Rain Gear

Take it from me.  As a backpacker, a frequent traveler and having lived in New York for 4 years I know a thing or two about dressing for the elements.  I will not buy a piece that doesn't give me both function AND fashion.
For instance,  I won't wear something that protects me well but is terrible looking and likewise I won't wear something gorgeous if it doesn't do its job.

 Rainy days are a style opportunity - not an excuse to dress like a slob.  You won't see a New Yorker  in an oversized hoodie and sneakers on a rainy day.  You must have the right gear to stay comfortable and dry on wet days.  Getting quality gear is a wonderful investment. It's the difference between a bad mood and a good one for a lot of people. No one is happy when their feet are cold and wet.  What if you could go anywhere and do anything, even outside when it's absolutely pouring.  You don't have to worry about it, you have the right gear, you'll be comfortable and dry no matter what.  Sounds great doesn't it?

Aside from active wear, everyone should have the basics of rain gear that will get you through a  rainy workday or weekend outing. Below is what you will need.

A trench. I'm a firm believer that every woman should have a chic trench coat that suits her body, her wallet and her style.  Trenches can be found at every price point, though you would be smart to buy the highest quality you can afford).  Second, you'll need rain boots or some type of waterproof shoe (last time I checked, athletic sneakers are anything but waterproof - they are made of mesh!) Finally, you will need a good quality umbrella with which you can brave the wind and rain.

Rain Boots

Consider Temperature: Rain boots are HOT.  I suggest sticking a pair of flats in your bag for when you get inside.  Rain boots are terrible to wear inside all day, they are bulky and make your legs sweat.

Necessity: Only wear your rain boots on a day when it is REALLY raining.  I save mine for hurricane season or for extremely muddy and/or flood situations.  Period.  Otherwise, you'll just look a bit ridiculous.  I never understood the girls who would wear their rain boots all day long just because it looks like it might rain. A nice waterproof pair of shoes is fine for most days.

Color: Please spare yourself and buy rain boots in a subtle color or print.  I personally think a crazy print is too much for girls over 18.  Rain boots look best simple and in a nice subtle color.  Yellow boots are the only exception, I think yellow rain boots are really cute. But not with rubber duckies on them!

There really is a pair for everyone, I have the light grey Hunters on the bottom left.

Umbrellas

Color: As with rain boots, sure a bright color can brighten a rainy day in a really chic way but please keep it simple and leave the monogrammed logos and crazy prints in the store. Even the Burberry print looks dated on an umbrella (you know the one, the brown plaid) there are a GAZILLION copies of the Burberry out there anyway, and who wants to be just one more with a brown plaid umbrella? Not me.  I keep it black, all the time, no matter what but I have seen cute umbrellas done in punchy colors like yellow, purple or green.  And if you want to look cute and girly, then polka dots are OK too.

Quality: Get a quality umbrella.  I always feel bad for the person who rounds the street corner and their umbrella turns inside out.  Attack of the cheap umbrella.  Or the guy who has 2 metals rods sticking out of his umbrella and he's trying desperately to keep his head dry while he almost pokes the eyes out of everyone around him.  Spare yourself and invest in a quality umbrella that will not fail you when you need it most.

Size: Golf umbrellas do not belong on crowded city streets.  They are too big. A golf umbrella creates a path of wreckage as you walk down the street.  It forces people aside into curb puddles and makes them bob and weave around your ridiculously giant umbrella. Don't.  Selfish is never stylish.

Trenches

Silhouette: Trenches are chic, they will always be in style so investing in one is always a good decision if you make sure it is a classic and not too trendy.  It also needs to be age appropriate so you can wear it for 5+ years! Single breasted is always best but wear what is best suited to your frame. I tend to think that double breasted trenches add weight and single breasted streamlines and takes weight away.  If you are pear-shaped then opt for one that has a skirt-like break away from the waist.  An A-line if you will.  This type will be absolutely lovely on you. (In the picture below, the 2 on the right edge are A-line)

Color for a trench is not a great idea.  You will want to be able to wear your trench every single day it is raining.  You don't want to be described as "the girl that always wears that purple coat" or "the girl in the bright yellow trench".  That would be unfortunate.  YOU are the thing that should be noticed, not the coat.  No parts of your outfit should ever overpower you.

Quality: Buy the highest quality you can afford, you will not be sorry if it lasts you years and years.

Length:  I think a good trench should hit the knee or just above.  After all, it is supposed to be protecting you from the elements! What good is a trench if it hits you at the hip and you arrive to work with soaking wet thighs and derriere?  Stupid.  I don't care how cute it is - if it doesn't perform, you will regret your purchase. 

Buttons and belt:  Don't ever do the belt through the loop, simply tie the belt in a knot with the clasp hanging, it's the chicest and simplest way.