Styling Wisdom: What I’ve Learned About Fashion After Two Decades

After twenty years as a stylist, I’ve had my fair share of fashion adventures. Some outfits have been absolute gems, while others—let’s just say—should have stayed on the rack. Given my extensive experience dressing women, I have come to realize what I absolutely won’t be wearing anymore. Grab a seat, because I’m ready to share the insights I’ve gathered over the years.

The Importance of Authentic Choices

As I age, I’ve become increasingly honest with myself about what truly works for my lifestyle versus what merely looks good in a well-lit dressing room or on social media. My editing process has become more ruthless; I’m no longer engaged in battles that don’t favor me. Below, you’ll find my personal list of clothing items I’ll avoid, but if they happen to be your favorites, feel free to disregard my opinion entirely.

Why I Don’t Wear Capri Pants

Capri pants and I have a long history, and it’s one that has increasingly soured over the years. The tricky thing about capris is where they hit on the leg. Most capris land right at the widest part of the calf, which ends up making one’s leg appear broader. This break suspends the natural line of the leg, often creating an awkward, shortened silhouette.

Flattering pants, crops, and skirts typically end where the leg narrows—above the ankle or at full length. A cropped pant that finishes slightly above the ankle has a cleaner line, elongating the leg instead of cutting it off at its widest.

Even pedal pushers, which seem to offer a solution by hitting below the knee, can still present challenges. The cut often makes the thighs appear wider, creating an unflattering horizontal line where the eye perceives the bottom of the thigh. Footwear choice becomes crucial with this style; a flat shoe can ruin the length and make legs look stumpy, while a heel or pointed toe can narrow the silhouette but might limit versatility.

Ditching Leggings (Even for Pilates)

Leggings have taken the world by storm with their comfort and ease, but they’ve never been my go-to. As I age, I find myself less inclined to wear leggings in public. Quite frankly, leggings don’t leave much to the imagination, and I’ve reached a point where I prefer outfits that offer a bit more coverage and structure.

Even for Pilates—a classic legging-friendly environment—I opt for joggers. They provide the same ease of movement but allow me to dodge the anxiety of wondering how I look while bending over. Plenty of women rock leggings beautifully, and I applaud them, but I’ve simply made peace with the fact that they don’t suit me.

Embracing Natural Fibers

In my two decades of fashion experimentation, I’ve fallen victim to the allure of cheap acrylic and polyester garments far too many times. Each time I made that budget-friendly purchase, I inevitably regretted it. Those fabrics can trap heat, cling in the wrong places, and lose their shape quicker than you can say “wardrobe malfunction.”

These days, I prioritize natural fibers: cotton, linen, wool, and cashmere. These fabrics breathe well and fall more naturally on the body. While I occasionally incorporate blends, I no longer succumb to the temptation of cheap materials just because they come in a cute cut.

Growing older has surprisingly simplified my dressing process. I no longer force myself into clothing that just doesn’t feel like me; instead, I focus on fit, fabric, and practicality—essentially what supports my current lifestyle, rather than the one I envisioned when I bought the piece.

Understanding What Works for You

Each item on my ‘no’ list fails for a consistent reason: they work against my body rather than enhancing it. Capri pants end at the widest point, leggings expose too much, and cheap fabrics fight against my body shape. When clothing doesn’t flatter, it’s easy to turn that frustration inward, but once I understood that the issue often lies with the garment, it changed everything about how I shopped.

Armed with this knowledge, I walked into stores differently. I stopped convincing myself to buy items that were never going to work. Instead, I began selecting pieces that truly complemented my figure and style.

As you curate your wardrobe, remember that your clothes should work for you. They should empower you, freeing your mind to think about the more important things in life rather than worrying about your outfit shifting when you sit down.

Each of our lists will look different, reflecting our unique experiences and preferences, and that’s beautiful. I encourage you to wear what resonates with you and boosts your confidence.

I’m curious: what’s on your ‘never-wear’ list?