It’s about your hair. Or lack thereof. More specifically, it’s about your accessories, of which, your hair might be most important. Whatever your gender. If your hair, shoes, jewelry, and makeup (if you wear it) are right for you and the occasion, you could be wearing a potato sack and people will be dying to know where you got that cunning, anti-art, Dada-esque burlap tunic. Likewise, the most beautiful handmade couture / tailored garment will never save poor shoes.

Accessories communicate your personal philosophy and approach to life.
They’re not as constrained as clothing by the geometry and physics of body mechanics, allowing for more freedom of expression. Jeans and a tee with shiny black stilettos and a brass knuckle three-finger ring send a completely different message compared to jeans and a tee worn with Birkenstocks and a freshwater pearl necklace.

OK, style is actually about health and confidence, but you already knew that. The following is about surface style, so if you’re satisfied with ‘health and confidence’ as an answer, I will lovingly bid you adieu.

Your hair / head defines your silhouette:
James Dean’s pompadour; Janelle Monae’s pompadour; Anna Wintour’s samurai sword bob; Solange Knowles’ natural ‘do (left); Stephen Colbert’s suave waves, complete with raised eyebrow (right); Jason Statham’s scalp / beard combo buzz; Prince’s shag-n-sideburns; Ellen DeGeneres’ blonde pixie; Penelope Cruz’s brunette cascade…. If you have the resources of Miley Cyrus or Rihanna, by all means, change your hair every month. That can be fun.
But it’s not a necessary component of what constitutes personal style (not to mention it can be murder on your hair, but you already knew that, too). Nor are you required to shell out for $400 haircuts. It does require looking for help that you trust and that does a good job, which is just as likely to be found at the corner barber or the haircare chain as on the high street.

If your bald, or getting there, go all the way.
Poor Donald Trump. The slightest gust obliterates his self esteem.
Bald is dead sexy and confident:
Bruce Willis, Michael Jordan, Vin Diesel, Dwayne Johnson, Channing Tatum – when he feels like it, and, of course, the original bald man of action, Yul Brynner (left). Women who’ve shaved their heads and felt the freedom include Sigourney Weaver, Lupita Nyong’o, Demi Moore, Natalie Portman, Grace Jones, Charlize Theron, and Cate Blanchett (right).
I wish I had the courage.
Alternatively, I once met a woman who’d suffered severe hair loss from chemotherapy and decided to weave small narrow feathers into the tiny fibers that remained. They shimmered and floated as she talked and moved, to an ethereal and beautiful effect.

As for shoes, jewelry and bags, consider them as investments more important than your clothing. Again, whatever your gender. Shoes come first. If you expect them to be comfortable and last for years, they must be leather. No plastic. Roman legionnaires could never have marched thousands of miles in polyvinyl chloride. My admiration goes out to the vegans amongst you, but your feet work too hard to be supported by irritating, rigid synthetics that do not stand up to decades of wear. They must also be lined in leather or they will be still be uncomfortable and make your feet sweat, as synthetics don’t breathe. A waterproof breathable membrane like Gortex, which comes the closest, might be the only exception. Bags and jewelry are maybe equal in importance, depending on your preference and lifestyle. If you live out of a suitcase, then bags are the priority. Spending hundreds in these areas is appropriate. You’ll be using these items for many years, giving you long returns on your investments, at decreasing costs per use. Spending thousands is not necessary, unless you’re commissioning original work. They do not need to be designer brands. In this era of global access, DIY, and maker culture, logos are losing their meaning. Certain designer handbags are still considered holy grails, but brandishing them communicates very little about you or your personality, except that you wear what other people say you’re supposed to be wearing. Gone are the days when fashion was dictated. Besides, they no longer automatically represent the best quality or business practices. If you’re ready to make a high-level purchase, a better cultivation of your personal style would be to collaborate with an artist by commissioning something original that isn’t mass-produced. Whatever your budget, you don’t need a lot. You’ll find the 80/20 rule applies to your closet. But those workhorses that make up the 20% must be of the highest quality you can afford, and of a sort that transcend trends, which will enable you to wear them almost constantly throughout the seasons, year after year. They will likely be some take on the classics, with an element that enhances an aspect of your personality and suits your coloring and body type. They should mold to you and your lifestyle so well you could sleep in them. If you misplaced them at work, your colleagues would know exactly to whom they belong.

WOMEN – I will admit, like most women, I have a shoe fetish, which forced me to collect many pairs over the years. But, like I said, I wear 20% of them 80% of the time. If you’re as confident as Katherine Hepburn was, you could work every situation between four or five pairs. It is certainly possible to be very well turned out with eight or nine pairs, more or less, depending on your job and the climate where you live – black heels, nude heels, flats/loafers, boots, sneakers, evening/formal, one or two pairs of pretty sandals (I think flat-ish is most versatile…super-high heels in super-hot weather always strikes me as trying-too-hard), and a glamour pair. I have a leopard print peep-toe stiletto calf hair pair with a brown suede heel and ankle strap that go with just about anything and make me feel like Marilyn Monroe. Make me walk like her, too. If you do manual labor, see for men below, and swap out nude heels for brown shoes, add flats and sandals, and build from there. Find a signature piece of jewelry, or two. It certainly doesn’t need to be diamonds, or pearls, or boast any gems at all. It could be wood, enamel, or glass. It should make you gasp when you first see it, like a love you’ve never met before but feels like you’ve known forever.
It must complement your frame and coloring, and your lifestyle. A ring with a one inch profile has no chance of becoming everyday wear for a sculptor. If you can’t find what you’re looking for, consider commissioning a piece from a local artist. Or consider that anyway. Or, perhaps you’re lucky enough to have inherited a beautiful family heirloom. Wear it with pride and gratitude, and take good care of it. If you wear glasses, invest in good frames that complement your face shape. Ask for help if your confused, and take the time to try on lots of pairs.

MEN – It’s relatively easy for you, you lucky devils. You really only need one excellent watch, one good, not-over-stuffed wallet, two or three good belts, and five or six pairs of shoes, depending on your job and the climate where you live – two black (or one black, one dark cherry/cordovan – so dashing!), two brown, kicks, and work boots. If you do manual labor, you might have three pairs of boots, sneakers, brown and black dress. If you buy only one good pair, make them black cap toe oxfords. They’ll get you in anywhere, formal to casual.

If you have two brown pairs, one might be suede, which most still consider strictly casual, not to be worn with business suits. It depends on you, your job, and the suit. Learn the traditional guidelines, then deviate strategically and authentically. Get good frames if you wear glasses. And a luxurious wool scarf for winter, like cashmere or vicuña. Find one that amps up the color of your eyes. Keep it somewhat dark and somewhat muted and you won’t look like a tragic hipster, I promise. You’ll love how it feels so much you’ll look forward to cold weather. If you’re considering a facial hair style, keep in mind it’s less a pass on shaving and more an added maintenance routine. Finally, go very light on the jewelry. Or skip it all together, except a wedding ring. Women aren’t impressed by flash. They’re impressed by understatement. A powerful man who doesn’t flaunt his power is intoxicating. Anyway, you want to let her be the jewel. If you have extra cash, consider spending some of it on manicures. Again, it won’t make you tragic. Between King Midas and a blacksmith that cares for his own hands, I’d have the blacksmith.

Finally, you must take care of your investments. It is not a waste of time, it is another aspect of self-care and self-respect. Find a good cobbler and treat him or her like family. Good shoes can last 20 years, or more, if repaired along the way, and it’s cheaper than wearing them out and replacing them. Do as much as you can at home: regular cleaning, polishing, and covered storage, or on shoe trees. The cobbler puts taps on the toes and heels of my flatter shoes (something I saw my father request for all of his shoes), and pops rubber heel caps onto my stilettos. Or, if I wear the shoes a lot, I will have the ball of the foot of my leather soles covered in a very thin sheet of rubber, as leather soles can develop holes. I would even cover the red soles of a pair of Christian Louboutin’s, with red rubber, because the red lacquer wears off, and Louboutin doesn’t offer sole replacement. Soles on dress and lug-soled shoes usually can be replaced, depending on the quality of the shoe and the skill of the cobbler. Handmade shoes can be repaired from top to bottom, and I can’t help mentioning 100-year-old, US-based Red Wing boot company, who develops relationships with their customers by offering repair packages and services on their products for as long as you own them. Bags require similar cleaning and polishing to shoes. You can use neutral shoe polish on any color of leather bag (or shoe), and take care with the hardware. If you really want to go the extra mile, apply a small amount of neatsfoot oil or lederbalsam to your luggage and shoes a couple times a year, preferably with a sheepskin swatch. They can darken the leather a bit, so test a tiny amount and be prepared. Keep suede brushed and sprayed with protectant. Clean scuffs from patent leather gently with a q-tip and alcohol, or try the product Vernis Rife from Saphir. Avoid using acetone (nail polish remover). Patent leather items should always be stored protected in a bag, even one shoe away from the other, as the lacquer can transfer color from items next to it. Clean your fine jewelry regularly with appropriate metal polish. Don’t use toothpaste, which is convenient, but harsh. Keep pearls in a velvet bag. Store jewelry, both precious and paste, away from perfumes and cologne.

Developing a signature style doesn’t happen overnight. It can take years, but experimenting is where the fun is. Get off the beaten path, and learn to trust your heart and your gut, because it’s your life. Make it a priority to travel, even if it’s just across the state. Stop coveting what everyone else covets and open your eyes to the world around you. Don’t worry. You won’t get it wrong. Self expression isn’t astro-physics. It’s fun and games. Get stuck in. Take the plunge. Try something new. Fuck the fashion police. You might be so inspired as to learn to craft some of your own pieces, then wear them. You’d become a true original. Tune into yourself and become your own best stylist.