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How to Do a Wardrobe Makeover, One Piece at a Time

Update your closet with neutrals and must-haves to embrace your style at 50 and beyond


a collage with people modeling outfits and clothing hanging from hangers
(From left) Build a core wardrobe with basics that suit your lifestyle. Options may include items like the Banana Republic Factory Women Forever V-Neck Sweater in Black; Charter Club Women’s 100 % Cashmere Crewneck Cardigan in Natural Camel Combo; Vionic Women’s Klara Ballet Flats in Black Nappa Leather; Gap Women High Rise Double Knit Boot Pants in Terra Brown; J. Jill No-Iron Popover Tunic in White; Loft Leather Bucket Bag in Cognac; and Lane Bryant Long-Sleeve Wide Leg Ribbed Jumpsuit in Maritime Blue.
AARP (Getty Images, 2; Shutterstock; Banana Republic Factory; Macy’s, 2; Gap; J.Jill; Loft; Lane Bryant)

“What are the best wardrobe colors?”

“Do I really need tailored clothes anymore?”

“Will flats be enough for every occasion?”

“My weight fluctuates — can a wardrobe reboot handle that?”

No one buys “forever” clothes anymore. It’s unrealistic to expect your body, your lifestyle and your tastes to remain the same. Anyone who has lost or gained weight, relocated to a different climate, altered their work or relationship status or finally cleaned out their closet will tell you so. It’s not unusual for women with classic style to say their clothes feel “boring,” or for trendy types to start making a beeline for blazers and crisp shirts. How do I know? I’m a fashion editor with a side hustle as a personal shopper for women over 50. Nothing makes them happier than out with the old, in with the new. So how do you begin again? Start here. 

a leopard printed cardigan and a model wearing a brown pleated skirt
(From left) Charter Club Women’s 100 % Cashmere Crewneck Cardigan in Natural Camel Combo; Inspire Chic Women’s Knit Pleated A-line Midi Sweater Skirt in Brown
AARP (Macy’s, Kohl’s)

1. Pick cool or warm neutrals as your base.

Women’s closets tend to be a hodgepodge of colors, styles, sizes, brands, “maybes” (with tags still attached) and lots of stuff that never leaves the hanger. That said, no wardrobe gets a makeover overnight; it’s a gradual thing. You need a plan.

First, choose your favorite neutral colors to create a practical and stylish base. Which ones? Answering two questions does it. Do you prefer cool colors, like black, gray and navy, or warm ones, like brown, beige, camel and olive? Black shoes and bags, or brown/tan? Sounds simplistic, but the answers will guide your “starting-over” wardrobe. Some women ask, “Can’t I mix cool and warm neutrals?” The truth is, stylists and fashion pros often blur the boundaries between cool and warm and incorporate both.

A neutral base is what gives wardrobes a pulled-together look; even if you only wear casual outfits, that doesn’t mean you can’t add a pop or two of color to personalize your neutral base. Just stay consistent with your cool/warm choices. For example, cool reds like cherry and burgundy with a blue undertone, pinks and blues complement cool neutrals, while yellow-based reds like likecorals and earthy greens pair well with warm neutrals.

Take a look at these wardrobe wannabes that come in neutrals warm and cool: J.Jill Fit Waffle-Textured Tunic in Black or Cafe ($85, jjill.com); Inspire Chic Women’s Knit Pleated A-line Midi Sweater Skirt in Gray, Black or Brown ($40, kohls.com); Chico’s Juliet Slim Cropped Flared Ankle Pants in Black or Caramel Apple ($66, chicos.com); and Charter Club Women’s 100% Cashmere Crewneck Cardigan in Natural Camel Combo ($95, macys.com).

a model wearing a brown sweater alongside images of a pair of black trousers, black ballet flats and a navy blue boatneck shirt
(From left) Quince Women Mongolian Cashmere Crewneck Sweater in Brown; Gap Women High Rise Double Knit Boot Pants in Terra Brown; Vionic Women’s Klara Ballet Flats in Black Nappa Leather; Gap Factory Women Stretch Jersey Boatneck T-Shirt in Deep True Navy Blue
AARP (Quince, Gap, Macy’s, Gap Factory)

2. List your must-haves (and never-agains).

Most women say “I have nothing to wear” when their closets are actually stuffed with clothes. Your tastes do change with age, even if your overall look remains the same. Classic types may still love blazers, button-down shirts and shirtdresses, but now they may prefer a knit blazer instead of a sharp structure, relaxed or oversized shirts instead of fitted styles, and midi-length skirts and dresses rather than ones that stop at the knee.

Trendier women may still prefer leather, bold tees and jeans. Only now they prefer stretch leather pants to leather biker jackets, stripes to slogans and straight-leg or flare jeans to skinnies.

My advice: Make a list with two columns. Determine what matters to you now and what doesn’t. To get going, here are six things many of your peers say they want in their wardrobes now:

  • Neck-lengthening boatneck shirts, like the Gap Factory Women Stretch Jersey Boatneck T-Shirt in Dark Heather Grey, Deep True Navy Blue and New Off White($12, gapfactory.com) and the Banana Republic Factory Women Ribbed Boatneck Top in Black, Mocha Latte or Snow Day ($23, bananarepublicfactory.gapfactory.com).
  • Pull-on pants, like Croft & Barrow Women’s Effortless Stretch Pull-On Straight-Leg Pants in Black, Genuine Navy and Cocoa ($26, kohls.com).
  • Stylish, comfy flats for every occasion. Check out Vionic Women’s Klara Ballet Flats in Black Nappa Leather and Brown Nappa Leather ($150, macys.com).
  • Affordable cashmere, such as the popular Quince Women Mongolian Cashmere Crewneck Sweater in Ivory, True Navy, Teak, Charcoal, Brown and Black ($50, quince.com).
  • Sweater-blazers, such as the Nic + Zoe Women’s Plus Knit Blazer in Black Mix ($198, nordstrom.com).
  • Pants and jeans that come in multiple inseam lengths, like Gap Women High Rise Double Knit Boot Pants in Terra Brown or Black ($63, gap.com) in regular, tall and petite lengths.
models wearing a pair of checked pull on pants, a striped yellow shirt and a gray rib knit skirt outfit
(From left) Style & Co Women’s Straight-Leg Ponte-Knit Pants in Hannah Deep Black; Old Navy Women Long-Sleeve Mariner Loose T-Shirt in Green Stripe; Quince Women Mongolian Cashmere Midi Skirt in Heather Gray
AARP (Macy’s, Old Navy, Quince)

3. Invent your own ‘capsule wardrobe.’

This is a stylist’s term for the clothes that form the core of your wardrobe. Think of reinventing them as an opportunity to stop wearing the same old thing in the same old way. Use your current tastes and lifestyle for inspiration. Don’t feel you need to include items that are no longer you.

For example, people who work in fashion almost always include a trench coat, dark-wash jeans, striped button-downs, a black dress and heels as capsule wardrobe musts. That may be fine if you have an urban lifestyle or truly prefer classy, classic clothes. But what if your taste and lifestyle lean more casual? You might prefer a barn jacket, stretchy, knit ponte pants, striped tees, and ballet flats. That’s your capsule wardrobe! Good choices? Many women mention:

  • Ponte knit pants, like the Style & Co Women’s Straight-Leg Ponte-Knit Pants in Deep Black, Hannah Deep Black and Industrial Blue ($50, macys.com).
  • Polished athleisure looks and sweats. Check out the Athleta Forever Fleece 1/4 Zip Sweatshirt in Bone, Fog Gray Heather, Truffle and Black ($99, athleta.gap.com).
  • Striped long-sleeved tees, like the Old Navy Women Long-Sleeve Mariner Loose T-Shirt in Navy Stripe, Green Stripe and Red Stripe ($27, oldnavy.gap.com).
  • For dressier occassions, a pull-on midi skirts, such as the Jessica London Plus Soft Ease Midi Skirt in Creamy Mocha, Chocolate and Black ($44, nordstrom.com) and the Quince Women Mongolian Cashmere Midi Skirt in Teak Brown, Brown, Heather Gray or Black ($100, quince.com), to wear with boots, sandals or ballet flats.

Remember: You’re doing this for yourself, not your Instagram feed or Facebook snaps.

a white button down shirt, a model wearing wide leg jumpsuit and a black pleated midi skirt
(From left) J.Jill No-Iron Popover Tunic in White; Lane Bryant Long-Sleeve Wide Leg Ribbed Jumpsuit in Maritime Blue; Nine West Women’s Brown Faux Leather Pleated Skirt
AARP (J.Jill, Lane Bryant, Kohl’s)

4. Choose only body-positive clothes!

Every woman needs wardrobe pals: figure-friendly clothes that emphasize her assets and de-emphasize her concerns. Unfortunately, most women have closets that are far from body-positive. Instead, they’re crammed with clothes that used to fit, “someday” jeans and unflattering pieces that are too baggy, boxy or shapeless to do them any good. That kind of wardrobe encourages negativity and shopping for shapewear at the crack of dawn.

Start over. Reset your new-wardrobe goals with clothes that have the design chops to quietly enhance your shape. Include tunics like the radiance-boosting J.Jill  No-Iron Popover Tunic in White ($89, jjill.com) to slip over slim, straight pants or jeans; a sophisticated, elastic-waist skirt, like Nine West Women’s Brown Faux Leather Pleated Skirt ($34, kohls.com), to keep below-the-waist issues your secret; and a one-and-done dark-toned jumpsuit, like the Lane Bryant Long-Sleeve Wide Leg Ribbed Jumpsuit in Maritime Blue ($66, lanebryant.com), to slip cleanly over the curviest curves.

And don’t forget your neutral wardrobe basics. Monochromatic dressing is always your ally. Wear a matching or near-matching top and bottoms in your favorite neutrals to create a sleeker silhouette.

two different styles of slip on shoes and two different handbags
(From left) Old Navy Women Loafer Mules in Bourbon; Journee Oreta Women’s Flexible Round Toe Loafers in Leopard Camel; Madewell The Mylie Shoulder Bag in True Black leather; Loft Leather Bucket Bag in Cognac
AARP (Old Navy, Kohl’s, Madewell, Loft)

5. Opt for stress-free shoes and bags.

Shoes and bags are every woman’s favorite wardrobe buy for a really good reason: You get to ignore your weight, shape and size, and dream a little. It’s a chance to fall in love with leopard loafers, like Journee Oreta Women’s Flexible Round Toe Loafers in Leopard Camel ($44, kohls.com), or animal-print flats, like Rothy’s The Daily Ballet Flat in Sable Spot ($99, nordstrom.com), that work with cool and warm neutrals, knowing they will make you smile with every wear. That said, you’re probably wondering if your cool or warm neutral choices from tip No. 1 will limit your shoe options. Not if you don’t want them to!

Mixing neutrals into your accessories — a cool-toned navy outfit with a warm brown bag and shoes, for example — can personalize your look and give it a stylish twist. Coordinating your shoes and bag to match your outfit (black with cool-toned clothes; brown with warm-toned clothes) does give off a pulled-together vibe, which many women say they prefer. Black shoes and bags will always look dressier than brown, and as a bonus, black bags hide stains better and can make a lower-cost bag appear more expensive.

Brown and camel/tan shoes and bags, like the Loft Leather Bucket Bag in Cognac ($84, loft.com) and Old Navy Women Loafer Mules in Bourbon ($26, oldnavy.gap.com), are in sync with a warm-neutral wardrobe, and lighter shades, such as nude, tan and beige, give any outfit a sunny, warm-weather look.

One starting-over goal women often discuss is wearing flats, and only flats. This category is endless and includes embellished ballet flats, slingbacks, breezy mules and metallic sandals (in cool silver and warm gold!) as well as loafers, sneakers and boots. Flats can handle anything from a black-tie affair to a job interview. Women look for features like cushioned insoles, toe boxes with wiggle room for bunions and hammertoes, and soles that prevent slips.

Another wardrobe redo is your bag style and size. Look for hands-free, shoulder-sitting bags, such as Madewell’s The Mylie Shoulder Bag in Dark Carob or Russet Multi Suede and True Black Leather ($228, madewell.com). Alternatively, try a crossbody style, but do your neck, shoulders and posture a favor by reducing the number of items you carry around. You don’t really need a full makeup kit and a full-size dry shampoo on call, do you? Cut half of what you normally pack, and feel the difference.

a camel colored v neck sweater
Banana Republic Factory Women Forever V-Neck Sweater in Camel
AARP (Banana Republic Factory)

6. Reboot your closet with one item per season.

Sounds strict, doesn’t it? However, following the one-in/one-out rule prevents future mistakes, helps you avoid binge-shopping and gives your renovated wardrobe a lift four times a year. This translates as spending more time browsing and researching, and less time handing over your credit card.  

Whether you are scouting bargains and sales online or considering new-for-you looks, let exploring fresh brands and sites encourage unexpected changes. Maybe you’ll find a more flattering V-neck, like the Banana Republic Factory Women Forever V-Neck Sweater in Camel, Black, Preppy Navy ($30, bananarepublicfactory.gapfactory.com) in cotton, to wear year-round; discover a better go-everywhere dress, like the Eloquii Tie Front Oversized Shirt Dress in Barbados Cherry ($77, nordstrom.com), that’ll never go unnoticed in a crowd; or decide to give your classic wardrobe some edge with faux leather pants, like the J.Crew Factory Women Full-length Straight-leg Pant in Faux Leather in Black ($45, factory.jcrew.com). Like everything else in your life, your wardrobe needs to stay current and flexible, and occasionally updated to stay relevant. Start today!

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