The point of this story is to not only emphasize the importance of first impressions, but also to applaud your taking them so seriously.

That said, you don’t want to seem like you’re trying too hard to impress your girlfriend’s parents either.  Look well dressed but not overdressed; look sophisticated, but not old (yes, you can still look sophisticated and casual at the same time).  And try but make it seem effortless, which, admittedly, can be hard.

Since it is a special occasion, you probably want to dress up a little.  A sweater would look a little stuffy, as would khakis or dress pants if not done right.  I would go with either sporty chinos (flat fronts, unless you’re 35) or dressy jeans (dressy meaning dark with no fade).  For a shirt, you can either wear an oxford (keep it conservative here, stick with white, blue or something with stripes) or a polo underneath a cotton or tweed blazer (wool would seem a little stuffy here).

Try the pictured polo from J. Lindeberg (I have one in burgundy and charcoal and it’s GREAT) with a charcoal cotton blazer over some dark denim and either lowtop white sneakers or brown penny loafers. 

You could also try wearing this rugby shirt from Gap underneath a gray tweed blazer like this beauty from Ralph Lauren over some flat-front, sporty stone khakis and brown penny loafers.

It’s always hard to tell another person what to wear, so maybe the best thing to do is tell you what I would wear if I was visiting my girlfriend’s parents (with the caveat that we probably have different personal styles): gray tweed or cotton blazer over a light blue shirt and maybe a burgundy/gray cardigan over dark denim and simple white sneakers (have you seen those Common Projects lowtops?).

The second most important thing is fit.  Bagginess is for kids.  Wear your pants on your waist, not your hips.  If you have any doubts or questions, visit your tailor.

Still unsure?  I would go so far as to even call the happy couple (or someone else that would know).  I’m sure they wouldn’t mind the question and would probably appreciate your respecting the special nature of the event.

For the most part, it doesn’t matter where the wedding takes place, tropical or not. Wear what you would wear to a normal wedding.  My guess is that “coat and tie” means black tie optional.  What to wear to a black tie optional wedding?  It’s pretty standard: a simple dark colored suit, crisp white shirt and your (tasteful) choice of tie.  Since you’re going to be in a tropical climate, however, lighter colors (e.g. beige, white) are also acceptable.  You could also consider wearing a cream tropical dinner jacket. 

To me, though, it seems a bit “off” to wear a white blazer in the fall and especially in the winter even though white has become a year-round color.  White blazers feel like summer wear; I’m even willing to bet that you can’t find a ready to wear white blazer made in a winter fabric (i.e. a heavier wool) for that reason.  I personally stick to shades of navy and gray for my fall/winter blazers.

If you feel confident and savvy enough to wear the white blazer, be careful not to dress like Don Johnson.  Check out Omiru’s feature on how to not give off the Miami Vice vibe and check the great photo in the comments section.

But first, a note on fit. GQ once said, “bagginess is for little kids.”  They’re right; the most common mistake I see teens people make is how they fit their clothes. Keep in mind fit as you buy new clothes.  A major part of being well dressed is wearing clothes that fit you.

The Graphic T-Shirt   
Is there anything more defining of teen fashion than the graphic tee?  Think about it – when adults want to look younger, what do they do?  They wear a graphic tee underneath their blazer!  Young Hollywood often wears interesting graphic Ts – open up a People magazine and check it out.

Nuts Tee | $15 at Threadless

Button-Down Shirts
Great for a date, dance or just anything you want to dress up a bit, sport shirts also are an important fashion rite of passage from dressing like a teenager to dressing like a man in his early 20s.  Roll up the sleeves to casualize these sport shirts.  Higher end sports shirts can act as dress shirts when you wear a blazer or even a more casual casual suit.  Don’t try wearing it with a tie though – most sport shirts have collars that are too narrow to look good with a tie (or even support it).  A final tip?  Try flannel.  When done well (re: NOT grungy), it is refreshingly stylish. 

Diesel Strude Military Woven | $150 at Urban Outfitters

Hoodies
Have some fun here.  You can wear a plain hoodie, or you can choose one with color or interesting graphics. I personally love hoodies that aren’t particularly thick, but then again I’m from sunny Northern California.

Stock Pinstripe Sweater Hoodie | 59.99 at Urban Outfitters 

Track Jackets
I love the retro coolness of a track jacket.  Get a track jacket in cotton instead of that really athletic looking shiny nylon fabric. 

Converse by John Varvatos Track Jacket | $195 at Urban Outfitters

Jackets
Jackets are another fashion “rite of passage.”  Everyone wears jackets, but while kids wear fleece and nylon jackets, adults will wear jackets in wool and other dressier fabrics.  Find a balance here.  You will eventually want a dressier jacket, but for now, you can stick to sportier or casual ones.  Jackets are an investment, and feel free to splurge on a great one.

Diesel Stitched Jacket | $250 at Neiman Marcus

Belts
Belts should not be used out of necessity–that is, your pants should fit you at the waist already.  Belts are another area where you can have some fun by adding some color.  Save your leather belts for wool pants; they are too formal and will look awkward when combined with, say, a graphic tee. 

Stripe Web Belt | $68 at Brooks Brothers

Jeans
Get jeans with a great fade for everyday casual use and wear them to school.  Get dark denim with no fade for dressier occasions like dates and dances.  Blue is great, but also try grey (or faded black).  Don’t waste your money on anything but straight leg jeans.  A word on pocket design craziness: stick to something simple and classy.  This is one area you DON’T want a lot of crazy colors.    The best (affordable) jeans I have seen, hands down, is the classic 7 For All Mankind New York Rinse.  The picture doesn’t do it justice, seriously.  Simple, dark and cool.

Standard Jean in New York Rinse | $163 at 7 For All Mankind

Cords
A great casual alternative to jeans, cords are at their most versatile when they have a medium wale.  What’s a wale, you ask?  A wale is a measure of the width of the “stripe” on corduroy fabric.  The lower the wale number, the thicker the width.

BDG Bootcut Cord Pant | $49 at Urban Outfitters

Shorts
If there’s one thing to remember about shorts, it’s that they should be above the knee.  This is so important that it bears repeating.  A proper fitting pair of shorts should be above the knee.  Please do your part in ending America’s love affair with oversized shorts by buying shorts that fit – i.e., those that hang above the knee.   When spring comes around, try getting some simple light khaki and brown shorts from Banana Republic.  Forget the cargo pockets.

Sneakers
Here’s a style tip: don’t get your everyday sneakers at Foot Locker.  You’ll end up looking like Jerry Seinfeld (read: awkward).  Get low tops instead of those all-purpose K-Swiss sneakers.  Jack Purcells are always a safe bet too.

A:  Not all cashmere is made equal. Cashmere can come in one, two, or four or more ply.  What’s the best?  Two-ply is preferable to one-ply.  But after two ply, any additional ply increases the weight of the garment but not the quality. 

The best cashmere comes from the long strands of hair on the underbelly of a cashmere goat.  Lesser quality cashmere comes from the goat’s back and legs.  Also of importance is the "hand" of the cashmere–or how it feels.  Look for a silky feel, smooth weave, and great softness. 

For reasonably priced cashmere, try Uniqlo, Land’s End, or Banana Republic.  For high quality, more expensive cashmere, check out Brora, who is known for classic Scottish cashmere with a contemporary twist.

Fun cashmere fact? It takes one goat four years to produce enough wool for one sweater.

Pictured: Cashmere V-Neck Sweater | $178 at Banana Republic.

You can make your blazer less “country club” by changing the buttons from gold to a dark navy blue (if they aren’t already).  Changing buttons is a fairly simple task for a tailor and shouldn’t be too pricey. 
   
As for what to wear with your blue blazer, you can’t go wrong with jeans, as long as they aren’t too similar in color.  You can wear blue, of course, but you can experiment with other colors, such as a darker gray denim.  For more formal occasions, you can still look young in gray pants, such as chinos or flannel trousers. Earthy tones such as brown or olive also work here.  Avoid khakis, which will give your blue blazer an older feel.  As for fit, look for pants that are well fitted and slimmer rather than baggier.

For shirts, a crisp white oxford works well here (when doesn’t it work well?).  You can make the blue blazer more casual by wearing a graphic tee.  For something different, though, try a windowpane plaid or smaller gingham shirt, but don’t get too crazy here.  For those blazers that are dark and inky (the ones I like), a skinny-but-not-too-skinny tie looks great here especially in a dark purpleish/gray. 

Complete the look with brown shoes, a brown belt and even a crisp white pocket square.  You could even get away with wearing white sneakers, but be careful – if they’re too athletic-looking you might give off the Jerry Seinfeld vibe. What to wear?  You can’t go wrong with lowtop Jack Purcells. 

A: 
The technology to create cultured diamonds is pretty advanced–as such, these cultured diamonds are the same as natural diamonds in terms of atomic structure, and visually, you can’t tell the difference between a natural and a synthetic stone.  Of course, these facts aren’t advertised by De Beers. 

That said, how you choose to express your commitment to your fiancee should not be dictated by Madison Avenue–or by the whims of fashion.  A ring can be very beautiful whether it contains natural or cultured stones.  The decision should be guided by (1) your finances, and (2) what you and your significant other find beautiful. 

Perhaps a less expensive ring that allows you to invest in a home sooner suits your needs (as a couple) better.  Or maybe you want to trade natural for cultured in order to purchase a larger stone.  Remember the old adage that beauty is in the eye of the beholder.  An earnest heart is the best gift of all.

Photo Credit: Stephend9.

A:  How sweet of your sister to buy you such a useful wardrobe staple!

To make the sports jacket more age appropriate, pair it with a casual top.  The graphic tee plus sports jacket is one of the oldest looks in the book, but there’s a reason why it’s a classic.  For a look that’s a little more "street," you can wear a hoodie with the sports jacket and tee.  To kick the style quotient up a notch, pair it with a deep-buttoned henley or a light weight v-neck sweater.

What colors to wear with brown?  Cream, robin’s egg blue, shades of green, and even orange all pair well with brown.

Enjoy your blazer, and do wear it as you take your sister out to dinner when you’re back at home.

Pictured: Herringbone Blazer | $88 at Gap.