the five rules of style

The sun is finally out and after the “longest winter in the history of the world,” I am ready to do some shopping.

In an effort to define my “look” for the season, I examined the trends online and in several fashion magazines (Vogue, Vogue UK, Marie Clare, Elle, Lucky, etc.) and here is a quick shortlist of what is “in” for spring:

Pleats. Structure. Pastels. Primaries. Color Blocking. Stripes. Solids. Florals (Florals? For spring? Groundbreaking.) Urban Athletic. Preppy. Bohemian. Leather. Lace.

spring looks from celine, balenciaga, christopher kane. images via vogue uk feburary issue

Confused?  Seems like anything goes, right?  Not exactly, but it does mean that anything you want to wear goes, IF you follow a few simple rules.

Here are my five rules stylish women follow regardless of trend, season or circumstance.

style rule #1:  great skin, not makeup.

I am not sure who all the magazines and blogs are talking to when it comes to makeup trends, but based on my observations, stylish women don’t really concern themselves with makeup.

Yes, we may adopt a brighter lip or try a heavier brow, but we spend our money on skin care.  Dermatologists, aestheticians, and the women who sell us our skin care (shout out to Anne and Colleen at Erno Lazlo) – this is where we spend our money.  When your skin looks great, you can throw on powder, mascara, and carmex and get on with your day.

bette davis | image via time & life

style rule #2:  proportion matters.

I am not sure why proportion is such difficult concept to master, but it has two basic premises.

The first rule of proportion is the balance of body vs. fabric.

Let’s break down an outfit.  Varsity jacket, white tee, boyfriend jeans.  Basic enough right?  But think about the shape.  One big potato sack.

So to combat that potato sack, you need to wear a shoe with a little heel and your hair away from your face or piled on your head.  The height of the shoe and the exposure of your face elongate the look, balance out the potato bag shape, and remind others that you have a feminine body underneath that potato sack…and probably a pretty attractive one if you are confident enough to rock such a shapeless outfit.

master of proportion: givenchy 1950s  |  image via time & life
master of proportion: givenchy 1950s | image via time & life

The second rule of proportion also applies to what I call the Either/Or.

You can show your arms or your legs, not both unless you are under 21 or it is over 100 degrees.  You can show deep cleavage and even your back at the same time, you must cover your legs to at least the knee. You can wear an extremely short skirt and high heels, but you need to have sleeves on the top or you look like a working girl. Either/Or, get it?  Outside of a Herve Leger dress, I can not think of any exceptions to this rule.

style rule #3:  restraint. 

Yes, we watch the street, we watch the fashion shows, we have access to every great piece of designer fashion and fast fashion (except for the Target collabs – they sell out in minutes).  We love fashion and many of us are slaves to the industry.  That said, we do not buy into every trend story presented to us – stylish women know what is good.  And what will stay good for many seasons.

The stylish women of the world are not chasing trends or buying fast fashion – they are leading trends knowing what was presented last season, reflected again this season, and will show up again next year.  Stylish women pick one specific item to freshen a wardrobe and they pick that item carefully because it will be integrated into their wardrobe and worn until it falls apart.

style rule #4:  do something wrong. 

As the magazines have told you for years, you will rarely see a woman dressed head to toe in one brand.  Why?  Because it is boring…and expensive.  The chicest women get dressed perfectly and then adjust the outfit to make it imperfect.

madonna circa 1983 | image by kate smith  |  via national portrait gallery
madonna circa 1983 | image by kate smith | via national portrait gallery american cool exhibit

Let’s take the standard downtown New York all black outfit – jeans and tee or dress and tights, with boots, coat, and bag.  A stylish woman will put on this outfit and do one of three things:

– pile on very sculptured, structured jewelry ala an art director making the uniform a palette for a jewelry story

– ditch the coat and layer a sweater, a denim jacket, and a fur vest utilizing the textures to keep it visually interesting

– swap the black boots for brown or the black bag for a a bright leather tote

To be stylish, it is never right to look “perfect.”  You need do something wrong to be stylish.  The chicest women mess up perfection to make it interesting.  Perfection repels and interesting is a magnet.

style rule #5 (and the most important rule of all): Confidence.

I have a friend who was travelling to Vegas for the first time and she asked what to pack.  I said,

“Anything you own.  You will look great because you are a stylish New Yorker.”

“What does that mean?”

“You know, you have seen it all, know what’s good, carry yourself like a confident woman.  Even if everyone shows up in cocktail attire and you are in jeans, a t-shirt, a fantastic blazer, and great shoes, you will be fine.  It is all about how you carry yourself.”

lauren bacall  |  national portrait gallery
lauren bacall | image via national portrait gallery american cool exhibit

Stylish women remain unruffled, projecting a “been there/done that/will do it again” attitude.  Before a party we may ask friends what they are wearing.  But even when we decide to wear cocktail attire on the phone, we may change our minds at the last-minute and decide to wear black jeans and nice earrings.  Stylish women don’t think about looking different because we know we look great and are just ready to have a good time!

Yes, a nice dress, a great purse, or a new pair of shoes is always fun, but what is more fun?  Being present in the moment and spending time with our friends.  Not even the most fabulous dress can save a night when you are not having fun.

Fashion, like a great painting or wonderful song, is always a bonus – but not the point of the experience.  Stylish women know that and embrace it with confidence.


Here’s a quick recap of the five rules of style:

Skincare over makeup.

Proportion matters. 

Use restraint.

Do something wrong.

Confidence trumps all.

Did I leave anything out? Know a sixth rule I must add?  Drop me a note or comment below or track me down on twitter @jamesdrygoods – I would love to hear from you!