid.  I love the rustic feel of this jacket, and it goes fantastic with dark denim.  But then again, few things don’t.

Also consider a more subdued plaid on a fantastically cut trench, $250 at Banana Republic.

Last year, the Italian-made Common Projects exploded onto the scene, with its signature….well, lack of signature.  Those shoes, almost always monochromatic in color and sans logo (the individual numbering in gold writing on the outer heel is the closest thing), were a huge hit.  I will suggest those shoes as long as they exist, but if you don’t feel like dropping $200+ for sneakers, these Rod Lavers are a great alternative.  Just as clean and just as white, these low tops are simple and understated.  Haven’t you heard? Minimalism is in.

Also consider Common Projects Sneakers, $278 at South Willard, or white Converse Chuck Taylors, $69 at Zappos.

A few months ago, we spotlighted Engineered Garments and predicted big things from them.  The fashion world has noticed: the label recently won the opportunity to design a small collection for Levi’s.  The collection, which will hit stores in a couple of weeks, reflects their signature style: clothes for the American working man, but with a stylish twist. What I like about this unstructured jacket is that even though it has its fair share of pockets, they are patch pockets.  Patch pockets don’t bulge out like cargo pants pockets, meaning that you can dress this jacket up or down.

Also consider: Cargo jacket | $68 at Gap.

Cords are great as long as they are pinwale.  (A wale is the “thickness” of the cord. We prefer a sleeker and smaller wale.)  Wear them when you want to give your jeans a day off; they are similar to jeans in their feel, look, and formality. 

Also consider cord jeans by Levi’s, Gap, and John Varvatos.  I especially love the Gap ones.

If you’re like me, then you’re always looking the perfect shoe that is somewhere in between sneaker and loafer on the casualness scale.  Bucks?  Yeah, but a bit too much sometimes.  Boots? Sure, but a bit too…urban, sometimes.  Enter TOMS, makers of these fine canvas/leather loafers.  I love these shoes because they’re as comfortable as my bedroom slippers, yet they’re handsome enough to wear when I want that upscale casual feel.  Best of all, they’re pretty affordable. And for every pair you buy, Tom’s donates a pair to charity.

Ok, so $200 (after tax) isn’t exactly cheap for a sweater, but if you caught my comment, you’ll realize that this sweater is probably worth more.

I have long loved the simplicity of a white shirt and solid gray tie.  There’s something about it that’s just so sleek yet elegant.  These wool ties by Michael Kors are exactly what you want; matte and with texture.  Thom Browne says that every day, he wears a grey suit with a white shirt and grey tie.  I can see why.

Also consider this grey wool tie by Thom Browne ($150), from his Black Fleece collection for Brooks Brothers.

Leather jackets are back in, and I for one am glad.  Done right, a leather jacket is versatile enough for both casual and more formal occasions.  And, by “right,” I mean snug and trim, like this one by Gap.  The Italians wear leather jackets the best: fitted like a blazer, with a thin layer underneath.  As with most things in style, it pays to follow their lead.

Also consider: the leather jacket for the guy with the bottomless pit of money, by Julius.

Bonus Picks: Omiru considers many aspects, including price, when suggesting pieces for both men and women.  Lifting that barrier on price for a moment, we want to show you some other great (but pricey) picks for Fall. 

This is not just another rugby shirt.  First, there’s the cotton/wool blend, giving it a luxe feel.  Then, there’s the asymmetrical seam (see it diagonal from the shoulder?).  If you’re looking to splurge on a shirt, this is the one.  It looks fantastic underneath a trim black peacoat and either dark denim or well-cut slate-colored khakis.

Okay, so it’s pretty darned pricey and I’m not going to try to justify the price of the sweater this time.  But you should know that if you get it, you’re getting the best sweater of the season: chunky, comfy and ultra-luxe, with its blend of 40% alpaca and 18% wool. 

If you know me, you’ll know that I’m not a huge fan of L.A. “style” – Details magazine recently declared Los Angeles as the most unstylish city in America.  Despite this title, LA has nurtured a safe haven of style in the form of Ryan Conder’s excellent boutique, South Willard.  Prices are far from bargain basement, but you can always find clothes that will add that extra dash of style to your wardrobe.  I like this plaid piece; it looks great underneath a trim, dark colored peacoat.

I know I’ve suggested this watch before, but I only reiterate my suggestion because I love it.  As far as watches go, it’s relatively inexpensive.  Sure, you’re paying $275, but it looks like you paid $2750 for it.  This watch has earned me many compliments from both friends and coworkers.

To find the right sunglasses for you, start with the shape of your face.  Everyone’s face is unique, but there are a few general shapes into which faces can be categorized.  The basic idea is to get a pair of sunglasses that balances out your face shape; that is, a pair that exemplifies the opposite of your face shape.  Moreover, the edges of the glasses should “frame” your face exactly.  If the outer edge of the lens’ frame is wider or narrower than your face, the glasses don’t fit.  Oh, and always make sure you try on the pair in person before buying them.

(2) Often, like with the classic Wayfarer (probably the most timeless pair out there), you can put in regular lenses and wear your sunglasses as a stylish pair of regular glasses.  Go to your optometrist for more information.

A: One time I was at a fancy restaurant in San Francisco.  It was the kind of place where you have to wear a jacket to get in, and if you show up without one, they give you one from their closet.  I sat down and looked at the menu, which was pretty much completely inaccessible to anyone who’s not a Michelin-rated chef.  Rather than try to decipher it, I asked the waiter as casually as I could, “So how is the steak?”

“Oh, it’s terrible,” he replied.

Now, he was being sarcastic, but I got the point: whatever I ordered, it was going to be great.

If you pick the right restaurant, you don’t have to know anything about food and can rest assured that you’ll get a good meal.  Likewise, if you pick the right tailor, you don’t need to know anything about clothes, and you can rest assured that you’ll get a great suit.

Sure, I could give you a long laundry list of things to look out for.  But if you’re going to the right place, I’m certain that the tailor will be doing these things anyways. My one piece of advice would be to know exactly what you want in terms of color, fabric, and style going in.  The best tailors don’t give their input; rather, they simply do what you want them to do.  Besides, the whole point of bespoke is to make a suit for exactly for you.

If you haven’t gone down the bespoke path before, you likely don’t have a good bespoke tailor you can trust.  So do your homework.  Search online for user reviews of tailors in your city.  The bigger the city you live in, the pickier you can be, of course.  When you find a tailor that gets consistently favorable reviews, go visit the tailor and ask to see his/her work.  See if the tailor will let you talk to some of his/her customers and ask them about their experience.

Also, a “huge premium” can actually be really huge when talking about bespoke.  The Kiton “K50,” aptly named because it takes approximately 50 hours to create, costs $30,000 to $50,000, and is made exclusively by Kiton’s chief tailor who personally measures and fits the client.  If you already knew this and still are willing to pay this kind of premium, try Wilkes Bashford in San Francisco, which measures bespoke Kiton, or Kiton in New York.  If you’re in London, check out Kilgour or any other fine tailor on Saville Row. 

Finally, keep in mind that a true bespoke suit isn’t created overnight.  A bespoke suit will take you a few visits to create.  And a good bespoke tailor will allow you to wear the suit, get it cleaned a few times, and then go back for more tailoring for a perfect fit.

Style Tip 1: For more information on the bespoke process, and what you should expect to do (roughly) with each visit, be sure to read this discussion from Ask Andy About Clothes.