The Wrong Question

When out shopping in retail stores, you may have heard this question asked by fellow patrons, you may have been asked by a friend, or perhaps you have even uttered these words yourself: “Am I too old for this?”  Please stop! It’s the wrong question. 

Age should have nothing to do with your style choices, and nothing to do with your personal or professional image. Instead, the relationship between age and style should be open and exciting – we all look different regardless of age, and we all lead different lives.  

Theoretically this sounds reasonable, yet how is someone – of any age – to make style choices in a sea of cropped pants, crop tops, and lots of leather?  By asking the right questions:

  1. Does this make me happy? Whatever the item may be, when you put it on, does it literally make you smile? Do you feel so good that you want to escape from the confines of the dressing room to strut your stuff? If you answer ‘yes’ with confidence, it’s time to move on to question #2…if the answer is no, trust your gut and move on! You need not embrace every trend that comes along.
  2. Does this look good on me? Does the item show off your best assets, or does it draw attention to something that you would rather downplay? Does the color brighten your complexion, or does it wash you out? If you have trouble being objective with yourself, ask a friend or spouse for an unbiased opinion. It is not always easy to separate what you like versus what looks good on you.  
  3. Does this fit me properly? Fit is one of the most important aspects of being well-dressed. Even if you love something, if the fit is off, let it go or take it to a reputable tailor. And it isn’t only ‘too tight’ clothing that are mistakes – baggy pants (unless intentional), and wide, sloppy sleeves are equally unattractive. Whether a businessman or businesswoman, there is nothing that destroys your credibility like an ill-fitting suit. 
  4. Will this be appropriate for my lifestyle?  Do you intend to wear this in an office setting, or just for play?  Keep in mind that at work you should pay attention to dress codes as well as the image that you want to project. Outside of work, this is when you can express yourself freely, regardless of age and/or regardless of what others are wearing. 

Let’s explore two examples: 

In an article in the WSJ, Dale Hrabi, the over-50 Lifestyle Editor, decided to explore the millennial trend of men’s cropped pants, complete with photos of various options/brands that he tried. [Sept 29, 2022] These fashion-forward pants may not be seen in the streets of Boston, but Manhattan was a different story. Some he liked, others not so much, which makes perfect sense since we all have our personal preferences. Seeing a fashion trend on a younger generation may pique our interest, yet whether we embrace it ourselves should be just that – personal preference, unrelated to age.

Now switching gears to women, and the trend of crop tops! There are many over-50 gals on social media, myself included, that enjoy wearing crop tops and encourage the ‘no age rule’ regarding this trend. While I stand by my point that style has no age barriers, it does take attention to detail to look classy when opting for certain styles. If you wear a crop top with very low-rise jeans and six inches of skin showing, that’s trashy at any age. Balance a crop top with a high-waisted, more conservative bottom for a look that’s plenty badass, but still shows class. The point here: it’s not the age of the woman that makes it look bad; it’s how it is worn. 

Style need not fade with age. Just as other aspects of ourselves become more pronounced, so can our personal style. We only have to ask the right questions. 


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  • I completely agree, I recently purchased a faux leather dress that was too short for my comfort level, but when paired with black tights and knee hi boots, it looked fantastic and I felt amazing! Watching you has helped me be a little bit more daring as I was when I was younger, now I am 58 and doing my best to always put my best self forward❤️

    • That is so great! It also depends on where you are going – maybe you could be more riské (skip the tights) on date night??? 😉
      Thanks for your comment!



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