10 New Ways to Dress for Work Now

Fashion finds to wear to every kind of workplace, from traditional to dress-casual

by Lois Joy Johnson, AARP, November 11, 2021

A woman using a laptop while working in an office

Westend61/Getty Images

Working from home spoiled us. Wasn’t it great to not think about a daily work outfit at 7 a.m.? Those of us with online Zoom meetings learned to do the half-and-half thing … and still do! Waist up we’re all polished top, jewelry and makeup, waist down we’re in sweats and slippers. But now it’s back to business. Whether you work in a traditional office or cubicle, an open-plan situation, a store or call on clients in person, know that work clothes have had a mini makeover. Here are 10 ways to dial up your 9-to-5 style:

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Photos

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PHOTO BY: Macy's; Target (2)

(Left to right) Avenue Plus Size Super Stretch Bootcut Average Pants in Black; Who What Wear Women’s Turtleneck Pullover in Brown; A New Day Women’s Ellie Chelsea Boots

1. Black boot-cut + turtleneck + ankle boots

If you love a quick sophisticated look, get a pair of black tailored flare pants — the new must-have work basic. Choose an update like the Avenue Plus Size Super Stretch Bootcut Average Pants in Black ($55, macys.com) and pair it with ankle boots like the A New Day Women’s Ellie Chelsea Boots ($30, target.com) and a highneck sweater like the Who What Wear Women’s Turtleneck Pullover in Brown ($35, target.com). The mix of black and brown is new, too, and really opens up your choices from pieces already in your closet.
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PHOTO BY: Anthropologie; Gap; DSW

(Left to right) Avec Les Filles Longline Plaid Blazer; Gap High Rise Vintage Slim Jeans with Washwell in Dark Indigo; Franco Sarto Carol 2 Loafer in Black

2. An oversize blazer + dark high-rise jeans + chunky loafers

This is an update to our throwback dress-casual formula. Instead of oldies with big padded shoulders and low-rise jeans, try a longer blazer like the Avec Les Filles Longline Plaid Blazer in Red Motif ($148, anthropologie.com), high-rise jeans like Gap High Rise Vintage Slim Jeans with Washwell in Dark Indigo ($70, gap.com) and lug-sole loafers like the Franco Sarto Carol 2 Loafer in Black ($119, dsw.com/en/us). You might even make things easy and wear variations of this look five days a week. P.S. The trick in every one of the 10 looks in this work-wear column is to include at least one trendy-ish item.
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PHOTO BY: Madewell; Gap; DSW

(Left to right) Madewell Twill Drawstring Jogger Pants; Gap Cozy Half-Zip Sweater in Stone Beige; Naturalizer Marianne Slip-On Sneaker–Women’s in Tan Embossed Leather

3. Street joggers + sweater + leather sneakers

If you’re reluctant to leave the comfiness of athleisure, there’s no reason to anymore. The secret to wearing these casual looks at work is choosing real-clothes hybrids with sporty details. Try a jogger hybrid like the Madewell Twill Drawstring Jogger Pants ($80, madewell.com), add a sweatshirt-inspired pullover like the Gap Cozy Half-Zip Sweater in Stone Beige ($80, gap.com) and slip on leather sneakers like the Naturalizer Marianne Slip-On Sneaker–Women’s in Tan Embossed Leather ($85, dsw.com/en/us). Added up, they create a pulled-together effect that’s perfect for dress-down workplaces.
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PHOTO BY: Zappos; J.Jill; Macy's

(Left to right) Fireside by Dearfoams Sydney Genuine Shearling Scuff in Chestnut; J.Jill Lakewood Merino Sweater Tunic in Spiced Wine; NYDJ Plus Size Sculpt-Her Pull-On Ponte Flare Leg Pant in Black

4. Ponte pull-on pants + tunic sweater + shearling mules

For those of us working at home, it’s time to elevate our formula to a head-to-toe look. Though any colleague or client in Zoom meetings or on FaceTime sees you waist up, a total “outfit” gives you a psychological boost. Try a pair of pull-on ponte knit pants like the NYDJ Plus Size Sculpt-Her Pull-On Ponte Flare Leg Pant in Black ($89, macys.com). These are every bit as comfy as leggings but not as revealing or clingy. Add a long fine-gauge sweater like the J.Jill Lakewood Merino Sweater Tunic in Spiced Wine ($89, jjill.com) and toasty shearling-lined clogs or mules like the Fireside by Dearfoams Sydney Genuine Shearling Scuff in Chestnut ($50, zappos.com), and don’t forget some makeup! It’s perfect for WFH days but dressed enough to grab your coat and go with a change of shoes.
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PHOTO BY: Naadam; Catherines; Target

(Left to right) Naadam The Essential $75 Cashmere Sweater Women’s in Black; Comfortview Poloma Wide Calf Boot in Mocha; Who What Wear Faux Leather Skirt in Brown

5. A leather skirt + knee boots + a cashmere sweater

While plenty of us spend workdays in pants or jeans, some like the option of a skirt look, especially in urban or creative workplaces. No need to think about pencil skirts, shape wear and pumps. A leather skirt like the Who What Wear Faux Leather Skirt in Brown ($35, target.com) adds a chic tweak to all your tops. Try it with a kitten heel boot like the Comfortview Poloma Wide Calf Boot in Mocha or Multi Snake ($108–$130, catherines.com) and a classy sweater like Naadam’s The Essential $75 Cashmere Sweater Women’s in Black ($75, naadam.com), but know it’s a multi-season 24/7 piece that will look equally great with your shearling boots and a down vest.
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PHOTO BY: Anthropologie; Target; Macy's

(Left to right) Pilcro The Skipper Wide-Leg Jeans in Plus Size Black; Who What Wear Women’s Plus Long Sleeve Top in Jet Black Floral; Anne Klein Faux Leather Blazer in Anne Black

6. Black jeans + floral blouse + leather jacket

Some of us like a little downtown edge even in work clothes. The trick to making a cool look work for work is to start with inky black jeans as a stand-in for dress pants (just avoid faded and ripped black washes). Choose a straight- or wide-leg style like Pilcro The Skipper Wide-Leg Jeans in Plus Size Black ($130, anthropologie.com) as your base. Then add a puff sleeve blouse like the Who What Wear Women’s Plus Long Sleeve Top in Jet Black Floral ($30, target.com) for a feminine twist and top it all off with a leather blazer like the Anne Klein Faux Leather Blazer in Anne Black ($139, macys.com) for a business-like tweak on biker style.
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PHOTO BY: J.Jill; Bloomingdale's; Ann Taylor

(Left to right) J.Jill Wherever Smooth-Fit Slim-Leg Pants in Navy Blue; Aqua x Scout The City Balloon Sleeve Button-Front Shirt in White; Ann Taylor Pearlized Huggie Earrings

7. Tailored ankle pants + crisp white shirt + new-look pearls

Sure, you have a bunch of ankle pants from workdays past but are they high-rise with a stretchy waist and as comfy as sweatpants? Nope? And those white shirts, are they preppy button-downs? Thought so! New versions like the J.Jill Wherever Smooth-Fit Slim-Leg Pants in Navy Blue or Black ($79, jjill.com) with elastic waist sit at your real waist to make belly bulges and muffin tops a nonissue. Add a white shirt like Aqua x Scout The City Balloon Sleeve Button-Front Shirt in White ($78, bloomingdales.com) and Ann Taylor Pearlized Huggie Earrings ($35, anntaylor.com) to get a professional trio that lasts 9 to 5 and long after.
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PHOTO BY: Macy's; Target; DSW

(Left to right) Calvin Klein Tie-Waist Midi Sweater Dress; A New Day Women’s Plus Cable-Knit Open Front Cardigan in Charcoal Gray; Impo Nelia Bootie in Black

8. A midi sweater dress + long cardigan + booties

For those of us who still wear dresses, sweater dresses are another major trend worth trying. Stay away from skimpy above-the-knee clingers and body-con dresses and stick with straight or fit-and-flare midis, like the Calvin Klein Tie-Waist Midi Sweater Dress ($90, macys.com), that flatter but don’t overdo the curves. Add booties like the Impo Nelia Bootie in Black ($70, dsw.com/en/us) and a long toned-to-match cardigan like A New Day Women’s Plus Cable-Knit Open Front Cardigan in Charcoal Gray ($35, target.com) for extra warmth or coverage. Think of this as your new twinset.
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PHOTO BY: DSW; Walmart; Alex Mill; LOFT

Kate Spade Paris Ballet Flat (top left); C. Wonder Luna Quilted Satchel in Black (bottom left); Alex Mill Ribbed Sweater Tunic in Heather Latte (middle); Loft Pull On Wide Leg Pants in Birdseye Knit in Charcoal (right)

9. Wide-leg knit pants + tunic + quilted leather accessories

Knit duos are a big trend, but skip the clingy skirt twosomes and head straight for wide pants and tunics with enough shape, substance and coverage, like the Loft Pull On Wide Leg Pants in Birdseye Knit in Charcoal ($80, loft.com) and the Alex Mill Ribbed Sweater Tunic in Heather Latte or Navy ($138, alexmill.com). Both are comfy but have enough shape and substance to not look like loungewear. Be sure to stick with rich neutral colors and select a sweater long enough to cover your backside. Just add flats and a quilted leather bag like the Kate Spade Paris Ballet Flat ($90, dsw.com/en/us) and C. Wonder Luna Quilted Satchel in Black ($40, walmart.com) to take the look up yet another elegant notch.
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PHOTO BY: Macy's; M.M. LaFleur; 6pm

(Left to right) Le Suit Plus Size Pinstriped Pantsuit in Indigo/Ivory; M.M. LaFleur The Rowling Top-Soft Wave in Alabaster; Faryl by Farylrobin Solara in Cognac

10. Your pantsuit + cowl top or bodysuit + chunky pumps

Some of us work in corporate or traditional fields where pantsuits like Le Suit Plus Size Pinstriped Pantsuit in Indigo/Ivory ($119, macys.com) are business as usual. Keep the structure and tailoring going but freshen the look with a white drapey cowl neck bodysuit or top like the M.M. LaFleur The Rowling Top-Soft Wave in Alabaster ($145, mmlafleur.com) to wear untucked or tucked. Then swap needle heel pumps for chunky block heels like Faryl by Farylrobin Solara in Cognac ($45, 6pm.com) that can stand all day without an ouch, or swap to flats.

Lois Joy Johnson is a beauty and style editor who focuses on women 50 and older. She was the beauty and style editor at Ladies’ Home Journal and a founding editor of More magazine. She has written three books: The Makeup Wakeup, The Wardrobe Wakeup and The Woman's Wakeup.

10 New Ways to Dress for Work Now

Fashion finds to wear to every kind of workplace, from traditional to dress-casual

1. Black boot-cut + turtleneck + ankle boots

2. An oversize blazer + dark high-rise jeans + chunky loafers

3. Street joggers + sweater + leather sneakers

4. Ponte pull-on pants + tunic sweater + shearling mules

5. A leather skirt + knee boots + a cashmere sweater

6. Black jeans + floral blouse + leather jacket

7. Tailored ankle pants + crisp white shirt + new-look pearls

8. A midi sweater dress + long cardigan + booties

9. Wide-leg knit pants + tunic + quilted leather accessories

10. Your pantsuit + cowl top or bodysuit + chunky pumps

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