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Starting a Wardrobe Over From Scratch at 50+

Don’t just purge, create a new clothing strategy


spinner image a woman with her hands on her hips looking into her closet
Guerilla/Getty Images

If your first thought is, “C’mon who really does this?” The answer is: plenty of people. Anyone who has lost or gained weight, relocated to a different climate, changed their lifestyle or work situation, is dating again or for whatever reason just cleaned out their closet and said, “What now?” That’s who! As a fashion editor and wardrobe consultant/personal shopper, I know how diverse women’s needs, tastes and daily lives are at 50 and older, but there’s a practical strategy that works for all. Here’s how to gradually create a more body-enhancing, style-boosting wardrobe that makes sense for your life.

spinner image Chico’s Faux Leather Blazer in Black; Old Navy High-Waisted Wow Boot-Cut Pants for Women in Black Jack; Loft Relaxed Pocket Sweater Blazer in Perfect Camel; Everlane The Dream Pant in Heather Auburn
(Left to right) Chico’s Faux Leather Blazer in Black ($169, chicos.com); Old Navy High-Waisted Wow Boot-Cut Pants for Women in Black Jack ($30, oldnavy.gap.com); Loft Relaxed Pocket Sweater Blazer in Perfect Camel ($51, loft.com); Everlane The Dream Pant in Heather Auburn ($88, everlane.com)
Chico's; Old Navy; Loft; Everlane

1. Pick cool or warm neutrals as your base

Do you really prefer cool-toned neutrals like black, gray and navy or warm spicy ones like beige, brown, tan and olive? Black bags and shoes or brown/tan ones? Combining cool and warm neutrals does work, for example a beige blazer with black pants and loafers, or a navy sweater and blue jeans with brown shoes and bag (very French, FYI), but choosing your core neutrals in one direction or the other will improve your wardrobe’s mix-and-matchability. It also gives low-cost clothes and casual outfits a more elevated, pulled together look. To help you make that decision, know that blue denim, chambray and white work with both cool and warm neutrals. Add prints and vary the textures of the pieces to help create a more personalized wardrobe. Finding fresh updates will never be a problem since all neutrals are always in style.

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spinner image Liz Claiborne-Plus Alexis Women’s Mid Rise Straight Pull-On Pants in Charcoal Heather; H&M Turtleneck Dress in Beige Melange; Fantaslook Women’s Fall Long Sleeve Tunic T-Shirts in Khaki and Black; Talbot’s No-Iron Perfect Shirt in Flecked Animal in White/Dark Walnut
(Left to right) Liz Claiborne-Plus Alexis Women’s Mid Rise Straight Pull-On Pants in Charcoal Heather ($34, jcpenney.com); H&M Turtleneck Dress in Beige Melange ($60, www2.hm.com/en_us); Fantaslook Women’s Fall Long Sleeve Tunic T-Shirts in Khaki ($17, walmart.com); Talbot’s No-Iron Perfect Shirt in Flecked Animal in White/Dark Walnut ($100, talbots.com)
JCPenney; H&M; Walmart; Talbots

2. Make a list of comfort must-haves

Many women have closets full of past-life clothes and say they have nothing to wear. Start over by listing the clothing details that matter to you now. Do you prefer elastic waistbands and pull-on pants and dresses? Midi hemlines instead of knee-length? Longer relaxed tees and tunic-length sweaters? Want easy-care clothes that don’t require ironing or dry-cleaning? All these demands aren’t unreasonable and they’re available everywhere from pricey designers like The Row to fast-fashion brands like H&M and Zara and mass market retailers like Target and Walmart. This time around, be more selective about details and don’t back down when other choices are on sale.

spinner image J. Jill Sonoma Houndstooth Duster in Dark Oatmeal Multi; Banana Republic Pia Denim Midi Skirt in Dark Wash; Abercrombie Collarless Tweed Jacket in Navy; Ilse Jacobsen Rain Slicker in Dark Shadow
(Left to right) J. Jill Sonoma Houndstooth Duster in Dark Oatmeal Multi ($149, jjill.com); Banana Republic Pia Denim Midi Skirt in Dark Wash ($160, bananarepublic.gap.com); Abercrombie Collarless Tweed Jacket in Navy ($140, abercrombie.com); Ilse Jacobsen Rain Slicker in Dark Shadow ($189, nordstrom.com)
J. Jill; Banana Republic; Abercrombie & Fitch; Nordstrom

3. Invent a “capsule wardrobe” for your real life 

This is a chance to stop wearing the same old thing. You’ve probably heard the term “capsule wardrobe.” It’s basically an edited group of items selected to make dressing well foolproof. The list often includes iconic pieces like a trench coat, a blazer, tailored pants and dark wash straight-leg jeans. You get the idea. It’s a stylish urban-leaning wardrobe for those who love classic clothes. But what if you prefer more casual clothes or want a little more edge or glamour to your look? Your capsule wardrobe may be different and include a duster, a hooded rain coat, a cropped tweed jacket or a denim midi skirt. Make the wardrobe turnover slowly; no need to toss all and buy everything new at once. Start with three updated basics that respect your comfort must-haves — and build from there. Remember, you’re dressing for you, not the next issue of Vogue!

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spinner image Ann Taylor Ribbed Relaxed Mock Neck Sweater in Cafe Au Lait; Mango Print Wrap Dress in Black-Plus; Spanx The Perfect Pant, Kick Flare in Basic Black; Dokotoo Women’s Pullover Sweater Casual Relaxed Fit Turtleneck Striped Sweater in Khaki
(Left to right) Ann Taylor Ribbed Relaxed Mock Neck Sweater in Cafe Au Lait ($98, anntaylor.com); Mango Print Wrap Dress in Black-Plus ($70, mango.com/us); Spanx The Perfect Pant, Kick Flare in Basic Black ($148, spanx.com); Dokotoo Women’s Pullover Sweater Casual Relaxed Fit Turtleneck Striped Sweater in Khaki ($34, walmart.com)
Ann Taylor; Mango; Spanx; Walmart

4. Emphasize body-positive clothes

Let’s be clear. Body positivity means selecting clothes that make you feel great about your shape and size. As you reset your wardrobe, play more with proportions and use pieces with volume where curves and extra pounds need room to flourish. Try contrasting proportions by wearing roomy tops and slouchy or wide sweaters over slim pants or kick flares. Pair pleated or A-line skirts with fitted tops for contrast, or amp up the volume on top too with boxy cropped sweaters and shirts that just cover the waistband. Invest in curve-celebrating wrap dresses that honor an hourglass silhouette and freedom from scales. And here’s a bonus that’s built into your wardrobe: Wear your neutrals head-to-toe for a monochromatic effect and instantly appear taller and sleeker without the need for heels or shapewear.

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spinner image Journee Collection Women’s Celina Kitten Heel Loafer Square Toe Pumps in Brown; Vince Camuto Maecy Leather Convertible Hobo Bag in Warm Caramel Cow; A New Day Women’s Laurel Loafer Flats in Black; & Other Stories Braided Leather Shoulder Bag in Grey
(Left to right) Journee Collection Women’s Celina Kitten Heel Loafer Square Toe Pumps in Brown ($60, walmart.com); Vince Camuto Maecy Leather Convertible Hobo Bag in Warm Caramel Cow ($198, nordstrom.com); A New Day Women’s Laurel Loafer Flats in Black ($33, target.com); & Other Stories Braided Leather Shoulder Bag in Grey ($259, stories.com)
Walmart; Nordstrom; Target; & Other Stories

5. Redefine your bag and shoes

Count accessories in when rethinking your current likes and dislikes. Want to wear flats 24/7? Buy only shoes you can walk, run, drive and dance in without feeling like you’d better bring a pair of sneakers along, unless of course your favorite flats are sneakers. Make grounded loafers, refined ballet flats, flat boots and booties your besties, and if you still want heels, opt for versatile loafer-pumps … with cushioned insoles this time around. Fed up carrying heavy bags that stress your hands, neck or shoulders, and totes so spacious they make finding your keys or wallet feel like a treasure hunt? Get a lighter shoulder bag that works with your chosen neutrals. Textured finishes like woven or pebble-grained faux leather show less dirt than light ones. And do your bag and body a favor and eliminate half of what you carry.

spinner image Worthington Short Sleeve Midi Sweater Dress in Yellow Sulphur; Eloquii Elements Women’s Plus Pleated Faux Leather Skirt in Black Onyx; J. Crew Cashmere Relaxed V-Neck Sweater in Neon Fuchsia
(Left to right) Worthington Short Sleeve Midi Sweater Dress in Yellow Sulphur ($80, jcpenney.com); Eloquii Elements Women’s Plus Pleated Faux Leather Skirt in Black Onyx ($40, walmart.com); J. Crew Cashmere Relaxed V-Neck Sweater in Neon Fuchsia ($158, jcrew.com)
JCPenney; Walmart; J. Crew

6. Satisfy trend cravings with one item a season

This will prevent you from an off-the-track buying binge and making mistakes again, and it also lets you crank up the fun risk-free. Some women follow the one-in-one-out rule each time they add a wow item and delete something that no longer works. This progressive turnover can help you ease into a new-for-you look and enable you to take some chances on pops of color to accent your neutrals. Even the most classic wardrobes need a dare-to-wear opportunity to keep from going stale.

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