As far as what one “should” buy, my answer really depends on a few things, none of which concern what season is currently in store.

I am a firm believer that if one splurges on clothes, one should first splurge on essentials, items that never go out of style.  These pieces should be your first priority: a wool charcoal single breasted suit, a wool navy single breasted suit, a couple pairs of shirts (either solid white or solid light blue), a couple of ties (solids and stripes only for now), one pair of black leather oxford lace-ups, one pair of brown leather oxford lace-ups, a wool overcoat (either in navy or charcoal), and a dress belt (black and brown reversible; keep the egregiousness of the belt buckle to a minimum).  I am also assuming you have a pair of dark navy jeans, with no fade or ridiculous embellishments on the rear pockets, as well as solid navy or charcoal sweaters.

This is the foundation of a well-dressed man’s wardrobe; the colors I pick –navy and charcoal- are the two most versatile.  Notice I did not pick a black suit.  I don’t know when it became acceptable to wear a black suit during the daytime, but it is not “appropriate.” 

If you don’t yet have all of these items, get them.  If you feel like you know about proper fit, from reading posts on this site, or from reading magazines, or from other respected forums (Ask Andy about Clothes is a classic), feel free to shop around.  If you are less-than-confident, go to a respected department store and trust the TAILOR (not necessarily the salesman).  Listen to what he has to say, and follow his advice.  Note that magazines such as GQ and the like often pick up on trends that are not deemed “traditional” fit.

Now, if you DO already have these items, pick up pieces from what I am arbitrarily deeming the second “tier” of the foundation.  These items include classics such as bomber jackets, wool peacoats, scarves, mackintoshes, trench coats, slacks, blazers, and suits in colors not previously mentioned (keep them wool, for now).

If you also have these second tier foundation items in your closet, you can start to find more novelty, trendy items.  Read through the trends highlighted on this site; there are plenty and not worth listing here.

As for what I’ve bought recently, I’m never one to buy and tell (designer wise), but I will say that the items included a navy oilcloth peacoat, a crewneck gray sweater, a wax cotton jacket in a fantastic dark olive, and a navy windbreaker with a vivid red detail.  I also managed to find a great pair of cords on Gilt, as well as some ties.  I think my next purchase will be a toggle coat.

If you really are insistent on brand names, I would suggest buying items that do not have labels or logos showing.  You pay for brand names for fit, details, texture and quality of construction (well, you should anyway), not so you can show people how much you can spend.  I have a pretty firm “no logos” rule.  I would make exceptions for jeans from Dior Homme (the “slash” is a logo of sorts) and items from Martin Margiela (the 4 thread indentations are a clever subtle logo).

As far as my favorite stores, I really don’t want to be a walking advertisement for a designer, so I make a conscious effort to mix it up.  Here’s a few of my favorites: I like Steven Alan for button downs; H&M for novelty trendy items; Gilt.com for anything; Alexander Olch for ties; and James Perse for t-shirts.  Michael Kors (the designer himself) is known for loving peacoats, and it is reflected in the peacoats he sells.

One last word on style: an item isn’t a good deal just because it is on sale.  It’s a good deal if you would have paid more than the price for that item, regardless of what the price is and regardless of whether it is on sale or not.

These sleek canvas shoes remind us that casual footwear can be as sophisticated as its more formal cousins–and tons more fun.  Love, love, love the ever-so-subtle striping and the bright purple shoe soles.  Editor’s Note: Sizing is limited at Oak, since these shoes are selling fast.  But they were fantastic enough that we wanted to feature them anyways.

A: I’m not entirely sure what you mean by “totally awesome.” If you mean “totally awesome fit,” then yes, most good bespoke tailors will fit you a suit that wears better than anything else you have (except for another high quality bespoke suit, of course).

Bespoke is more about personal style and quality than fashion.  Translation: avoid a loud, statement-making suit that may be in fashion right now but will go out tomorrow.  I trust you know how to find a good tailor and how to tell him what you want, so I’ll skip right ahead to the details that are available out there.

The bottom line is that bespoke is expensive.  And that’s kind of the point.  It’s not for everything, and the exorbitant price is largely why it stays that way.  If you’re going to go bespoke, you might as well go all out.  At least, don’t skimp on things to try to save a few dollars here and there.

With bespoke, you can indulge yourself in details ranging from patterned jacket linings to exotic materials.  Duncan Quinn, highly regarded in the bespoke world, for example, offers a suit made out of guanaco.  If you can pull it off, feel free to go bold with pinstripes or checks in whatever color you’d like.  Of course with details like these, you’re talking about a suit ranging well into the thousands (Duncan Quinn starts at $4,000 per suit), perhaps even into the tens of thousands. 

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).

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.

A: It’s hard to go wrong with a suit for any interview, but of course it may be unnecessary given the industry.  Then again, there’s that saying that those who overdress may feel like idiots, but those that underdress are idiots.  Moral of the story?  Wear a (casual) suit.

I really do think that while suits are traditionally a formal look, they can also be made to look very casual.  It’s the little things that matter.  Here’s three ways you can make a suit more casual: no belt, a skinnier tie that’s loosened just a little bit, and no socks.  Oh yeah, cufflinks don’t scream "formal," they scream pretentious—especially for a creative job. Leave them at home.  Skip the contrast collar too; you can wear it when one day you’re on the other side of the interview table.

And suits can still be "edgy" – a suit by Thom Browne takes some real confidence to wear, for example.  I’d be safe (and thifty), though, and avoid the Thom Browne suit, unless you’re going into a really artsy industry (no negative connotation intended).

Sidebar: If you’re trying to get a job on Wall Street, stick to navy or charcoal and a white shirt.  You can’t go wrong with a solid or striped tie, either.  The conservative culture of such firms may cause the interviewer to frown upon anything more.  Besides, you should be more worried about trying to answer questions about WACC and Deferred Tax Liabilities than what you’re wearing.

A: Yes, tweed does seem to be back, but take care in how you wear it.  The tweed jacket can be refreshing and cool, but it needs to be done right.

I think tweed gets a bad rap from old school professors who wear it with patches on the elbows.  It can be worn with style, but I’m a bit more classic than the folks at GQ and Esquire, who seem to be pushing tweed as a trend for Fall.  I tend to think of tweed as “country” wear, where sophisticates sip on cognac and smoke pipe tobacco while wearing a fine tweed jacket.  Maybe that’s just me.

If you want to do tweed in the city at night, you may be able to pull it off with the right fit and complementary clothes.  If I had to make one outfit with a tweed jacket, I would start with a medium to charcoal gray tweed jacket (with a slim silhouette, lapels and no patches, of course).  Under that tweed jacket, wear a sweater or button-down.  And finish the outfit off with a pair of dark denim jeans (navy or black, if you like this Fall’s black jeans trend) or even pinwale cords. 

Whatever you do, keep your outfit simple; you’ll already be attracting attention for wearing tweed.  Let people admire the cut of your jacket—don’t distract them with a complicated pattern.  Oh and contrary to the pictured J Crew example, skip the t-shirt under the tweed blazer look. The wool and the rich tweed texture make this jacket more dressy, and the t-shirt tends to make the look immature, not young. The J Crew guys saved the look by layering the cardigan over the t-shirt.