How to Wear Jeans with Style and Confidence at 60 and Beyond

A Graceful Approach to Style, Comfort, and Confidence in Denim

Let’s clear up a myth right now: you’re not too old for jeans. At 66, I’ve found that the key to great style is wearing what feels right for your body, your life, and your confidence.

Do I wear jeans every day? No. But I do wear them proudly. And when I want something softer, I reach for comfy knit pants I’ve sewn myself—like the deep green pair I recently made. The point is this: you deserve comfort and confidence, no matter the fabric. ( BTW, you can purchase the snakeskin fabric from my sewing shop.)

Why Jeans Are Still a Smart Choice

1. They’re Timeless and Ageless

A well-fitting pair of jeans never goes out of style. Whether you’re 26 or 66, jeans offer a classic silhouette that works for almost any outfit.

2. They’re Practical and Polished

With the right fit and fabric, jeans are easy to wear and easy to elevate—pair them with a structured jacket or a handmade top, and you’re ready for errands, meet-ups, or dinner out.

3. They Don’t Have to Be Stiff or Restrictive

Modern denim often includes stretch, soft finishes, and mid- or high-rise waistbands that are much more forgiving—and flattering—than the jeans of the past.

What I Wear When I’m Not in Jeans

While I still enjoy wearing jeans, especially when layered with a great jacket, I don’t live in them.

My daily go-to? I’ve made soft knit pants myself, like a recent pair in a deep green stretch knit. I pair them with a cream-colored jersey top and my handmade snakeskin jacket for a polished, comfortable look that moves with me throughout the day.

This outfit gives me the feel of jeans without the restriction, but I still keep a few favorite denim pieces in rotation—especially when I want a more structured look.

Styling Tips for Wearing Jeans at 66 (and Beyond)

Choose mid- or high-rise styles to flatter your waist and lengthen your legs.

Look for stretch denim for ease and comfort.

Dark washes are sleek, slimming, and versatile.

Try bootcut, straight-leg, or slim styles—whatever works with your shape.

Pair jeans with handmade tops, cardigans, or tailored jackets for effortless style

Dress for You, Not for a Number

You’ve earned the freedom to dress on your terms. If you love jeans, wear them. If you love knit pants, sew them. You don’t have to choose between comfort and style—you can have both.

So wear your jeans when you want to. And when you don’t? Slip into something soft that still reflects your creativity and personal style.

After all, fashion is about expressing who you are—not conforming to someone else’s rulebook.