7 Style Mistakes to Avoid

As a health coach and personal trainer who’s been helping women for over three decades, I can tell you this: confidence isn’t just about how strong you feel—it’s also about how you see yourself when you get dressed each day.

Here’s the truth: losing weight takes time and consistent effort. It’s a process that involves movement, mindset, nutrition, and lifestyle—something I coach women through every day. But let’s be real—sometimes you want to feel better now, not six months from now.

The good news? You don’t have to wait to lose 10 pounds to look 10 pounds lighter.

Just by dressing smarter—choosing modern, flattering silhouettes and knowing how to work with your shape—you can instantly look leaner, stand taller, and feel more confident in your skin. When you love how you look in the mirror, it can be the little boost you need to carry that confidence into every part of your day.

Let’s talk through 7 fashion mistakes midlife women tend to make and I’ll give you easy, stylish updates that will have you feeling and looking fantastic in your clothes – no weight loss required!

PS. You’ll also love these best tops for women over 50 to hide tummy on Amazon!

1. Wearing Clothes That Are Too Baggy

The Mistake: Reaching for oversized tops and bottoms to “hide” your body.

Why It Doesn’t Work: Excess fabric adds bulk and creates a shapeless look that often makes you appear heavier than you are.

Fix It: Don’t be afraid to show a little shape. Choose clothing that follows the lines of your body without clinging. Look for updated pieces like flowy blouses with a defined shoulder seam or structured fabrics that drape well.

A modern blazer over a tank or fitted tee can add polish while creating shape. You want ease—not excess. Think “tailored with comfort.”

• This is my favorite coatigan that literally dresses up any outfit. Cover your bum and wear it with leggings or tighter pants.
• Shop my favorite blazer to spiff up any outfit. It’s long and has a little shape to it.

2. Wearing Unbalanced Outfits

The Mistake: Pairing oversized with oversized—like loose pants and a big oversized tunic.

Why It Doesn’t Work: This drowns your frame and often looks sloppy.

Fix It: Keep proportions in check. If you love wide-leg or relaxed-fit pants (hello, comfort!), balance them with a more tailored top. Try a French tuck (just the front of your shirt tucked in) for an effortlessly modern look.

On the flip side, if you’re wearing a relaxed top or tunic, opt for a straight-leg or subtle bootcut pant that elongates your legs and anchors the look.

3. Clinging to Outdated Denim Styles

The Mistake: Still wearing low-rise jeans or bedazzled back pockets circa 2003.

Why It Doesn’t Work: Older denim styles often cut across the midsection or draw attention in the wrong places, making your body look shorter or wider.

Fix It: Embrace updated denim! Look for mid-to-high rise jeans in a straight leg or bootcut style that hits at or just above the ankle. Dark washes are slimming and versatile, while a raw hem or trouser-style jean can modernize your look instantly.

Leave skinny jeans behind—they’ve had their moment. And the new barrel jean look is not for everyone, it can make you feel wider and frumpy. 

4. Wearing the Wrong Bra

The Mistake: Wearing bras that are old, stretched out, or just plain uncomfortable.

Why It Doesn’t Work: Poor support affects your posture and can make your clothes fit poorly—especially in the chest and midsection. 

Fix It:  A well-fitting bra lifts your chest and defines your silhouette, making your waist appear smaller and your clothing hang better. Look for supportive styles with wide straps, smoothing sides, and comfort features—because you deserve both form and function.

Throw out the old stretched out bras and splurge on a few new ones that don’t hug the back fat. 

Get detailed reviews of all of my favorite in my guide to the most comfortable bras for women over 50 on Amazon!

5. Wearing Dresses Without Strategic Details

The Mistake: Throwing on a long, loose dress and calling it a day.

Why It Doesn’t Work: While comfy, oversized dresses can look like a tent if there’s no visual structure.

Fix It: Go with flowy—but smart. Look for rouching, smocking, or elastic details that provide subtle shaping without clinging. If you love a flowy maxi, try one with a high-low hem or slightly shorter length to show off your legs and keep it light.

Want a little more definition? Try a belt at your natural waist—or even just above it—to break up the fabric and give your shape a boost without squeezing your tummy.

• This is my favorite dress that is flowy but has some design and doesn’t feel like you are wearing a bolt of fabric.
• I love this body con dress that is not too short and has rouching over the tummy to hide your belly, not accentuate it. I own multiple colors!
• This is my favorite dress for a wedding or event that feels elevated but doesn’t hug the midline.

See detailed reviews of my favorite dresses for women over 50 on Amazon to find your favorite!

6. Wearing Shoes That Shorten Your Legs

The Mistake: Choosing heavy, chunky shoes or ankle straps that visually cut off your leg line.

Why It Doesn’t Work: These can make your legs look shorter and your whole outfit feel off-balance.

Fix It: Choose shoes that elongate. A pointed toe (flat or heel!) gives the illusion of longer legs, and nude tones that match your skin tone help extend your silhouette. Love sandals? Go for sleek, minimal straps.

If you need support, look for wedges or platform sneakers—totally on-trend and easier on your joints. Try to avoid big heavy black shoes that anchor your outfit and feel heavy. 

7. Prioritizing Comfort Over Style Every Time

The Mistake: Wearing only leggings and oversized tees day after day.

Why It Doesn’t Work: While comfort is key, overly casual pieces can drag your energy and confidence down.

Fix It: This one is my biggest problem. I wear athletic clothes every day and can get it a rut of feeling sloppy. Don’t ditch comfort—just elevate it! Choose joggers in a soft fabric with a tapered leg or swap your basic tee for a soft knit top with a cute neckline or sleeve detail.

Layer on a lightweight jacket or add a statement earring to make the outfit feel finished. A little style boost goes a long way in how you feel about yourself.

You deserve to feel good in your clothes right now. This isn’t about chasing trends or pretending to be 25—it’s about stepping into your power, honoring your body where it’s at, and letting your style reflect the strong, beautiful woman you are today.

So go ahead and clean out those closet mistakes, try something new, and rediscover the joy in getting dressed. You might be surprised how a few simple changes can help you feel happier, lighter, and more like yourself again.