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10 Must-Have Wardrobe Items for Women at 50+

Here’s how to look current, cool and confident

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By the time we hit 50, most of us could benefit from a wardrobe refresh.

Our bodies, faces and lifestyles have changed over the decades; however, our style choices haven’t always kept up.

Do we need hard-core rules? Actress Ellen Barkin, 68, famously declared in O, The Oprah Magazine that women over 50 should never wear blue jeans to dinner. I (and my uber cool Mother jeans) beg to differ.

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Forget those outdated rules! We just need a few easy-to-follow guidelines to great style and answers about how to get it.

Below is a master list of go-to pieces for women who want to fight the frump and look smart, energetic, modern and, yes, sure ... appropriate. Consider these investment pieces that you will wear for many years to come, because they will never really go out of style. View them as your foundation and build from there. You can wear these basics to work, out to dinner and anywhere else:

1. Dark denim, mid-rise, boot-cut jeans

The boot-cut hem leaves room for booties (also called “ankle boots”), which are the perfect footwear option for almost every occasion. (Best booties are from Stuart Weitzman, Cole Haan, Sam Edelman, Madewell and, for sheer comfort at a good price, Vionic). You can tuck boot-cut jeans into tall boots, too. This style is the perfect look for women over 50 because they balance out the silhouette — not too tight, not too loose, but just right.

Tip: Keep length about an eighth of an inch off the floor (depending on the shoe), and make sure the jeans fit well (with a little stretch) in butt and hips. Take the waist in, if necessary. Favorite options include Mother, Levi’s, Madewell, and believe it or not, Spanx has great-fitting jeans, too.

2. Dark denim, mid-rise, straight-leg jeans

Skip the tight skinny jeans (unflattering on most of us), and get these in dark blue, with no fading or whiskering and definitely not distressed. Pair with flat loafers or low block heels with squared toe (on trend) and tuck them into tall boots (even over the knee) in cooler weather. As with everything else, booties also work perfectly (see above for our favorites).

Tip: Straight-leg jeans go perfectly with longer jackets or tunic tops. Check out options from Uniqlo, 7 For All Mankind, J Brand, Levi's, Mother, Agolde or Spanx. Prices start at $75.

3. White jeans (boot-cut or straight-leg)

In warmer weather, wear with wedge sandals and tunic tops or a white tank with a crisp navy jacket or denim jacket to pull the look together. When it gets cooler, pair with brown or black booties, a sweater or jacket (a leather moto jacket, see details below) and a pretty scarf in colors that flatter your face.

Tip: Be sure to wear underwear that matches your skin color with any white pants.

4. Great-fitting pants

Look for high-waisted pants in a lightweight wool blend (wool/Lycra is best) in black, charcoal or navy (or a pair in each color) that you can wear all year long. The cut of the pants is crucial, and the length must be exact. Take your shoes and booties to the store (and to the tailor, if necessary) to get a perfect fit.

Tip: Wear with a silky blouse, a T-shirt or a tank with a cardigan or jacket. Some great options are by Theory, J. Crew, Spanx, Everlane and Ann Taylor. Prices start at about $60.

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5. Black blazer

A black blazer in a light wool/lycra blend is one of the most versatile pieces you will own (but consider navy, too). Wear it with jeans, skirts, dresses, pants — it will elevate everything. Make sure it fits your shoulders exactly, can button in the front (even if you never wear it buttoned), and sleeves should hit slightly below your wrist. It should fall below your hips. Take it to the tailor (your new best friend) to create the perfect fit.

Tip: Wear tanks, black or white tees (check out tees from Target) and jewel-colored blouses underneath. Some blazers to try are from Theory, Norma Kamali (love the stretchy spandex/lycra blend), J. Crew and Target. Prices start at about $120.

6. Black pencil skirt

Versatile, stylish and surprisingly flattering, no matter what your size. Wear it to the knee (or slightly shorter if worn with black tights). Make sure it has a little stretch and is fitted, but not too tight. The best look for us is to pair with black tights and booties. Steer clear of flat shoes. Go with a mid-heel or high-heel pump (squarish toes with block heels in suede or nubuck are perfect), high boots (but not over the knee) and booties.

Tip: A black blazer could look severe with this skirt; instead, balance the look with a shorter multicolored jacket with a solid color T-shirt underneath or a flowy, silky blouse tucked in. The best-fitting pencil skirts I’ve found are from Spanx, Theory, J. Crew and Banana Republic. Prices start at about $120, but shop around.

7. Sweaters

These are a year-round fashion accessory and the best way to cover up arms that are less than toned. Look for long and three-quarter-length sleeves that hit you at or above the hip. Longer sweaters are great with straight-leg jeans or pants, but not with skirts. The most versatile sweaters are well-fitting but not too tight and fall around the hips. Look for nonbulky options in cashmere and cotton blends. You should be able to wear these all year long, even under your cool black blazer or with your new jeans. Some of the nicest sweaters are from Madewell, Banana Republic, Gap, Goodthreads (on Amazon), Zara and H&M, starting at $45.

Tip: Take a look at button-down cardigans, too, to wear instead of a blazer. Get a size or two smaller than usual, or you’ll end up with a “Mumsy” sweater, which can look frumpy. Cardigans should be snug, and never wear it closed: The point of sweaters and cardigans is to cover your arms and add a pop of color to your outfit.

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8. Tank tops

Buy these staples in bulk, once you find the ones you like best. Get them in white, black and cream to wear under all your new cardigans, jackets, blouses and sweaters. I wear them under almost everything for a smoother look.

Tip: The fit should be snug, so size down if necessary, and make sure they’re long enough to tuck in and stay put. Uniqlo, Target, Gap and Spanx all have great tanks. Prices start at about $10.

9. Dresses

Dresses make everyone feel pretty and sexy, and there are three styles that flatter women over 50 best, no matter our size or shape:

  • Wrap dresses, especially those with long or three-quarter-length sleeves — knot the belt on the side, never in front, and do not tie it in a bow!
  • Sleeveless sheath dresses worn with snug-fitting cardigans or jackets, which are perfect for almost any occasion.
  • “Fit-and-flare” dresses that are fitted on top and flare out slightly starting at the waist, creating a flirty, swingy look.
  • Jewel colors look good on all skin tones; keep length at the knee or slightly above.

Tip: Have at least one perfectly fitting LBD (little black dress) in any of these styles, which can be dressed up or down. Great-fitting dresses can be found at Target, Diane von Furstenberg, Theory, Nicole Miller, Hugo Boss, M.M.LaFleur, Ann Taylor and Amazon at all price points.

10. Classic black leather moto jacket

No, a black leather jacket is definitely not too young for women over 50. Wear it with everything you own: jeans (very cool with white jeans), skirts and dresses. A black leather jacket looks particularly alluring over a flowery, flowing midi dress. This staple is more expensive than the others, so shop around for one that fits right (cropped at the waist is best) and is classic-looking, so you can wear it forever. Shop in stores for this investment piece, instead of online. It might be best to go to high-end department stores to get a wider range of labels to try. Some options to look for are Rag & Bone, Madewell and Club Monaco.

Tip: You can get the moto jacket look without the leather. Instead look for faux or vegan leather jackets from BlankNYC and Free People.

You can mix and match all these pieces, depending on the occasion, for different looks. Add a few accessories — a statement necklace (chunky, worn close to the neckline), colorful scarf, cuff bracelet, perfect shoes and beautiful bag (clutch for evenings and classic black leather over-the-shoulder for day ) — and you’re ready to go.

Style Smarts

  • Get a good tailor. Clothes look best when they fit well.
  • Define your waist, no matter how big or small.
  • Keep your skirt and dress lengths to the knee or slightly above.
  • Flowy dresses look best if they are mid-calf length.
  • Steer clear of cropped pants — they were an unflattering fashion fad for way too long.
  • Don't show too much skin: too-short skirts and tops that are too low don't flatter anyone.
  • Keep it simple; stay away from too much bling.
  • Mute the loud prints, lean toward solids, especially jewel tones.
  • Buy bras that really fit (get fitted by a pro once a year) and consider “shapewear” when needed.

Editor’s note: This article was published Sept. 25, 2013. It has been updated with new items and information.

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