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.

by John Liu

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.

A: In order to stand out from the crowd, either dress up or down, but stick with one and do it all the way.  Of course, there is a little bit of wiggle room, but if you want to stand out, just don’t plant yourself right in the middle of the “formality” scale by wearing a structured blazer, dress shirt and dark blue denim.

I think the dress shirt/jeans combo is so popular because guys consider it to be that “in between” look.  They think (incorrectly) that by wearing a button down, they are dressing up, but by wearing jeans, they are also keeping it casual.  Their mistake is thinking that the shirt is the piece of the outfit that defines the formality.  In reality, the pieces of the outfit that define formality are actually the pants and shoes.  You could wear a suit jacket, a dress shirt and a tie, but if you wear shorts, it’s still a casual look.  Or maybe they’re doing it because everyone else is doing it.  Either way, don’t follow their lead. 

As for accessories, the idea here is minimalism: skip the belt.  The pocket square is up to you.  You can wear your watch, but only if it’s subtle. 

If you want to make the look more casual, skip the tie.  Or you can skip the jacket altogether and wear a vest instead—but only if all components of the suit are from the same suit (i.e. don’t wear a medium gray pants and a charcoal vest).  As always, fit is absolutely key.  If your suit doesn’t fit, you’ll look like you’re trying too hard.  Tom Ford (left) does it right, as always.

On the other hand, if you’re going to a place where dancing is central, dress up by dressing down.  I say this more for practicality rather than for style.  Wear jeans, but mix it up by wearing jeans that aren’t blue.  A great pair of gray jeans can go a long way.  Slim chinos, like those by Mason’s (available at Barney’s New York and Douglas Fir), are also a great alternative.  In Milan, you will see men wearing navy chinos instead of jeans. 

Also, don’t be afraid to wear a blazer (roll up the sleeves to casualize it); again, just don’t wear a formal, structured blazer over a button down shirt and blue jeans.  The trend of the moment is a horizontally striped crewneck tee.  The gentleman in the gray jacket (right) has the right idea.

A: Dressing for an engagement party and dressing for a pool party sound like wildly different things, but you can combine pieces from each one in order to create an outfit that works for both. When creating your outfit, your first order of business is to dress for a special occasion.  Even though it’s a pool party, you want to dress in a way that respects the special celebration.  Then, taking into account the climate (sub-tropic) and venue (a pool), you’ll tailor your outfit for fun–and swimming. 

The base of your outfit will be your swimsuit.  Choose a suit worthy of a special occasion–one with special detailing, such as arched cutouts or metal fastenings.  On top of your swimsuit, add a sarong that’s pretty enough to serve as a cocktail dress–and large enough to cover your swimsuit in a sophisticated fashion.  When you’re not swimming, wear a pair of strappy sandals (but carry an extra pair of flip flops in your tote bag). 

Should the party be a more formal affair, we recommend a brightly colored, breezy dress over your swimsuit, paired with a sparkly necklace for an extra dash of formality.

A: We have good news and bad news about your plaid pants.  The good news is that you won’t really have to spend a lot of time putting an outfit together when you wear these pants.  The bad news is that it’s because you won’t have a lot of options.  When pairing shirts with these pants, stick to solid, simple colors.  As always, we would suggest a crisp, white shirt (tucked in).  Shoes should be casual, but don’t wear sneakers with these pants.  Try loafers or Tod’s drivers instead.  Oh, and avoid patterned shirts or jackets, or else you’ll end up looking like an optical illusion. 

Plaid like yours is bold, especially on a dressier piece of clothing.  Last season, Tom Ford had a three-piece plaid suit that was particularly eye catching (shown bottom right).  Then again, is there anything from Tom Ford that isn’t?  He probably could find some way to make what amounts to a Hanes white undershirt fashionable, price it at $400, and it would sell out.