hip 2   (h p) also hep (h p)
adj. hip•per also hep•per, hip•pest also hep•pest Slang
1. Keenly aware of or knowledgeable about the latest trends or developments.
2. Very fashionable or stylish


That’s hip in a nutshell. Some flee from it, others feel like outsiders wanting in and still others take like it as a duck to water.

Hip is always more pleasing to women because it involves luxury, softness, up to date, approachable, successful, and expensive. You are James Bond without trying. You’re that modern man she’s been reading about and who wears those things that are always appropriate, you are never her father’s wardrobe only that man of mystery, even when she feels safe with you. You are Hip.


The concept of being hip in terms of style and clothes is an elusive one. Not easily explained, not quickly learned; at least not verbally. The idea of being hip triggers so many different reactions that sometimes the term itself may be counterproductive. Those who don’t feel they’re hip find that the very subject has them at a disadvantage, and those who already think they are hip scoff at the idea that they need to learn anything new. But hip isn’t just a dressing style, it’s an accent to the language of clothes that can make anything one wears in any situation that much more current. Being current is important because you are taken the most seriously today and maybe for the future. It is exactly the opposite reason people giggle at the passé.  There are many different degrees of being hip and though it may just be a subtle message sent to the observer, it can still be powerfully suggestive.

This is why I split hip into different areas:

Old Boy Hip- has the look of the old money past but everything is made the best it can be and recently. It can apply to those situations at work or after hours but follows the most rules. Even the oldest firms change with the times. A Huntsman suit made today is a lot more hip than one made a decade ago even if theoretically the suits were cut using the same pattern. Sewing techniques change, cloths change, details change, lapels change. It’s foolish to pretend otherwise. This look is proof that you can be Hip merely by having relatively newly made suit/shirt/tie/shoes and hopefully, socks.

Hip- Has a disassociation with the old world. It still relies on some basic elements but it contains a certain rebel or counterculture streak to it. It also acts as a level playing field to disguise class or other irrelevant factors to express a “cool” forward looking “togetherness” of ideas. I only separate it from afterhours hip because I assume these are items that you would also wear to the more forward thinking offices, otherwise Hip is a subset of After Hours Hip.

After hours Hip-  Can span the gamut depending on the crowd, the place and the nature of the wearer. The important thing is do something well from the choices at hand not to scoff at the look in general. Use desert island example, picking the right knit shirt to wear. In some ways this is the broadest because as mentioned time, place, manner, weather, wearer play a huge role. If it’s a jeans wearing situation, that’s so different from a brand new nouvelle restaurant situation.

Cutting edge Hip- Has a hand with the designers and is sometimes way to fashionable for serious office workers but nevertheless for casual and some industries it can be de rigeur.

Discuss the fallacy of wearing certain things because they have age associations because though part of being hip is referencing what everyone else is wearing like Old-Boy-Hip references the traditional past but you still want to look individual and different as well as choose from those things that flatter you vs. those things which you feel you must wear. I had a girlfriend who looked better in the brown dress but she just wanted black because everyone else had one ex.


Paul Smith: Then there’s the swinging London corollary which is a bit too colorful to be classified as standard hip and a bit too classically tailored to be considered cutting edge hip. It’s a very English phenomenon and a lot of it works in relatively conservative offices in London because it’s the sort of hidden message goodies the English love to wear.



Sometimes Old world things worn tongue and cheek look more hip than forcing yourself to wear  things which you think are appropriate for your age. This can be as comic as wearing things not appropriate for your age, which seems to be the bigger concern. Wearing things that you and your personality can carry off is a lot more to the point of knowing thyself which is sartorial chi and about as hip as you can be.

The one that most men struggle with is After Hours Hip. After all, for Cutting Edge hip all you need to do is flee into the all encompassing arms of a designer.
Think of Hip as an amalgamation or a fusion of several different worlds all crisscrossing at night time. Without suggesting comparisons between each group or genre, these are the worlds that have contributed heavily to the Look of hip. Organized crime and fashionable secret agents (often international, often from the movies), alternative lifestyles, Hollywood and sports and music figures, African Americans, Fashion Designers, The smart set, International intelligentsia and not so intelligentsia. All of these elements are in the pot pourri of hip, each one of them has their extremes, the more you want to look like one, the less you look like another; like a many ringed venn diagram. If you want more of an element of danger, perhaps add more organized crime, if you want more playboy, then go in the direction of the smart set or Hollywood, if you want to look more fun and interesting, add some African American elements.

What do I mean? Let’s take a basic black solid suit and evolve it across the spectrum of Hip dressing. Although there are a myriad of differences and some genres do blend into other genres, we can see some differences. As a caveat, I am not suggesting that you have to be from one of these groups or walks of life to wear these combinations; I am simply making suggestions to add an element of style to your hip evening out:

Mobster: If European, can be quite sophisticated and revel in the club scene and the idea that  they should wear lighter ties on darker shirts. Charcoal, black or midnight blue shirt with diamond or gold cufflinks.

Secret Agent: Or what I like to call, urban commando. Think Vin Diesel in the movie XXX.  Black or ice blue hand finished mercerized cotton t-shirt.

Smart Set:  Black cashmere turtleneck from the likes of loro piana or Christopher Fisher a black belt from Dunhill and black Chelsea boots with either a gusset or buckle side.

Designers:  White tone on tone shirt with black solid tie. The men in black look with retro brogues or the latest shirt such as a three color (one background and two crisscrossing colors to form the pattern) checked shirt with the checks set on the collar, cuffs and body on their diagonal.

Hollywood:  Either a black silk shirt with a spread collar

African American: Color is important here, a Fuchsia shirt a black belt with a silver buckle and a silver pocket square to hint at the buckle, black Prada shoes, gold watch; maybe a Cartier.

More Rock Star: Versace silk shirt, preferably with some black in the pattern even in outline to pick up the suit. A Versace belt maybe even with the Gorgon head buckle; maybe even a beautiful sterling necklace or pendant from Tateossian or Chrome Hearts.

Hip is all about luxury. Even when patterns and colors are traditional, it is clear to even the most uninterested observer that the clothes are expensive and sumptuously tactile.

Recently, I have been trying to decide what separates Hip outfits from those worn to the office and for the first time I have had trouble distinguishing them. It isn’t because people work less or play less, it is because the two looks are merging. Experimentation with clothes is a powerful force at the moment for American men. London too is undergoing a great deal of trial and error. For the first time ever, men are wearing clothes they want to wear, one foot in the traditional and one foot in the current. That’s why the traditional rules are relatively useless for men who want to dress well and individually.

I realized this partly because my City of London look of boldly striped suit, colorfully striped/checked shirt and contrasting woven tie  is in NYC still considered colorful enough and novel enough to go from the office where men admire it, to social situations where it has enough color, texture and pattern to interest the fairer sex. There still remain some differences between office wear and stepping out, for instance, I might change shoes for Chelsea boots or brown suede lace ups but the future is clearly in the hands of men defining what makes them look good, important and ultimately, Hip.