How to have your own Iconic, American, Vintage Style

With all the information regarding how to dress, finding trustworthy and mature advice on how to develop your own very personal, public persona (say that three times!) is becoming increasingly difficult.  Contrary to what you may believe the fashion industry is not primarily concerned with making you look good.  Most fashion businesses largely exists to extract your capital, which means a lot of change to make you feel like your look is obsolete and cause you to spend more kale.  With all this noise about how to dress, have you noticed how little listening is being done?  I’d like to diverge from the dictatorial approach to men’s style. Since you’re distinct in your own ways, why present yourself as average?  Let’s take a look at different approach to dynamic dressing. I call it Iconic American Vintage Style.

Understanding Iconic, American, Vintage Style

Ok, it’s a mouthful, and I have a very vivid sense of what that means, but I want to elaborate on it a bit to make sure you’re with me.  Iconic to me, means reducing things down to the essentials and executing them in a timeless way that seems almost larger than life. To be American is to be a part of the grand experiment. It means the eclectic energy and storied history of amazing times like the Prohibition era. It is belonging and being an outcast simultaneously. It is the frenzied search for identity in a place where almost anything is possible. Vintage makes me think of fine wine, of things made by craftsmen in this country and the pride that generates. It is a nostalgic longing for a simpler time where good music, friends and an honest day’s work was enough. It is faint scent of perfume from a letter written to you by a lover, carefully saved over the years and the slight ache in your heart as you reread it. It is Miles Davis, Kind of Blue and the melancholy sentiment that comes with acknowledging that the simpler times of the past are forever gone. Style is deeply personal statement of what you hold dear, expressed by the way you present yourself to the world.  It may evolve and change, but it is not frivolous or erratic.  Fashion is a societal statement defined by one group and then gradually adopted at varying degrees by the “me too” crowd. It is a fan who roots for whichever teaming is winning at the moment.   The key distinction between fashion and style is that fashion is defined from external sources (magazines, TV, retail stores).  Although style can be influenced by external things (history, old movies, big band music), it ultimately comes from the inside. My true goal is not to see you wearing Prohibition head to toe (as lovely as you’d look), but to chip away some of the propaganda so that you can decide what moves you, much like a sculptor removing stone so a beautiful form is revealed.

Ultimately, your style is a unique pact between you as a person and the clothes.  I can put you in a stunning suit and if it doesn’t suit you (uh, sorry), you’ll seem awkward and self-conscious which undermines both of us. Does this all seem like a lot to think about? With women gaining more of an equal economic footing in society (applaud here!), we boys have to step up and out from the crowd.  From dames, to the office, great style pays dividends. So let’s talk more about finding out what moves you.

Finding your muse: How to let your passion inform your style decisions.

Maybe you haven’t given this whole style thing much thought, it certainly is easier to just buy the look in the window, but maybe mannequin man is sterile for you. So, let’s talk about you for a minute.  Is there a time period that you find interesting? Maybe like me, you love the Roaring 20’s, Prohibition Era, and the galvanizing 40’s with the Great War. Do those old black and white films tug at your heartstrings? How about a drive-in movie with James Dean in cuffed jeans and a white tee? Or are the hot night clubs and cool jazz of the Harlem Renaissance true to your heart?

We want to make you the leading man in the story of your life, but you have to dress the part. How about Harvard prep school circa 1932, or a well-worn, denim utilitarian look with some really cool, vintage work boots based on the Great Depression? At this point we’re just searching for a time period to draw inspiration from. At some point I’ll try to make a questionnaire that will help you focus in on this.  Once you have a decade in mind, you can google “Images Men’s Fashions from the 19xx’s”.  This is going to start to give you some idea of how men dressed during that time and if you find yourself excited about what you see, that’s a good sign.  Spend some time here, look at a few periods.  Take a look at films from the period or modern films about that period.  Again, the goal here is to discover looks that resonate with you. I suggest printing the pictures or saving the links.  As you get further along, all of this will become more intuitive, but for now let’s make use of our visual aids. You can also blend from decades that are close unless the general fashion of the times changed rapidly. Men’s clothing in the 1950’s and 1960’s were quite different, so it’s unlikely both of them would speak to you, but the 20’s and 30’s, sure why not?  I tend to think of dressing like a Normal Rockwell painting, because I believe a good outfit tells a story.  I call this “narrative dressing”. Women can dress like a librarian one day and a madam the next and be sincere in both outfits. Being in touch with different aspects of themselves and embracing them is part of what makes them intriguingly delicious. We boys on the other hand, tend to refrain from such explorations, which makes for a much less compelling story.  Some of my characters are 1930’s newsboy (plus fours, argyle knee socks, bow tie), 1930’s Mob Boss (3 piece suit, clean and mean), 1930 Chicago street tough (a white tee or Henley, suspender pants, a fedora or newsboy), 1940’s Detective (Fedora, suspendered suit, tie). It may sound corny, but I even have names for some of these characters. The way I feel in plus fours is certainly different from the way I feel in the “Chicago” look. Understanding that and letting each outfit have its own breath is the icing on the cake that makes everything come together in a way that is bigger than life (Iconic). When I step onto the subway, fedora cocked low and tilted, eyes narrow and jaw taut, I bring that gritty, sexy, darkness with me and visually invite other riders into that story. Or maybe today I’m serving 1930’s Newsboy, young and charismatic. Once you have your decades and found some key images that move you, we’re ready for the next stage.

The Dress Rehearsal

At this point, it’s time to test drive some looks based on your target images.  We need to see you in some outfits based on your images.  The best place to try on some things in a relatively low pressure environment, with a lot of variety, is your local vintage store. This place will eventually become a staple resource for you, so make sure to be nice to the staff.  Later, they’ll call you first when good stuff comes in that fits your style and often you’ll see it before it even hits the sales floor.  Take your images along and go at a time when it’s not busy. Oh, almost forgot, wear the right shoes! It’s hard to feel like a 1930’s gangster in Air Jordans. I’d tell them something like “I really love these old detective movies from the 40’s and I think these clothes look great (show them images).  Do you have anything like this I can try on?” If your detective wears a shirt and tie, have these items on when you go shopping. That way, if you put on a vintage suit, the other parts are at least reasonable. If you can, get the right hat FIRST!  Up to 1950 men wore hats daily, so having the right hat will make a huge difference in your look.  When I find great vintage hats, I pay top dollar for them.  This is still about 30% to 40% less that buying a new one.

Okay, once you’re all dressed up, time to hit the mirror. Ask the salesperson to let you marinate in the outfit without comments for a minute. Here’s the big question:  How do you feel in this outfit overall?  We’re trying to get a sense of the whole look at this point and how you feel in it. Move around in it a little bit, take your hat off, and put it on again. If you decide you like the look, you can start to analyze the pieces. Pants a little short, check the inside to see if they can be let down. Hat feels tight, ask the staff for are bigger sizes around. Fine tune the outfit a bit. Try on a few other outfits.  If you find something you love you can either buy it, or see if they’ll hold it for you for 24 hours.  If you’ve never bought a real fedora, you might not realize a good new one can easily cost $200 or more, so the $50 vintage one may seems pricey to you. The hold period gives you time to comparison shop and make sure you’re getting a decent deal. If you can visit multiple vintage stores on the same day, that’s ideal. Ask the staff if they know of any places to get vintage reproductions, or items similar to your images.  Most men’s clothes pre 1940 are hard to find since they were well used and often wore out.

Next, take a trip to your local better department store.  We’re going to run the same exercise here, so same rules apply. Show the salesperson the images and see where they direct you.  Some things, like wider pants, which are currently out of fashion, you may not be able to find.  Always look at quality goods, meaning don’t get stuck on price yet.  You don’t want to look like you’re wearing a cheap Halloween costume, so we have to hold the standard.  Don’t worry, I’m going to help you find some great stuff at a budget and give you a new way to examine value in regards to clothing. Some items, you will have to spend some coins on, but these will be items that will help define your style for years to come, so they’re still a great value.  Oh, forgive me.  It’s very unromantic of me to talk about value.  Doesn’t it seem like Designers rarely use terms like that? Somehow they assume you’ll dig up $250 to buy their ultra dark, “skinny jeans” which you have to dry clean inside out and still the blue dye rubs off on your white shirts. Next year they’ll tell you “fat is the new skinny” and acid-wash is all the rage and it’s back to the cash register again.  All this change for its own sake and unconsidered consumption is a bit vulgar.  When I traveled to Italy, clothes (of Italian origin) were well-made, but quite expensive, so people tended to wear things over and over again. So you got used to seeing Luca and his blue twill blazer or Filomena’s tweed cardigan.  These items became signature pieces that you associated with them.  So the mantra is “Less clothes, better clothes and more of a visual impact”.  American tend to have 800 pieces of poorly made clothing and none of it is worth remembering, like having lunch daily at clown burger. Sorry for the monologue, but very important concepts to note. Hopefully you’re discovering some clothes that are not only beautiful, but really feel like you.  Let’s take a quick sidebar and discuss how you should determine the true cost of what you buy. This will help you understand where you can shop and you’ll probably de delighted to find out you can spend more on some things than you thought and actually save money in the long run. Don’t skip this part since most of us are trying to dress well, but do have a budget to consider.

Clothing Calculus 101:  Understanding the Cost/Value Relationship:

So now you’re starting to see some clothes you love and that really fit with your emerging style, so that’s great. Unfortunately, like most of us, you’re on a limited budget and some of these vintage items or reproductions seem really pricey.  You want to know how to tell when something is a good deal, and when to walk away. Here’s the big concept.  Value=cost/number of wearings or cost per wear.

For example, my $300 Allen-Edmond cap toe shoes, which I’ve probably worn 75 times a year for the past 5 years, currently value out at (75 x 5=325 wearings so far). $300/325 wearings=.92 cents per wear.  Let’s not forget that these shoes still look awesome and that AE has a resoling program, so it’s likely I’ll get another 5 years out of them with a little maintenance. So maybe the final cost per wear will be something like .60 cents per wear. So I get to step out in beautiful and comfortable shoes regularly for less money than it costs to buy a newspaper.

Let’s contrast this with the new Air Jordans. At $189 a pop, they’re not inexpensive. You can’t resole them,   so there is definitely a finite number of wearings  in them.  I’m going to say they’re less versatile since you can’t really wear them with a suit and jeans. I guess technically you could do that, it’s just that you wouldn’t get in most of the places I like to go.  In a year, when the newer style Jordans are released the appeal of these Jordans will plummet, forced into retirement by the same cats who sold you the first ones.   So I’m going to be generous and say you can wear these for 2 years at the same 75 wearings per year, so that’s 150 wearings before they die are or obsolete. So that’s $189/150= $1.26 per wearing, that’s about TWICE as much as my Edmonds. So the best dressed person is not necessarily the one who spends the most on their clothes. So that’s the very important Cost Per Wear concept.

Lesson 2: Old vs. New.  Due to developments in technology and the desire to make goods more accessible (less expensive) many new products are of lesser quality that their predecessors.  This is why I can still listen to my 1932 Wade Airline radio, but the television I bought about 6 years ago at Nobody Beats the Wiz is now landfill.  General rule: If you can find an old one that is in good condition and fits (or can be altered to fit) choose it over a new one.  Your job is to make sure you know what all the new goods cost at a comparable quality.  If you know a nice homburg hat goes for $89.00 for an S-XL version of lower quality to $229.00 for a nice quality domestic one, paying $159.00 for an exceptional vintage one on Ebay is a no-brainer. Make a list of all of the items you want, then watch your favorite brands for sales, search e-bay regularly (don’t forget ebay UK!), visit thrift shops and vintage shops.  Your father or grandfather may be elated that you’re interested in classic menswear and may have a stash they’re willing to share with you.  You can break the bank buying great clothes, or you can do the legwork.  I’m mostly explaining the latter, since it’s the insider’s way and you get the thrill of discovery. Most ladies will be more than willing to accompany you on these trips, so you can work a little and play a little.  Make sure to eat well before going and take your inspirational images.  The salespeople live in the store and want to make sales, so if you show them your list and images they can save you a lot of time and may pick up on something you would’ve missed.

Lesson 3: Use your friends wisely. If you happen to have friends that are makers, or work at a retail store, you may employ the “duke” system.  “Duking” is the practice of a favor for a favor, but particularly refers to the person who does the first favor without a negotiated exchange.  If I’m asking my friend at Brooks Brothers to buy a pair of shoes on employee discount for me, I’m going to offer them something nice in return.   Free alterations, merchandise, acupuncture from my wife, extra fabric I have laying around, any of these may make for a good barter and help me get something (like $500 shoes) that otherwise would be out of reach.

Lesson 4: Embrace the beauty of imperfection. Much like the Wabi-Sabi concept, clothes should be worn in an easy elegant way.  Imagine a leopard trying to distribute his spots evenly, or a zebra fidgeting with her stripes. Seems a bit silly doesn’t it? If you’re around the New York vintage scene, you’re probably familiar with Michael Haar. Beyond being a charming gentleman, he is also one of the world’s best dressed men, period.  Often seen in a three piece suit, he carries it off as effortlessly as the average man might carry off jeans and a white tee.  His early 1900’s look and striking mustache seem so natural, I can’t image him looking any different. As you blossom into your new style, be easy with it. There’s nothing wrong with a quick duck into the gents lab to refresh one’s look, but fidgeting, tucking, tugging, twisting, turning, tampering, and teasing in public is strictly verboten. Once the show starts, it must go on.

Lesson 5: Start with the foundation.  In the same way that the foundation of a building determines the height it can attain, the shoes you wear set the tone for your style.  Women definitely notice not only a man’s shoes, but their condition. A well-heeled gentleman in shined shoes says you are a man of means and maturity, and that you know how to attend to details.  That’s a pretty strong endorsement.  Great shoes, jeans, a nice shirt, bowtie and cap can make a great look. So buy the shoes first.

The next purchase you should make is one or two nice hats or caps.  I wear a hat every day and it frames your face, so get a nice one and remember a hat adds a lot of zip to your style and is relatively inexpensive in the cost per wear analysis. Oh, if you need to carry a bag for work that comes next. Get thee to Coach (avoid the heavily logo’d stuff) or your local leather store and get a handsome bag that has good pockets to keep you organized and can hold all the stuff you need.  Remember warm, vegetable-tanned leather looks richer than flat black leather goods and gets more handsome as it ages.  My daily carry bag cost about six hundred dollars at Coach, but they guarantee it for life. Imagine what the cost per use looks like on a bag I plan to carry indefinitely? When I’m standing on the NYC subway, I regularly see women notice my bag and then look up to see who the owner is. Oh, and expensive nylon is still nylon (man-made chemicals). Think leather or heavy cotton canvas.  If the basic material wasn’t around when your grandfather was your age, forget about it.

Now we are onto the flourishes. Bowties, pocket squares, glasses, watch, socks, card case, lighter, flasks, collar pins, bars, key FOBs, suspenders, etc.  All of these are small touches that will enhance the things you already have without breaking your bank.  Instead of going in for one suit, buy a variety or small accessories you can use to upgrade the clothes you already have.  This will make a bigger impact on your overall look than having one great item, which people will quickly tire of seeing you in.

You’re well on your way to lead the style parade and now are ready for a few custom pieces.  Go for a few wide leg trousers in earth tones and warm greys. The fabrics should be light to mid-weight wools that can be worn 9 month of the year (more wearability=more value). I never put my clients in flat, solid color fabrics that are visually uninteresting and appear inexpensive. Fabrics with slight textural effects and heather yarns are easy to match because they appear solid from a few yards away.  However, as one move’s closer and becomes more intimate with them the texture and subtle tones in the yard become evident. I like the idea that a fabric becomes more appealing as you get closer to it and generally find the same applies to people.

Shirts should come next in the line-up, but for the most point they don’t. Why? Well, thanks for asking. Shirts are considered furnishings for men and are usually a secondary consideration.  This is why they come wrapped in plastic and tucked away in a big retail honeycomb.  To me a lot of shirts don’t stand out, meaning I find neither the fabric, nor the design exceptional.  All of the collars we make have a purpose, a little something unique about them, that justifies their existence.  Remember, your shirt collar frames the bottom of your face and is important. I just think you should get some bang for your buck.  The other thing to consider here is your overall silhouette. If you’re wearing narrower flat-front pants and want a slim, clean look you need a more fitted shirt.  Our “Depression” fit tucks in neatly with minimal fullness and also stays neat under fitted vests and jackets.  If you like a little roomier shirt that blouses into your trousers, then our Custom Fit will suit you.  Customers who are local to NY are welcome to set up and appointment with me and I will create a Signature fit exclusively for you based on our review of your favorite shirt.  Working with makers, allows such innovation as a longer sleeve on one side and a bigger cuff for the arm you wear your watch on.  We also offer a contrast collar that references the removable collars of the Jazz Age and always looks crisp around your face.

Finally, we come to the workhorse of your wardrobe the jacket.  Here, I’m going to just give it to you straight. Buy our period perfect navy blazer!  The navy blazer in a light to mid-weight wool dresses up jeans, chinos, and dress pants.  I’ve even seen them worn with shorts.  Remember, the cost per wear thing we spoke about? Yes, gold star for you. This is a jacket you can easily wear twice a week most of the year. With its pleated patch pockets, back action pleats, back half belt and side vents, we’re clearly ahead of the competition. Drop a pocket square in the pocket and a flower in the lapel and your casual style is elevated to new heights and suitable for most county and city endeavors.

The suit comes after the trousers and blazer, because ultimately, it’s less versatile.  If you wear the jacket or trousers too often as a separate, don’t be surprised when the two items no longer match.

STAY TUNED FOR PART 2. I’ll go into the nuances of the suit and cover some other subtle but relevant aspects of fine dressing.  I hope this information has been valuable to you.   Please feel free to contact me at  if you have questions.