Aging is difficult as is, but when it comes to realizing those skinny jeans aren’t working for you anymore it can be a real heartbreak. With each milestone, men tend to change their fashion sense to be more age appropriate and can transform their style all depending on career, responsibilities, and body type. Clothing and fashion can be a good way to express your “inner age” in a sense of making fashion statements that exhibit maturity, liveliness, and in some cases, just plain style.

There are a few specific phases in life that tend to force a change in personal fashion (a never-ending journey of self discovery) – young rebels, successful twenties/thirties, the middle aged family man, and the classically retired.

Young and Trendy

Younger generations experiment frequently with their style and can change their outfit after a boost of hormones, few months at the gym, or a first job. This inconsistency in fashion allows for the younger generations to catch onto trends such as skinny jeans, pastel and bright colors, or even animal and floral prints. In this stage statement pieces largely drive the focus of fashion. As we know the young and restless can be rebellion at times and in no way does that stop at style.

Depending on hobbies, activities, friend groups, and drug use, a young man’s style is generally lead by his confidence and, of course,the all mighty wallet. Some like to shock, others prefer to be comfortable and ready to work out at all times. The variety of goth, preppy, boho, sporty, punk, you name it – they rock it.

Suave Success


Twenties to thirties is where you maybe get your first taste of luxury – whether it be a nice watch or some dress shoes, men start to figure out how they want to be presented professionally. This look and successful vibe tends to stick when it comes to casual wear as well. Maybe you pick up golf or start attending a country club changing your style to button downs, polo shirts and loafers. In this stage of fashion, brands and luxury items tend to be the biggest focus in style.

The importance of self-presentation begins to create a sophisticated style placing importance on accessories. No longer is there a need to follow the latest trends or try to shock the parental with a new piercing or hair color. The professional look begins to inspire outfits in all aspect of life such as dinner dates, bars, or even the club scene. The polo shirt tends to become a staple as it can go from the office to the bar and looks great casual or dressed up with a watch and slacks.

Middle of the Road

At this point in a man’s life there may be a significant other, children, pets, and a number of other responsibilities. At this point there is likely a specific brand and style that always fits well and is trustworthy for a nice shirt. Luxurious items are a thing that appears only around Christmas and birthdays, but not to worry, as there is a nice collection built up from the years. Basics take on a strong role becoming a focus at this stage.

By middle age most men have at least one good suite, nice pair of shoes, a solid watch, classy belt, and maybe even some cuff links. Running around from work to daycare to sports to home tends to put fashion in the backseat. Having a nice comfortable pair of jeans versus the trendy or brand name jeans might mean you start buying clothes at Costco while shopping for diapers and dog food. Much of fashion is now determined by gifts with a few exquisite items for those “big birthdays”. Neutral colors take on an important role as they match with most of the closet already.


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After years of work and family, retirement brings on a whole new purpose and need for clothing and style. At this point generally a solid look is clear with a change from the busy business man to the relaxed life of the retired. Most of the fashion at a later age is based on what has been working for years. At this point there is likely a color pallet that dictates personal fashion and style, as well as a healthy collection of gifts regarding what others think you would look nice in. In this stage quality and comfort are the most important aspect of style.

Occasionally an old trend will make its way back into fashion such as a pocket watch, suspenders, or scarfs. The Wiseman has less responsibility making their fashion style one of the most flexible – t-shirts, polo shirt, dress shirt, sweater, jeans, slacks, etc. Bright colors and patterns find their way back in through ties and socks adding some pop to the neutral closet.

The Rest

Of course clothes, shoes, and accessories are not the only way to dress your age – hairstyle and facial hair can also be configured to give off a certain desired fashion sense. A nice clean-cut face gives off a younger vibe allowing for some flexibility with trends and experimentation with colors and patterns. A five o’clock shadow or some nicely groomed facial hair presents a more mature look. For more ideas on facial hair and grooming techniques please take a look at:


As a general rule it is sometimes better to dress above your age versus below. A Wiseman in a bright-colored suite and leopard shoes may come off as being ready for some assisted living. On the other hand a young man dressed in a tweed blazer with brown slacks and suspenders is seen as fashion forward. No matter what stage of life you are in there is always the basics that will create a wearable and classic look. Feel free to experiment with the latest trends – of course in reality everyone has their own style and express them through fashion – wear what you want and work it.