A:  How you dress is critically important to making a great impression. You don’t want to send him the wrong signals about you by how you dress—or how you act, or your date may just think you are looking for something other than a significant other.  How to put your best foot forward every time?  Dress for yourself first and foremost.  Here’s what you need to know:
 
How Much to Reveal:
Women know men like to see a little skin, but how much is too much? You want to show enough to get his mind thinking about what is underneath. But suggesting and showing are two very different things.

How do you balance suggesting and showing off your assets?  Two examples: wear a crisp white button-down shirt by Ralph Lauren and leave the top couple of buttons open to hint at some cleavage. Or try a deep scoop neck top with three quarter sleeves.  The arm-thinning three quarter sleeves balance out the suggestive scoop neckline. 

Dress to reveal your strengths.  What’s your favorite part of your body?  Wear clothes that highlight that.  Are you in love with your long, long legs?  Wear a more revealing skirt to show them off.  Do you have an elegant swanlike neck?  Wear a statement necklace to draw attention to it.
 
What to Wear:
If you’re a dress kind of gal, you’re in luck.  Fashion’s fascination with dresses translates into a wide variety of styles for you to choose from.  For a day date, try a cotton sundress or a silk jersey wrap dress (extra points for bright colors or bold patterns), a statement accessory, and the appropriate outerwear.  For an evening date, venture into cocktail dress territory—or, if the occasion calls for it, slip on an evening gown.
 
What about pants—or is a skirt better?  Either can work, but when in doubt, go with a skirt. Skirts are, by nature, more feminine and their inherent sexiness can unleash your natural confidence.
 
If you’re feeling brave, try an above-the-knee length skirt with a sleeved top.  The more your reveal of your legs, the more you should cover up on top—and vice versa.   If you’re more comfortable with conservative skirts, go for an ankle-length skirt (not one that hits at mid-calf—that length is almost universally unflattering) dressed up with sexy heels.
 
As for footwear, high heels add extra shape to your legs—and they’re a real leg lengthener (especially in styles without an ankle strap).  But if you’re not comfortable in high heels, try a lower heel height or a thicker heel, both of which are easier to walk in.

Lastly, you come to the coat.  If it’s cooler outside, then a snug peacoat or three-quarter length coat is an attractive way to finish off your outfit.  If you’re blessed with warmer weather, then a simple shawl or button up sweater would do the trick nicely.

The next time you’re getting ready for a date, dress for the occasion (no evening gowns at Sunday brunch!), but more importantly, dress to make yourself happy so you’ll make the great impression that will get him asking for that next date.

A: 
Headbands are stylish, easy to wear, and versatile. And the great news is that they’ve been re-embraced recently. No matter how long or short your hair is, there’s a headband out there that’s right for you. How do you know what kind of headband will work for you?  Here’s a good rule of thumb: the shorter your hair is, the thinner the band should probably be.

Headband Types:
Not only can you choose the color of your headband, but you can also choose patterns, materials and widths. A solid colored headband can look proper and polished if worn in a classic or neutral color that shows nicely against the color of your hair. Then again, a solid colored headband can also look trendy and fun if worn in a bright hot pink.

What’s hot right now?  The skinny headband is on the rise—probably to suit the ever-so-popular bob hairstyles.  But choose your headband to flatter your own hair and head. Any width can look nice.

How to Wear a Headband: Three Easy Ways
The easiest way to wear a headband is to just slide it on - it’s even simpler than programming a TiVo! But if you’re short on time and want a different look, you can mix up this simple look by changing your part, or wearing the headband with no part.

My newest favorite way to wear a headband is to pull the top half of my hair up and back into a clip. (I usually leave some shorter layers out to frame my face, using pomade to help define the pieces.) Then I put a headband on. For thinner headbands, wear as is. But the thicker the band is, or for a more dramatic look, I suggest putting your hair up so that it has some height (a light and quick application of both holding gel and hairspray will help) and then putting the headband on so that it’s very low and angled a bit forward.

A:  You should be as formal as your bride.  You said that her dress is a full bridal gown, but it isn’t a “crazy formal or elaborate” gown.  Does this mean the dress isn’t down to the floor?  The length of the dress instantly adds (or subtracts, in the case of a short dress) to the formality of the gown. 

If her dress is knee-length, try a blazer over a button-down shirt with wool trousers with dressier leather loafers.  Warning: I wouldn’t suggest pleated khakis and a navy blazer, unless you’re going for the country club look.  Instead, try a medium or dark gray blazer with a white shirt.  You’ll find that a crisp white shirt will really pop beneath that color blazer. 

If her dress is down to the floor, I would say go with a suit but no tie. The key to this look is the shirt collar.  Get a flimsy collar and it will fall down under your jacket lapel and look sloppy.  Keep the look sharp with a firm collar.  GQ explains how to pull off the look here.

In either case, you’ll be wearing a jacket over a button-down, so tuck in your shirt.

You said you want a “relaxed” suit, but I don’t think you mean that.  Relaxed is a term that describes a loose but not baggy fit.  It’s usually associated with jeans.  If that is what you mean, then I apologize.  In that case, try looking at American made suits.  The so called “sack suits” are usually boxier, looser cuts.  The jacket would follow your silhouette, the trouser will feature a wider leg, and so on. 

It’s up to you, but I personally favor a more slim-fitting suit, especially for a no-tie look.  Try some European designers.  I have a Paul Smith London suit and can personally vouch for its fit.
 
A big factor of formality with suits is color.  The darker the color, the more formal the suit.  I would agree with you and stick with a darker suit here.  Moreover, you’re not wearing a tie, which also makes your look less formal, but if you did, I would tell you to wear a skinny (but not TOO skinny) tie.  I would also tell you not to wear a belt.  A lot of people don’t wear belts nowadays, especially with the “shrunken” suit in fashion.  Going beltless is a sleeker look and tends to add an air of informality. The beltless look has become a fashionable look; GQ’s Style Guy (Glenn O’Brien) has written that he never wears belts with his suits. 

Whatever you do, just remember that sophisticated is clean, simple and tailored.  If your clothes are all of those things, you will shine whatever you wear.  Also, before you buy anything, know how things should fit. Certainly, the tailor will help you when if you get a suit, but you should also know yourself how things should fit.  I liken it to buying a car.  Sure, you can go to the dealer and trust everything they say (and if you go to a respectable dealership they probably are honest), but you still want to have prior knowledge.  I strongly recommend reading Details’ Men’s Style Manual.  It will give you a very good sense on what proper fit means and how to really look chic. 

A: 
It sounds like your company is being unreasonably strict in its dress policy, but perhaps "business casual" has been wrongly interpreted by some of your co-workers.  By deeming that womens’ blouses should have necklines to the collar bone, they are ruling out the risk of any visible cleavage. 

Unfortunately for you, the v-neck is by far the most flattering cut for a large bust.  Furthermore, to find shells or camisoles that reach the collar bone would be very difficult.  You could try crew neck light weight cotton t-shirts as the underpinning and then let the lines of v-neck blouses or sweaters work to your advantage.  However, this is still not a graceful, figure flattering look for you.

Some blouses the have a higher neck but a loose silhouette (like the example below), which would be pretty with a long, dark wide legged pant  for work (and jeans on the weekend). The key here is to balance the proportions of tops to bottoms to create an overall long line.  Finish off the outfit with big earrings or bracelets to help draw the eye away from the bust.

Long story short, you’ll have to submit to crewnecks and boatnecks to comply with company policy, but you can work within these guidelines to create moderately flattering looks.  Final style tip?  To look your best in these cuts, be sure to invest in very good bras.

A:  How ironic, as I read your question, I was having tea with a good friend from Knysna, South Africa.  She had never heard of color restrictions on safari–unless you are on a walking safari (in which case your game lodge should inform you of restrictions). 

To be practical, you may want to wear khaki clothes so as not to show dirt and dust and (should the weather be warmer than expected) to deflect some heat.  If you get cold, as you suggest, you may want to look for darker colors, which will hold in the heat.  

In the cities, my friend said to expect colors similar to those worn in Miami - bright and tropical.  Dress in layers, as the temperatures will vary dramatically throughout the day and evening.  It cools down a lot in the evenings, and FYI a lot of buildings aren’t heated.

As for where to find clothes, Orvis online has great travel clothes.  One last tip?  Remember to bring practical shoes and a hat. 

Create a fresh, young look around the black blazer by pairing it with dark rinse (or grey) jeans.  Add a statement top–such as a striped sweater, a graphic tee, or a brightly colored cami.  Finish off the look by adding a pair of boots and draping a thin scarf around your neck.

As for colors, any and every color goes well with black.  You can try a formal look with a polished white, or you can go bold with metallics or bright colors.  Or keep the look refined with a light grey.

A: 
The ideal shirt length for a guy, whether it’s a button down, a polo, or a t-shirt, is halfway down the zipper (assuming your pants actually fit you). 

If you wear something over the shirt -  a sweater, a vest, a jacket, a blazer – tuck your shirt in, unless it’s a properly fitted t-shirt.

While we’re on the subject of fit, make sure the rest of the shirt fits.  As with jackets, you should fit your shirt based on how it fits on your shoulders.  This is because you can shorten a shirt’s sleeves or length, and you can take it in at the waist, but you can’t change the shoulder (it’s also a comfort thing).  The shoulder seam (the line of the shirt that connects the body of the shirt to the sleeve) should rest in the little gap between that little bump at the end of your collarbone and your arm. 

Style tip: This may all sound a lot, but trust me, if you find a shirt that fits properly in the shoulders, as described above, chances are, the rest will fit accordingly.  The bottom line: focus on the shoulder fit, and you’ll probably be all right.

A:  The good news is that you’re blessed with slender calves.  The bad news is that designers find that more women have oversized (rather than skinny) calves–and your boot selections are limited.

With your slender calves, you’re going to want to look for two things: soft materials and stretchiness (since boots cut in stretchy materials have a narrower cut).  Combined, soft material and stretch should hug even the skinniest of calves.  Start your search with this Donald J Pilner boot, which features soft suede and stretch material.  While it was designed to stretch for oversized calves, it may just fit your legs without stretching.

Worse comes to worse, if you find that the soft, stretchy boots are still oversized for your calves, you can have a shoemaker take them in (or splurge for custom boots).

Though you’re down a pair of black trousers, you’re up a pair of (super) dark grey trousers.  So treat the faded black wide-leg trousers like you would a pair of dark grey pants. 

Dark grey pairs well with all kinds of bright colors.  Crack open any fashion magazine from this season, and you’ll see grey paired with bright blue, grassy green, sunny yellow, or even shades of purple. 

Be bold with your fashion choices, and have fun!

Given that the coat will be paired with long skirts and dresses, look for a long coat.  You can let your skirts and dresses show from under the coat, so long as the overall look is loose.  If you have a highly structured coat, over, say, a pencil skirt, you’re going to want to fully cover the skirt.  But if the shapes of the skirt/dress and coat are less severe, a bit of skirt peeking out never hurt anyone.

Here’s a few affordable coats you may want to start with:
Nick & Mo Audrey Tweed Coat | $98 at Nordstrom
Oversized buttons and a cinched waist give this coat some flair.

London Fog Double Breasted Wool Trench Coat | $188 at Nordstrom
You can’t go wrong with a classic trenchcoat.

Jessica Simpson Platter Collar Coat | $188 at Nordstrom
Love the belt and the oversized collar.

Pictured: MICHAEL Michael Kors Belted Wool Coat | $228 at Nordstrom
The standup collar and the metal dome buttons make this coat quietly dramatic.