The Importance of Being Hip: After Hours Casual Attire.
I think it is important for a man who loves clothes to be Hip because all Hip means is for him to be both contemporary and fit in with the moment. That does not mean he has to be fleetingly fashionable. Someone whose clothes look traditional but also up-to-date would be ideal. Well, ideal is a bit dogmatic when employed for this objective. Further, I am not sure whether such a thing exists. Sometimes you have to decide what looks good on you by what looks good on others, which may or not work on one’s self. For instance, that bright yellow zoot-suit which looked terrific on Cab Calloway, may never look good on anyone else.
Extreme exceptions aside, we do indeed learn to dress by observing others. But because we have fewer well dressed people to serve as examples either at work or play, there exists a constantly shrinking set of examples for us to develop our own style around. To make matters worse and unlike with day wear, there seems an absence of agreement amongst men about what a man should and should not wear for “stepping out.” However there are a few guiding principles that can help make it less painful.
First, realize that the many “worlds” some of us can belong to may make our lives look a bit like a Venn diagram and each can call for completely different attire. The smaller your circle or association with different social worlds, the tighter your choices and the more signals you send off if you make the right or wrong choice in clothes. The only choice that cuts across all lines these days is appearing somewhere in your work clothes which might send the common signal that you have just pulled yourself away from your desk and are stopping by for a tense, inattentive moment rather than a fun filled evening to meet new people.
Or even worse, you brought your work attitude with you and are treating this gathering like a business meeting. That is perfectly acceptable if your company is hosting a fund raiser (Make sure you wear your corporate logo lapel pin!) or if you and your significant other are meeting for dinner.
Generally speaking, it is more polite and people will perceive this to be the case if you change specifically for an after hours event. I know some are rolling their eyes thinking, but I work until 9pm every evening how am I going to realistically change? My answer is take some cologne and a more informal shirt (and tie) or a sweater to the office on a day of an event. If you don’t wear informal shirts, sweaters and cologne, you may be beyond my help.
When I approach what to wear for going out, I generally approach it using items similar to what I wear to work but translated and deployed differently. As already touched on, it can depend heavily on the type of crowd that will be in attendance and whether you want to blend in, stick out or arouse comment. Age may play a part; your actual age, your apparent age, the age of the group, the age you feel.
Your target audience may likewise influence your choice. Ask yourself; is the place (and the crowd) old world or new world? Further, do I want to fit in with my peers or do I want to stand apart? Remember that many of the basic sartorial questions now answered for men’s daywear were once the subject of conjecture and similar questions were once asked of the wearers about the appropriateness of a particular item of clothes.
In any case, I have found that either wearing a very straight and narrow casual outfit or (using my same approach as with black tie dressing) one attention getting item is best, as in navy single breasted suit, brown suede shoes, orange plaid on blue button-down shirt. This assumes you aren’t attending a Burning Man after party of course.
If you are invited to a piano recital or to Smith and Wollensky for some steak and scotch, then you will probably be expected to wear a more traditional outfit. Work clothes are actually appropriate here. Although for the steakhouse a dark double breasted suit with a nice necktie is one of the few times a man can wear a good quality white tone-on-tone shirt without looking like he doesn’t know better.
Do you want to have a separate wardrobe or just re-invent work clothes for an evening out? It seems most men in the USA are unwilling to have separate wardrobes for casual. In the UK, it is still common to have suits which are casual (They would be work suits by American standards) worn with a more casual shirt, an open throated shirt (although cravats are still relatively common in England and maybe should be revived here) or (gasp!) more and more, an open throated button down shirt. It seems the button down’s functional design is contaminating our cousins across the herring pond.
Italy is very much a coat and tie country and even in small towns the men wear day dress all the time. But then their aspiration is the England of our imaginations, even if they realize it in lighter weights and more interesting colors while they strip every clothing article of its social label.
Although the English would feel a little uncomfortable at the idea of a tweed patterned jacket for city wear, for Americans it may not hurt to buy a sports coat or two specifically for city functions. This is the time when a bit of silk in the jacket says” evening out”. Other than that, and the use of darker colors sometimes, the jackets would usually follow the standard Anglo-American aesthetic in terms of color and pattern.
Being appropriately Hip also relies on certain assumptions, that you are not going to a counter-culture spot, that it isn’t for business, but rather to socialize and that you reside in a fairly urbane environment. My suggestions for what to wear stylishly for an evening in a suburban mall would differ greatly than for a Hip, downtown Chicago restaurant.
Assuming you’re converting work clothes, and assuming you’re in either a temperate or maritime climate:
Generally, the same colors for work also do for the nightlife but mostly in solids. Sometimes a striped suit works if you wear say a Duchamp style shirt and tie with it but, in general, solids (and many windowpanes) have escaped the business association.
An open necked shirt works. I wouldn’t do white without a tie, unless the white fabric was by its texture unsuitable for daywear. For shirt choices, black, navy (sometimes with white stripes), ecru and shades of grey (sometimes with a pattern.) are on board the Hip jet plane. I don’t think the English will ever take to black shirts but we can use them for limited purposes. The tonal similarity and the keeping to dark colors always seem to both modernize and make casual the outfit. Also (with some exceptions) would not advise letting a white t-shirt peek out of that open necked shirt (except in certain specific situations), better to have a nicely finished black t-shirt in mercerized cotton underneath this ensemble.
And about dark shirts and when you should wear them, consider again the crowd. If you are with your crew in NYC at Tabla looking to meet the models, then a black linen shirt under your charcoal suit with closely set double track beaded pinstripes is in order with black calf chelsea boots. If you are at Le Cirque 2000, then a rich Wedgwood blue sea island shirt with French cuffs under a medium to dark double breasted bird’s eye patterned suit with a beautiful woven tie and a pair of dark brown suede brogues is much more refined Gotham.
The English are an inspiring study for casual shirts. What they consider one of their little sartorial liberations at the office, the Americans still have not completely adopted. Their boldly patterned and colored shirts in the Turnbull & Asser, TM Lewin tradition are salient because of social pressures applied to other areas of the water balloon which constitutes their wardrobe.
Although it is true that American attitudes towards what constitutes acceptable business shirt colors and patterns have relaxed in the last decade, they still have not caught up with the English. But for casual, we now combine the sartorial expressions of English bold shirt fabric with the functionality of the button down shirt. Thus in summer, the orange butcher striped button down shirt is Hip under a blazer or with a pair of odd pants.
You can wear a necktie too. Just try not to select something that looks like a business tie. Perhaps a rich woven necktie, maybe one that’s a bit too rich looking to wear to the office. Again, the English come to the rescue with the Turnbull and Asser or Duchamp tie. However, there are many other examples of ties which give a more casual air to one’s outfit. If it’s a night out with her to someplace like Balthazar in NYC a navy jacket, medium grey pants, dark brown suede shoes and a shirt with mixed blue and mauve (or lilac) stripes or checks and a magenta, lavender or purple grenadine necktie from www.samhober.com is what I call Hip.
Knits work well too, at least for the torso, generally in dark solid colors. Sometimes, depending on such diverse elements as your coloring, the item’s coloring, the season/weather, a more brightly colored knit is acceptable. There are so many factors that play a role here it is a little difficult to lay down more than guidelines.
There are times when a flannel or cashmere navy jacket and grey pants should be graced with a tangerine or fuchsia mock turtle neck cashmere sweater. Alternatively a medium to dark grey flannel suit could support the occasional oatmeal colored cashmere sweater while a light grey one would pair well with a sweater in burgundy or eggplant. If it’s the dead of summer, I don’t mind an aqua blue, fuchsia or a white polo shirt under a jacket. Just make sure it’s good quality with a fuller collar that stays under the jacket and that it is in good condition. The Lacoste shirt in white under a blue summer weight jacket is a Hip perennial.
As you may have surmised, brown suede shoes are good for casual outfits because they have the same softness and lack of business pushiness as does flannel. I sometimes like them with lug soles if I am in a location where the floor may be slippery and I am indulging in a few libations myself. Also, the realities of winter in New York City sometimes demand better grip for our slippery pavements. Paired with brown suede or calf leather belts, these shoes lend themselves to a more relaxed casual and yet stylish deportment.
Part of the problem (and the fun) with casual dressing, is that it is harder to get it “right” and it has a lot more specifics to the individual, time and place. It takes a bit more thinking and less regimentation. I doubt if there are any rules per se, but there are definitely variations that cause less inflection in the mind’s eye of the observer (including yourself, of course) you may be dressing to please and impress. Depending on the weather and the place a nicely hand finished t-shirt in cashmere can look stylish under your jacket.
A lot of it depends on what image you are trying to present and to whom. Add to that, what constraints do you feel prohibit you from wearing certain looks. For example, it took me a while to get passed not wearing a tie with a suit, now I happen to like the look if it is done well. Further, what attitudes do you bring to the dressing table? If you consider this as an X, Y graph where X is what others think and Y is what you think, it plays a role in what you are going to feel comfortable in. The one thing you shouldn’t do is proceed without reflection because you may not be presenting yourself in the light you think you are.
There are several different types of Hip:
Hip does not necessarily fit into neatly separated zip locks. There are gradations. Old-Boy-Hip is one of these.
Old-Boy-Hip is tricky because it encompasses two concepts. The first is simply the traditional Anglo-American style with some creative elements such as the patch madras or tweed jacket, the fancy dinner jacket waistcoat or the brightly striped blazer. These are all part of that kicky but decidedly “Fogey” world of clothes. If you’ve ever seen the candy canes on the bright green wide wale cords around Christmas time, you’ll know what I mean.
The second concept is that Old-Boy-Hip takes standard up-to-date fabrics that simply say they are right for business but also of the moment. Italian fabrics are considered and fabrics generally are lighter in weight, finer, and softer… oh and a slight sheen is acceptable (At least for summer). Basically this is the “in touch” professional’s look which acknowledges the past without wanting to slavishly replicate it.
For instance, I have a cavalry twill fabric (from the cloth Merchant, Scabal) I am looking at which is only vestigially like the original cavalry twill. It is nearly half the weight (9oz) and it is relaxed and smooth and soft (buttery) and about as far away from Old-Boy cavalry twill as one can imagine. It is still identifiable as traditional and yet is also Hip because it is an up-to-date interpretation of the look. It is just right for the silk and wool windowpane jacket I have placed it next to, a jacket which is decidedly Hip. With a worsted cashmere navy blazer, a pair of medium brown or green pants in this fabric (well just about any of the fabric book’s medium to light colored choices) is sublime.
Actual Hip denotes the casualness of dressing for women, for the evening, for modernity and to a certain extent, the sloughing off of tradition and the class associations that bind. A Hip jacket or suit is often more at home with a sweater than a shirt and tie, sometimes even more acceptable with a hand finished t-shirt in a mercerized finish. But the look of Hip is an interclass look which still has elements of tastefulness to it.
Everyone appreciates the Hip look because it is expensively done, it is very modern, it is appealing to people who you might want to congregate with but who are intimidated by the office and the idea that you might be insinuating your superior pedigree on anything other than merit. Hip is a very democratic and inclusive look which nevertheless relies on a certain amount of taste either on the part of the wearer or the person who selected the clothes.
However, Hip can also be tweaked from situation to situation and social set to social set. Consider the mercerized cotton, hand finished t-shirt. In black, it is right for the night. In navy or royal blue, it looks more genteel under a lightweight, open weave navy jacket with white pants at the marina, in white or pale blue its ready for a stroll under a coral linen jacket along a Caribbean beach and in chocolate brown with jeans it’s right for listening to an alternative band’s gig.
Just as there are different types of Hip for different circles of people or events, there are within each specific circle many degrees of being Hip. True Hip clothes you wouldn’t wear to the standard conservative industry office. However, there are clothes that can be used as Hip which are perfectly fit for the office if you swap out the wrong accessories and swap in the right ones.
But the true Hip look (which can be timeless mind you and is not the slave of fashion) deserves its own wardrobe because it has its own fabrics and its own cut and details. I am not suggesting that the absence of these specific items makes you look less Hip, so much as I am saying the presence of them makes you look more so. Again, I realize that most men will have no interest in a completely separate wardrobe for this look but we are dreaming about the ideal state of affairs.
Think about the messages your clothes send off. Hip says, I may be a dilettante or run a corporation but tonight we are all equal and ready to socialize or party on a level playing field. Even differences between Hip and Old Boy jacket silhouettes can say things about you. Old-Boy has a more military look to it and even if the shoulder is natural it isn’t necessarily sloped. Optimally, the Hip shoulder line is slanted downwards, at ease, less military, less aggressive, and more inviting especially to women. Fabrics are likewise invitingly soft and touchable especially to the hands of that special someone you want to meet and get close to. Business clothing is more of a warning and demand for respect and personal space; Hip dressing is all about being surrounded by an entourage, even if it’s simply an impromptu entourage du soir.
There are those items which transcend the separation between day and evening purposes. For trousers, the reverse pleat is both professional and casual (and Hip) that is to say, the Neapolitans like it, the Milanese, New Yorkers and the English too. Reverse pleats are fit both for today’s business suit and for the evening style of true Hip. I like tunnel loops on my pants which are Hip for evening and also good for the office as an individual custom touch which often serves as a conversation piece. I happen to like them because I am a baseball fan (I am a football fan too but I haven’t figured out how to work that into the wardrobe), and this can segueway into very interesting conversations about sports, or if nothing else makes for a good story.
Contrast the above approach with full blown Hip where its all about night and the city. There the camouflage is influenced by asphalt and marble and stainless steel encompassed by mood lighting. Full blown Hip is also exhibited by the sportscasters on ESPN. I may disagree with many of the jacket details and styles but the fabrics, the color combinations between jacket, shirt and tie are very Hip and up-to-date, mostly right for after hours. I don’t think that’s an accident.
One caution when wearing the “all black” look or using the black pants and/or torso covering under a jacket is employed. When it comes to wearing black or black torso coverings, which is very common for Hip style as it is essentially a modern-city-party look, I want to say that there is one unfortunate effect Hip dressing can have that old boy dressing doesn’t ever seem to. It accentuates what you look like. If you look like a wimp it makes you look wimpier. If you look like a bouncer it can make you look like a hit man, if you look effete it can make you look more precious. That is why when wearing “all black” or a predominant amount of black, its components have to be carefully made and finished and have to be and be maintained in a state of true black-black color.
Hip dressing can be tricky with even the smallest detail done wrong ruining the whole look. Now, if you do the Hip look improperly you can move yourself into what a lot of people fear which is “slick” the so called Garmento look which translates into:”Cheap Hood”. However, that doesn’t ever have to be the case. All you need do is follow the guidelines and avoid the pitfalls. Let me be your lantern bearing sartorial Virgil.
We have covered some elements of relatively timeless Hip and, I should add, a traditionally tailored Hip to boot. There is also extreme Hip or Hipster and fashionably Hip (the Hip of Dolce et Gabbana and the designers) which I haven’t touched on. These looks are freely accessible in several popular “menswear” magazines.
The basics of this essay are complete but if you retain reservations about being Hip or what it means to be Hip, here is a friendly aside from Film Noir Buff:
Let me relate a story. Years ago, I realized I was showing up to parties and being routinely passed over for choice conversations. Now comments about my looks or personality aside, I realized that my outfits said that I was just coming from work and that I was dressed like what one girl described as a stuck up jackass. It was actually a little ruder than that but one never knows when Mom is reading one’s site.
I had a friend that worked in an elegant men’s clothing shop; and because he was also a man with a great deal of personal style, I asked him how you might dress for nightlife in New York City without being too trendy and garmento. I was in luck because he actually had a fun and active social life while also firmly rooted in the 1930s tradition. His answer was a style that’s actually called “Hip“… well maybe I invented that label.
Anyway, my friend helped me to see what was important with night time dressing. And yes, on the Upper East Side it’s a bit more traditional, but the prettiest are downtown these days. In any case, I learned the language. It’s all tailored by my tailor so the style is the same, but the choices are a bit more noir. In some ways the looks are timeless, they are just more relaxed. I have seen movies in the sixties where Steve McQueen is wearing a black suit with a black sweater.
Now, It took me a long time to wear a jacket without a tie without feeling like Tony f****n Montana, but I finally managed it. Understand that my entire upbringing went against it, my father being a very formal, buttoned up person (blazer at the beach). Let me tell you, I had anxiety over appearing in public in a jacket without a necktie on. I got over it though and so can you. Let this be your necktie shedding twelve step program.
Now, Ill tell you the difference not wearing a necktie with a jacket made on other people. When I wore a tie flirting with women was always awkward, I always felt stiff and uncomfortable. It was almost like at any moment they expected me to give them an order. In the tie less outfit, the same women would stop me, flirt with me, laugh, give me numbers, invite me to parties, look me in the eye, and touch me. I had gone from unapproachable corporate jackass to “it” boy. That is what I call tangible results.
So, before you assert that traditional dress was good enough for FDR, so it’s good enough for you (and the ladies), at least do some experimenting. Insisting that you are doing the right thing without really knowing for sure can run you into trouble with clothes inappropriate for the occasion.
There are several factors at work with all of this. On the one hand, you have men who with a mixture of fear and resentment refuse to understand that there might be a middle ground between dressing trendy, and showing up dressed like Thurston Howell III. No one suggested that anyone go out and start wearing Versace snakeskin pants. All the things Im speaking about, with the occasional odd piece for the torso, will follow traditional Anglo-American tailoring and shoemaking (ahem, except for an occasional lug sole).
Am I asking for a lot here? I don’t think so. A solid black suit in a light weight fabric, say a Zegna high performance and a black linen shirt, doesn’t make you a gigolo. It is a very smart look. It combines tradition, modernity, power and approachability, that’s why its been adopted by so many lifestyles. It has a bit of the urban commando about it, danger, training, honor, and mystery. Best part about it is there is no hair gel or chains that go with it. It actually has traditional roots in the 50s and 60s.
No one’s asking anyone to wear the blue shirt with the diagonal lighter blue stripes with the double fold cuffs pulled up over the jacket sleeves. The look I am talking about is still a quiet and refined look. And I’m afraid anyone who doesn’t think so is not enjoying clothes but rather hiding behind a social code. What do I mean? I mean that you’re the sartorial equivalent of the guy walking around in the frock coat, monocle and spats in the Fred Astaire movies. They too were smug in the fact that they knew better, but they were wearing the previous generation’s clothes and what fools they seemed; comic relief to an audience which wanted to enjoy the moment and not feel controlled by the past.
Again, it’s not about being trendy, just relaxed, approachable, fitting in with the night, with the party, with the black and white marble, the sheet glass and the stainless steel of so many urban haunts. It is hardly revolutionary, it is called being well dressed when to show up to those same locations in a blazer with brass buttons, an oxford shirt and boat shoes is about as proper as showing up dressed for a Comedia del Arte.