THIS POST MAY CONTAIN REFERRAL LINKS. IF YOU CLICK THROUGH AND TAKE ACTION, I MAY BE COMPENSATED, AT NO ADDITIONAL COST TO YOU.
I want to begin this guide to fashion over 50 with an important point: if wearing bold prints, miniskirts, red cowboy boots, or glittery angel wings makes you incandescently happy, wear them. Don’t let anyone talk you out of what brings you joy. The best part of dressing well after fifty is that it’s on your terms.
One of my favorite fictional characters is Mary Dell Templeton, the heroine of Between Heaven and Texas and From Here to Home. Mary Dell’s taste might be questionable—she’d admit she has “no more taste than a hothouse tomato”—but she likes how she looks. That confidence is what matters. I’m not here to talk anyone out of choices that make them feel good.
Still, many readers have asked for practical advice about dressing well after fifty, so here are the principles that have guided me.
Early on my approach to shopping was simple: if it fit and looked good on the hanger, I bought it. That changed when I started doing book tours with TV interviews and photos. Seeing an unflattering outfit plastered across social media will quickly sharpen your sense of what works on camera and in real life.
Those experiences shaped my current fashion philosophy for women over 50: simplicity is always in style.
CLASSIC STYLE
One of the best advantages of being over fifty is experience. You now recognize trends and know many won’t last. “Flash fashion” may be cheap, but if you wear a $10 top only a couple times before it falls apart or goes out of style, it wasn’t a bargain. Invest in a well-tailored, higher-quality piece you’ll wear repeatedly for years—this delivers far better value.
A smart trick for buying investment pieces on a budget is to shop end-of-season sales for classic garments. If you find a timeless jacket or coat you love, buy it and save it for the next season. Because it’s classic, it will still look fresh when you wear it again.
MIX AND MATCH BASICS
Build your wardrobe on well-constructed basics in excellent fabrics that mix and match. These foundation pieces create a sophisticated, flexible wardrobe suitable for travel, events, and everyday life.
Consider two versatile jackets, two pairs of tailored trousers, two sweaters, three crisp cotton blouses, a simple solid dress, and a skirt that moves easily from day to night. Those few pieces can be combined in many ways to create polished looks—I’ve done it on a six-week book tour.
SOLIDS
As an avid quilter I adore patterns, but for fashion over fifty solids are usually the safer choice. That doesn’t mean you must avoid patterns—small-scale, subtle patterns like tiny checks, tweed, or small plaids can add interest without overwhelming. Large, busy prints tend to draw attention to areas you might prefer to downplay.
If you choose a bolder print—buffalo plaid, large florals, or an embroidered jacket—keep everything else simple. Aim for a classic, timeless, and sophisticated look. Dressing mostly in a single color or tonal palette creates a long, lean line and a polished appearance. If you want more color, introduce it with a jacket, vest, or shawl in a complementary hue.
LAYERS
Layering is a powerful styling tool for women over fifty. My closet is full of jackets, capes, shawls, and vests that add interest while creating a long, flattering silhouette from the shoulders down. Proper layering draws the eye and helps conceal areas you prefer not to emphasize, producing a refined, put-together look.
Be careful not to overdo it: too many heavy layers can look bulky and sloppy. Usually two layers are enough, with the outer layer made of a lightweight, fluid fabric. A classic, fail-safe combination is a white blouse under a v-neck sweater topped with a jean jacket—casual, comfortable, and timeless.
FIT THAT’S JUST RIGHT
Resist the urge to hide behind oversized, shapeless clothing. Voluminous, ill-fitting garments can make you appear larger, not slimmer. At the same time, clothing that is too tight will emphasize areas you might prefer to soften. In the dressing room, aim for a Goldilocks fit: not too tight, not too loose—just right.
ONE FABULOUS ACCESSORY
After you’ve assembled a classic outfit—mostly solids, simple patterns, and a flattering jacket—add one standout accessory. This should be the focal point: the piece that people notice first and that earns you compliments.
Accessories let your personality shine and are an excellent place to balance creativity and budget. A lavish handbag, a silk scarf, chandelier earrings, a statement necklace, or bold shoes can transform a simple outfit. Accessories don’t need to be expensive to be effective: some of my most complimented pieces were inexpensive finds like a gold cuff or discounted floral pumps.
Search sale bins, consignment shops, flea markets, and craft fairs for unique accents that won’t break the bank but will make your look memorable.
TWO IRONCLAD RULES
While many aspects of style are flexible, I hold firmly to two nonnegotiable rules:
1) No matter how deep the discount or how famous the designer, if you don’t love it, don’t buy it.
2) The most beautiful thing a woman can wear at any age is confidence. If an outfit makes you feel confident, that’s the outfit you should wear.
And don’t let anyone tell you otherwise. Not even me.
