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9 New Ways to Dress for Special Events

Stylish solutions for cocktail parties, reunions, weddings and more


spinner image Four women sitting outside drinking wine while talking to each other
SolStock/E+/Getty Images

 

Dressing up is not the way it used to be. We pair tailored blazers with sporty leggings, fancy blouses with vintage jeans and romantic dresses with edgy leather jackets. Shirts that expose shoulders have replaced cleavage-baring tops; midis substitute for minis; and sandals have pushed nude pantyhose and pumps to the curb. We have a que será, será approach to closet clean-outs, donating and tossing without a tear. But then we review our wardrobe and panic: What do we wear for the next big RSVP or summer e-vite? Relax. “Appropriate attire” at 50 is easier than ever.

spinner image RACHEL Rachel Roy Bret Jersey Dress in Leopard; Liz Claiborne Short Sleeve Wrap-Dress in Signature Blue; Lane Bryant Surplice-Neck Side-Ruched Midi Dress in Anthem Stripe; A New Day Women’s Celeste Mules in Tan
(Left to right) RACHEL Rachel Roy Bret Jersey Dress in Leopard; Liz Claiborne Short Sleeve Wrap-Dress in Signature Blue; Lane Bryant Surplice-Neck Side-Ruched Midi Dress in Anthem Stripe; A New Day Women’s Celeste Mules in Tan
Macy's; JCPenney; Lane Bryant; Target

1. High school or college reunion

This is your big chance to reconnect with old classmates face to face. Trust me, no one cares if your dress is from Saks or Target; if you’re wearing a designer label or a discount mall bargain; and most of all if you’re a size 16 and not your old size 8. Focus on a favorite “feel-good” outfit in a color or fun print that’ll stand out in the crowd. When someone says, “Where’s Stella?” the answer is “She’s the one in leopard” or “Look for a striped dress.” A comfy pull-on style like the RACHEL Rachel Roy Bret Jersey Dress in Leopard ($83, macys.com) and wrap styles like the Liz Claiborne Short Sleeve Wrap-Dress in Signature Blue ($52, jcpenney.com) or Lane Bryant Surplice-Neck Side-Ruched Midi Dress in Anthem Stripe ($48, lanebryant.com) dress up or down with a surge of star power. Just add fancy flats like the A New Day Women’s Celeste Mules in Tan, Off-White or Black ($30, target.com) and a small bag to keep cell, lipstick and breath mints handy.

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spinner image LuvMeMore Heatwave Off the Shoulder Duster in Black/Forest Green; Studio 1 Plus Short-Sleeve Off-the-Shoulder Floral Midi Fit & Flare Dress in Navy Ivory; Anne Klein Straight Cropped-Leg Ankle Pants; Calvin Klein Fire 2 Slide Sandal in Pink
LuvMeMore Heatwave Off the Shoulder Duster in Black/Forest Green (left); Studio 1 Plus Short-Sleeve Off-the-Shoulder Floral Midi Fit & Flare Dress in Navy Ivory (middle); Anne Klein Straight Cropped-Leg Ankle Pants (top right); Calvin Klein Fire 2 Slide Sandal in Pink (bottom right)
Dia & Co; JCPenney; Macy's; DSW

2. A cocktail party, rehearsal dinner or alfresco lunch for six

These middle-of-the-road festivities are a chance to highlight your style or try something new. Depending on venue, situation and your mood try a floaty bare-shoulder midi like the Studio 1 Plus Short-Sleeve Off-the-Shoulder Floral Midi Fit & Flare Dress in Navy Ivory ($60, jcpenney.com). You can also pair a statement top like the Banana Republic Balloon-Sleeve Wrap Top in Yellow Umbrella ($130, bananarepublic.gap.com, not pictured) or a dazzling duster like the LuvMeMore Heatwave Off the Shoulder Duster in Black/Forest Green ($40, shop.dia.com) with white ankle pants like the Anne Klein Straight Cropped-Leg Ankle Pants ($62, macys.com). This is the time for your boldest costume jewelry and a pair of trendy slides or mules like the Calvin Klein Fire 2 Slide Sandal in Pink or Green ($90, dsw.com/en/us) and a pedicure.

spinner image Loft Curvy Riviera Slim Pants in Forever Navy; Mango Linen Blazer Suit in Red; Livid Casey Scuba Flare Dress in Navy; H&M Single-Breasted Women’s Jacket in Taupe
(Clockwise from left) Loft Curvy Riviera Slim Pants in Forever Navy; Mango Linen Blazer Suit in Red; Livid Casey Scuba Flare Dress in Navy; H&M Single-Breasted Women’s Jacket in Taupe
LOFT; Mango; Dia & Co; H&M

3. A job interview

Even if your interview is a virtual one, pull together a head-to-toe look for a more confident attitude. It’ll show on screen in your face and body language. You can’t lose in a neutral pant/blazer combo like the H&M Single-Breasted Women’s Jacket in Taupe ($35, www2.hm.com/en_us) and the Loft Curvy Riviera Slim Pants in Forever Navy or Black ($80, loft.com) to project instant power. Frame your face with a crisp white shirt or blouse under that blazer for extra radiance. For a second callback or when the job is in retail, fashion or public relations, choose a colorful blazer like the Mango Linen Blazer Suit in Red ($120, shop.mango.com/us) or a fit-and-flare dress like the Livid Casey Scuba Flare Dress in Navy or Black ($79, shop.dia.com) to look up to date, but keep the focus on your skills and abilities. For desk-side interviews, wear closed-toe shoes and carry a structured workbag.

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spinner image Ava & Viv Women’s Plus Size Balloon Lon Sleeve Dress in Green; River Island Black Shirred Smock Midi Dress; Kiyonna Plus Flirty Flounce Wrap Dress in Navy Floral Print; Journee Collection Angelina Wedge Sandal in Nude
(Left to right) Ava & Viv Women’s Plus Size Balloon Lon Sleeve Dress in Green; River Island Black Shirred Smock Midi Dress; Kiyonna Plus Flirty Flounce Wrap Dress in Navy Floral Print; Journee Collection Angelina Wedge Sandal in Nude
Target; River Island; Nordstrom; DSW

4. A summer wedding or elegant outdoorsy party

As fancy as it gets, but the big issues here are sweat, sunburn and humidity so forget about wearing anything tight and constricting (including major shape wear). A graceful midi dress with voluminous sleeves, like the Ava & Viv Women’s Plus Size Balloon Lon Sleeve Dress in Green ($35, target.com), River Island Black Shirred Smock Midi Dress ($74, riverisland.com/us/women) or Kiyonna Plus Flirty Flounce Wrap Dress in Navy Floral Print ($98, nordstrom.com), will let air circulate, camouflage a few extra pounds and make sitting crossed-leg perspiration proof. Add wedge sandals like the Journee Collection Angelina Wedge Sandal in Nude or Pink ($55, dsw.com/en/us) for grassy strolls, and carry sun protection for a touch-up in your clutch.

spinner image Ava & Viv Women’s Plus Size Long Sleeve Ruched Bodice Dress in Black; Who What Wear Women’s Plus Elbow-Sleeve Polo Rib Dress in Black; Sam Edelman Women’s Connell Slingback Flats in Black
(Left to right) Ava & Viv Women’s Plus Size Long Sleeve Ruched Bodice Dress in Black; Who What Wear Women’s Plus Elbow-Sleeve Polo Rib Dress in Black; Sam Edelman Women’s Connell Slingback Flats in Black
Target (2); Bloomingdale's

5. For a funeral, wake, memorial or celebration of life

This is not the moment for your favorite zebra print blouse or a pastel dress no matter how demure. Say no to sneakers, statement earrings and stacks of clanky bangles, too. Quiet and low-key is the idea. A black pants or skirt outfit (dark gray or navy if you don’t have black) or a black dress like the Ava & Viv Women’s Plus Size Long Sleeve Ruched Bodice Dress in Black ($25, target.com) or Who What Wear Women’s Plus Elbow-Sleeve Polo Rib Dress in Black ($37, target.com) sets the right tone. You may want to add grass-proof closed-toe shoes like the Sam Edelman Women’s Connell Slingback Flats in Black ($120, bloomingdales.com) for funeral attendance. One caveat: If the celebration of life asks specifically for attendees to wear white or joyful colors (and some do these days) do participate.

spinner image NYDJ Marilyn Straight-Leg Jeans in Optic White; Caslon Stripe Split-Neck Long-Sleeve T-Shirt in Blue-White Charm Stripe; River Island Orange Print Shirt; Stella Carakasi Tiburon Tunic Icon in Kiwi
(Left to right) NYDJ Marilyn Straight-Leg Jeans in Optic White; Caslon Stripe Split-Neck Long-Sleeve T-Shirt in Blue-White Charm Stripe; River Island Orange Print Shirt; Stella Carakasi Tiburon Tunic Icon in Kiwi
Bloomingdale's; Nordstrom; River Island; Stella Carakasi

6. For a first date

It’s an insta-date world so no more, “He’ll have to call me by Tuesday to see me on Saturday.” A casual coffee or glass of wine is all it takes these days to say yea or nay to an online match or a fix-up by friends. White jeans like NYDJ Marilyn Straight-Leg Jeans in Optic White ($119, bloomingdales.com) always look fresh in summer but it’s the top that reveals your personality so give that more thought. A polished T-shirt like the Caslon Stripe Split-Neck Long-Sleeve T-Shirt in Blue-White Charm Stripe or Red-White Charm Stripe ($39, nordstrom.com), an eye-catching blouse like the River Island Orange Print Shirt ($67, riverisland.com) or a classic tunic in a flattering-for-you color, like the Stella Carakasi Tiburon Tunic Icon in Kiwi ($169, stellacarakasi.com), will make you feel current. Just tousle your hair, brush your teeth, add some blush or lipstick and a spritz of perfume.

spinner image Foxcroft Vena Cotton Gauze Tunic in White; Chico’s Cotton-Blend Slub Drama-Sleeve Top in Alabaster; Wit & Wisdom Eyelet Popover Top in Optic White; Madewell Pull-On Midi Skirt in Shibori Indigo Plaid; Esprit Women’s Narissa Ballet Flats in Black
(Clockwise from left) Foxcroft Vena Cotton Gauze Tunic in White; Chico’s Cotton-Blend Slub Drama-Sleeve Top in Alabaster; Wit & Wisdom Eyelet Popover Top in Optic White; Madewell Pull-On Midi Skirt in Shibori Indigo Plaid; Esprit Women’s Narissa Ballet Flats in Black
Nordstrom; Chico's; Nordstrom; Madewell; Macy's

7. A concert

Well … it depends on what, when and where, doesn’t it? A rock concert or bluegrass evening in the park might mean jeans, but an orchestrated evening of Brahms, opera at the theater or a string quartet at your local community center deserves more polish. There’s an easy solution for all. A fashionable white top — a blouse like the Wit & Wisdom Eyelet Popover Top in Optic White ($79, nordstrom.com), a derriere-covering tunic like the Foxcroft Vena Cotton Gauze Tunic in White ($79, nordstrom.com) or a trendy-sleeved tee like the Chico’s Cotton-Blend Slub Drama-Sleeve Top in Alabaster ($29, chicos.com) — works with a variety of bottom options from jeans to pants to breezy midi skirts like the Madewell Pull-On Midi Skirt in Shibori Indigo Plaid ($95, madewell.com). Slip on black ballet flats like the Esprit Women’s Narissa Ballet Flats in Black ($34, macys.com) for an elegant finish either way.

spinner image Lands’ End Women’s Plus-Size Cotton Jersey Embroidered Sleeveless Swim Cover-Up Dress in Papaya Orange/White; L.L. Bean Women’s SunSmart UPF50+ Cover-Up Dress in Black and White Palms; Lou & Grey Signaturesoft Tank Midi Pocket Dress in Balsam Green
(Left to right) Lands’ End Women’s Plus-Size Cotton Jersey Embroidered Sleeveless Swim Cover-Up Dress in Papaya Orange/White; L.L. Bean Women’s SunSmart UPF50+ Cover-Up Dress in Black and White Palms; Lou & Grey Signaturesoft Tank Midi Pocket Dress in Balsam Green
Lands' End; L.L. Bean; LOFT

8. A beach or pool party

This is the invitation that gives many women pause because it means a swimsuit. But does it really? Not necessarily! Wear a cover-up dress like the L.L. Bean Women’s SunSmart UPF50+ Cover-Up Dress in Black and White Palms ($70, llbean.com), Lands’ End Women’s Plus-Size Cotton Jersey Embroidered Sleeveless Swim Cover-Up Dress in Papaya Orange/White ($32, landsend.com) or Lou & Grey Signaturesoft Tank Midi Pocket Dress in Balsam Green or Black ($75, loft.com) over any black one-piece (just in case) and you’re done. You’ll look chic and feel under no obligation to show anything more unless you want to. 

spinner image Croft & Barrow Women’s Comfortable Pull-On Jean Shorts in Dark Wash; GapFit Breathe Sweatshirt in Heather Grey; Columbia Women’s Anytime Outdoor Bermuda Shorts in Black; Sonoma Goods for Life Women’s Comfort Waist Utility Capri Pants in Khaki; Kelly & Katie Ellina Mesh Slip-On Sneaker in Off-White
(Clockwise from top left) Croft & Barrow Women’s Comfortable Pull-On Jean Shorts in Dark Wash; GapFit Breathe Sweatshirt in Heather Grey; Columbia Women’s Anytime Outdoor Bermuda Shorts in Black; Sonoma Goods for Life Women’s Comfort Waist Utility Capri Pants in Khaki; Kelly & Katie Ellina Mesh Slip-On Sneaker in Off-White
Kohl's; Gap; Kohl's (2); DSW

9. A sports event

Outdoorsy days are often a mash-up of outfits that are either lacking in style or uncomfortable for hours of sitting in the bleachers, on the sidelines or on a boat. Whether you’re invited to a baseball game, a sailing party or a golf match, do yourself a favor and pull together a real look. Start with lightweight slip-on sneakers like the Kelly & Katie Ellina Mesh Slip-On Sneaker in Off-White or Grey ($50, dsw.com/en/us) and then add capris like the Sonoma Goods for Life Women’s Comfort Waist Utility Capri Pants in Khaki or Chic Mauve ($24, kohls.com) for full coverage, or pull-on denim Bermuda-length shorts like the Croft & Barrow Women’s Comfortable Pull-On Jean Shorts in Dark Wash or Medium Wash ($25, kohls.com) or the Columbia Women’s Anytime Outdoor Bermuda Shorts in Black, Nocturnal or Tusk ($45, kohls.com) for bare-leg freedom. Add a tee and a light sweatshirt like the GapFit Breathe Sweatshirt in Heather Grey or True Black ($19, gap.com) for chill prevention.

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.

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