Dressing For Your Age

Signature Taste, vol 09

This is the weekly paid issue of (In)Decent Taste containing an in-depth lesson to cultivating an exquisite wardrobe while saving you time, money and answering the age old question of “what should I wear today”.

Photo by Jin Kyu Son

Age is opportunity no less than youth itself." - Henry Wadsworth Longfellow

From blue zone diets to red laser therapy, the human world is obsessed with youth, we're constantly bombarded with messages about aging well and healthy living. I’m looking down the barrel of a definitive birthday and so I’ve been thinking about "age-appropriate" clothing.

But what does that really mean? Is there truly a universal standard for how we should dress at 30, 50, or 70? I believe there's something far more powerful than following arbitrary fashion rules based on birth certificates—creating our own personal style constitution that evolves as gracefully as we do.

The term "age-appropriate" often carries restrictive connotations. It suggests limitations rather than possibilities. Instead of focusing on what we shouldn't wear, what if we shifted our attention to developing a signature style that makes us feel confident, comfortable, and authentically ourselves?

True style isn't about conforming to external expectations but about understanding who we are now—our lifestyle, values, body, and how we want to present ourselves to the world. This doesn't mean ignoring conventional wisdom altogether, but rather adapting it to suit our personal narrative.

Let me tell you something they don't want you to know. Age isn't your style liability. It's your greatest asset. And if you’re reading this in your twenties, time is your asset; leverage it wisely.

With age comes discernment. You know quality when you see it. You recognize substance beneath style. You understand the false economy of fast fashion. You've developed the confidence to invest in pieces that will serve you for years rather than weeks.

With age comes perspective. You've seen trends cycle and recycle. You know which ones flatter you and which ones don't deserve a second chance. You understand that style is a marathon, not a sprint.

With age comes authenticity. You've earned the right to dress for yourself rather than for the approval of others. You understand that genuine presence trumps manufactured perfection every single time.

Rather than viewing age as a limitation, consider it your style superpower. With age comes:

• Self-knowledge: You know what works for you and what doesn't

• Confidence: You're less susceptible to fleeting trends

• Discernment: You can invest in quality over quantity

• Authenticity: You understand that genuine style comes from within

A powerful personal rule might be: "I will leverage my years of style experience rather than trying to dress like a younger version of myself."

Write your own standards. Give some thought to those little style standards you live by or want to achieve. I’ll never wear pajamas in public. I’ll never wear a hoodie. I don’t own sweatpants. I’ll always tuck my shirt into trousers. I don’t wear… I do wear…

Define your values. Ask yourself: What do I want my appearance to communicate? Is it sophistication, creativity, playfulness, authority, or perhaps a blend of these qualities? Your clothing is a form of non-verbal communication,decide what message you want to send. For example, you might value comfort but also wish to appear polished in casual settings. This could translate to a personal rule: "I choose well-fitted casual pieces in quality fabrics over athleisure or trends."

Honor your form. Our bodies change throughout life. Rather than lamenting these changes, acknowledge them and dress the body you have today. This might mean:

• Identifying your most confident features and highlighting them

• Understanding which silhouettes make you feel your best

• Choosing fabrics that drape well on your current figure

A personal rule might be: "I prioritize fit over size labels and invest in tailoring when necessary."

Elevate your casual wardrobe. As we mature, how we interpret "casual" often evolves. The graphic tees and ripped jeans that felt right in our 20s might not align with our current lifestyle or comfort level. Consider elevated casual alternatives:

• For resort wear: Linen shirts instead of tourist tees; well-cut shorts rather than baggy board shorts

• For everyday casual: Dark, well-fitted jeans instead of distressed denim; polo shirts over graphic tees

• For athleisure: Coordinated sets rather than mismatched gym clothes

A potential rule: "My casual wear will always include at least one refined element to elevate the look."

Style signature. What’s your signature style? Your go-to? The outfit that is quintessentially you and goes with almost every occasion. That accessory people know you by. The scent that reminds people of you. From signet rings to boater hats, the options are endless. Think of Anna Wintour’s sunglasses or Carolina Herrera’s white shirt. Make something yours.

Here’s the thing about birthdays and reflection, I realize someday I may be elderly scrolling through life’s memories and I’ll see all of my old sartorial friends, hopefully many that are still around. There will be fashion flops and mistakes aplenty but they will have been made in the pursuit of finding myself.

---

You may also like:

---

If you enjoyed what you read today, please click the heart so more people like you can see our work.

As a paid subscriber, you will get weekly in-depth emails featuring tips and tutorials that will:

Save you money in the long run while vastly improving your wardrobe.

Save you time by making buying clothing and dressing effortless and enjoyable.

Eliminate the headaches of a closet full of clothes and nothing to wear.

We do not feature affiliate links. If we do recommend anything, it’s because we honestly believe in it and its value to you. No commission collected.