A: GQ hit on the 5 most important things a short man should look for in a suit:
(1) Buy Short Length Suits
(2) Wear your pant legs with very little break.
(3) Visually lengthen your arms by showing a little bit of your shirt cuff.
(4) Peak lapels help to visually elongate your body, making you look taller.
(5) Look for suits with a low stance (the place where the two front pieces of the jacket meet). 

Beyond this, be sure to check out the different “How to Buy a Suit” guides by magazines such as GQ and Esquire, and men.style.com.  GQ recently had a feature of “best suits under $500.”  Esquire has an article on the best suits under $500, $1000 and $2000.  GQ also has a general how to buy a suit guide that I highly recommend.

Now there are plenty of guys that wear $500 suits that look $2000 and plenty of guys that wear $2000 suits that look $500. The trick to making any suit look good (even one that is $500) is tailoring and fit.  As for where to go to find this perfect fit, here’s where I would recommend starting your search. 

$250 and below: H&M (really)
$250-$500: J. Crew, Banana Republic,
$500 - $1000: Hugo Boss (I personally love the fit, but we have different body types)
$1000 - $3000: Neiman Marcus, Saks, or Bergdorf (if you are in New York).   Personally, I have found Paul Smith London to be the best fitting designer time and time again, but again my body type is different than yours (6 feet, 185lbs). 
$3000+: Go bespoke…but I don’t recommend your first suit being bespoke.

A: You’re off to a good start with the dark wash denim trouser jeans.  They’ll make you look long and lean, and they’re versatile enough to be paired with almost everything. 

So as not to look like the "ugly American," I would evoke the look of Clemence Poesy, a French starlet whom you may have seen in recent movies like Harry Potter and In Bruges.  If that’s not enough, she’s also the new face of Chloe perfume.  So as to affect Clemence’s impeccably French style, keep you clothes simple and clean–but with a twist. 

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.

A: Sounds like you’re already on the right track.  Since you’re curvy and have a full bust, you want to keep your neckline very open by wearing single breasted jackets in semi-fitted shapes.  Like you already know, jackets with a single or double button closure are going to be your best bets.  (Bonus points for jackets that button right under your bustline.)

And cheers for you for embracing the White Jacket.  White jackets and blazers look fresh for summer, especially given this season’s focus on white.  But how do you wear these white jackets without looking like an extra on Grey’s Anatomy?  Here’s three ways to avoid the doctor look with a white jacket:

A: First of all, your wife is right.  Even when she is wrong, she is right.

Secondly, in this case, she really is right.  Jeans and a well cut jacket looks awkward; it’s something about the formality of a well cut blazer and the casualness of jeans that causes this clash.  Just because every other guy wears a blazer and jeans doesn’t make it right.  You can do better.

If you can’t get the matching linen pants, that doesn’t mean you should wear jeans.  Instead, try some summer lightweight chinos in an olive or a light khaki color (more slate than beige khaki), as the gentleman shown above does (though don’t follow his lead on the sleeve length.  And, of course, you could try finding some blue pants.  I’ve said it before, but you will see men in Milan wearing blue pants in lieu of blue jeans.  Any of these colors would complement your shoes as well.  The trick is to get a pair with the right cut, so as to not make yourself look like you just finished 18 holes of golf.  Try looking into Mason’s or Save Khaki; they make slim-but-not-too slim trousers in fantastic colors. 

Style Tip?  People often say that certain colors never go well together.  Don’t listen to them.  Certain colors are hard to pull off together, but just about every color combination can be done.  Below, a couple of well-dressed gentlemen show how to do brown/black and brown/gray color combos the right way.

You don’t have to buy a bunch of color all at once.  Building a wardrobe is like breaking in a new pair of heels–it’s best done in small steps.  Add a few pieces a season, and your wardrobe will evolve with your ever changing sense of personal style.

For your classic style, try classics-with-a-twist.  Instead of the plain white sweater, try one in bright yellow (which would be lovely with your menswear slacks).  Or instead of plain flat-front pants, try a pair of navy blue sailor pants (which would look great with your white sweaters).

A: Between Washington DC’s conservative dress code, and the weather, which can be pretty hot and humid, you’ve got to strike a balance between keeping covered and keeping cool.  We recommend traditional suits in lightweight, breathable fabrics like cotton.

To flatter your figure, which is a little top heavy with thinner hips and legs, you’re going to want to create a long, lean line with your torso for balance.  Look for lightweight suits with a soft, natural shoulderline and a high armhole.  The high armhole not only looks cleaner and fits better, but it also helps create the illusion of a longer torso.  A low, single button stance is going to be the most figure flattering for the same reason.

Your thin hips and legs make it easy for you to find flattering trousers and skirts.  Almost any pair of trouser pants will work for your figure.  As for skirts, try a nice pencil skirt that hits at just below the knee.  Not only does it work with Washington DC’s conservative dress code, but it’s also going to be one of the most flattering shapes for you.

As for jewelry, I would keep with the traditional, conservative look with simple pearls or gold bangle bracelet.  Complete your outfit with a comfortable pump in a medium high heel.

A: You’re in luck–you don’t need to spend a lot in order to look more mature.  In fact, you can often replicate a designer look at generic prices.  To me, the spirit of “young but mature” rests in taking staples of a man’s wardrobe and putting a contemporary twist on them.  The most common outfit you will see that captures this spirit is the classic t-shirt under the blazer look.  You may also see some guys pushing up the sleeves on blazers.  As for your specific question…

Pants: Ditch the cargo pants.  Those bulky pockets are just a bit too high school.  Instead, try some well-cut khakis in a lighter color.  They’re worth the investment.  I would look into a designer called Save Khaki; I like their cut and casualness. If you’re in New York, you can go to their boutique; otherwise you can find them at online at Barney’s Co-op, Neiman Marcus or Bergdorf Goodman.  And if its prep you want, look no further than a pair of Nantucket Reds; these classics are the very definition of East coast prep.  You can also try Ralph Lauren or J. Crew, which always has some good chinos (and of course, their classic chambray shirt).  Or, if you want something new, you can explore Gant’s Rugger line.  And while we’re on the subject of pants, don’t be afraid to try jeans that aren’t blue.  Grey jeans look great.
   
Shorts: For those hot days, look into some clean cut Bermuda shorts; they’re like cargo pants without the bulky pockets.  Nantucket Reds can be pretty stylish, as seen on Michael Bastian (pictured top right). Also check out what Banana Republic has to offer.  Style tip?  Properly fitting shorts do not fall below the knee.

Tops: You can stick to polo shirts, but I have a feeling that if you look around, every 3rd guy will be sporting a polo.  How to differentiate yourself from these other guys?  Look for polos that deviate from the common styles and brands.  Try investing in some interesting buttondowns; they’ll come in handy for dates too.  Solids and stripes are always a safe bet, but if you feel like being bold, try some checks or plaid.  Whatever you do, leave the collar down; a polo with a popped color isn’t preppy, it’s pretentious.

Shoes: Don’t bash yourself too hard about wearing slip on Vans; they’re actually coming back in style.  Also, classics such as Jack Purcells probably won’t go out of style any time soon, so don’t worry about wearing sneakers every now and then.  You can find some alternatively preppy shoes without breaking the bank though: try some Sperry Top-Sider or L.L. Bean boat shoes.

Blazers/Suits: Also, now that you’re in college, it’s time to look into blazers and possibly a suit if you don’t have one.  You’ll definitely need a well-cut suit for your job interview, so it’s only a matter of time.  For about $500, you can get some pretty good suits at Banana Republic.

A: Cocoon sweaters and coats, though potentially unflattering, are surprisingly versatile to wear.  The key to wearing them is to balance out the volume of the sweater with a slimmer silhouette on the bottom.  This can be the jeans you described, narrow pants, or a slim-cut dress or skirt.  The beauty of the cocoon sweater is that it’s such a distinctive style that you don’t need to enhance it with much flair.  

One of our favorite ways to wear your cocoon sweater is to pair it with a jewel toned short sleeved dress, black tights, and ballet flats (pictured).  This outfit also has the benefit of being figure flattering–because these clothes are body hugging, you won’t lose your shape in the sweater.  Plus, the black tights keep the line of your look cohesive and clean.

Or for a fun evening look, add colorful elbow length gloves (bonus points for a striking color like french blue) and keep the rest of your outfit very simple.