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Celebrate Special Occasions in Outfits Suitable for Summer

Weddings, cocktail parties and more require fashion ideas geared for the season

Lois Joy Johnson,

Updated July 09, 2026

AARP

Updated July 09, 2026

Key takeaways

Choose flowy midi or maxi dresses with prints for dressy events.
Build cocktail looks around white pants, bold tops and earrings.
Elevate casual outfits with colorful skirts, pants or mixed-media dresses.

Summer is a magical season. Longer daylight hours, tropical weather and incredible sunsets make being cooped up indoors the last thing anyone wants to do. It’s the perfect time for socializing and invitations that range from casual to classy, comfy to chic.

It seems like every phone call or text I receive starts with “What should I wear to…?” That’s because my job, as a beauty and style pro for women over 50, extends to personal shopping gigs. Here are the six top get-dressed-up summer events and the best sartorial solutions for each.

a collage with a pair of gold tone sandals with braided straps and three models wearing midi length dresses in floral patterns

(From left) LC Lauren Conrad Women’s Ruffle Wrap Maxi Dress in Blue Elina Fleurs; Petal and Pup Women’s Brigitte One-Shoulder Tiered Midi Dress in Black Floral; Gap Women Voile Smocked-Waist Maxi Dress in Tonal Blue Floral; Arezzo Women’s Paola Flat Sandal in Gold.

AARP (Kohl’s; Gap; Macy’s, 3)

1. A summer wedding or dressy party

Who doesn’t love the romantic vibe of an outdoor summer wedding, or a major birthday/anniversary celebration under blue skies? The invitation always brings a smile, followed immediately by: “What should I wear to that?” Browse the wedding guest dress category of your favorite site or retailer this year, and you’ll see slinky slip dresses and strapless corset styles, options which frankly don’t work for most mature women’s bodies. There are two things women over 50 insist on when looking for a glam summer dress. They say, “It has to work with a real bra,” and “No pantyhose or shapewear. I can’t do that in this heat.” What to look for? A flow-y, below the calf midi or an ankle-length maxi in an allover floral print, like the LC Lauren Conrad Women’s Ruffle Wrap Maxi Dress in Blue Elina Fleurs or Lake Sammy Stripe ($49, kohls.com); the Gap Women Voile Smocked-Waist Maxi Dress in Tonal Blue Floral ($100, gap.com); or the Petal and Pup Women’s Brigitte One-Shoulder Tiered Midi Dress in Black Floral ($89, macys.com). Here’s why this works: You not only get a bra-friendly dress and leg coverage, but the print visually disguises sweat stains and bulges. Sure, it’s an optical illusion, but one that always works! Note: One-shoulder dresses are a variation to consider, even for an afternoon wedding. A convertible bra or a strapless style is all you need in that case to keep your silhouette lifted (always check the side view, too). Opt for airy sandals, not closed pumps, which can look frumpy and trap sweat at the soles and toes. Check the venue and choose bare sandals with kitten heels, like the Marc Fisher LTD Women’s Alonde Slide Sandal in Light Natural or Mna 01 ($130, nordstrom.com) or the Christian Siriano New York Ixla Sandal in Taupe, White or Black ($79, dsw.com); or a flat style, like the Arezzo Women’s Paola Flat Sandal in Gold ($60, macys.com), if the day involves walking on grass or pebbly walkways.

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a collage with two pairs of statement earrings and two models wearing blouses with bold colors and patterns

(From left) Banana Republic Factory Paillette Earrings in Gold; Madewell Shell Statement Hoop Earrings in Antique Gold; Nic+Zoe Kauai Garden Crinkle Shirt in Red Multi; Ann Taylor Floral Tie-Waist Tee in Bright Cherry B.

AARP (Banana Republic Factory, Madewell, Bloomingdale’s, Ann Taylor)

2. A glam cocktail party

Think sunset cruises, rooftop drinks and patio soirees. A summer cocktails situation usually means face-to-face mingling and lots of standing or perching at high-top tables. All you need to do is emphasize the top of what you wear and add statement jewelry. One easy solution is to wear your favorite white pants or white jeans as a base (anything from slim to wide-leg goes here) and add an eye-catching top in a vibrant color or print, like the Liverpool Los Angeles Women’s Eyelet-Embroidered 3/4-Sleeve Top in Cherry Rose ($53, macys.com); the Ann Taylor Floral Tie-Waist Tee in Bright Cherry B ($38, anntaylor.com); or the Nic+Zoe Kauai Garden Crinkle Shirt in Red Multi ($109, bloomingdales.com) — and festive statement earrings. Dangles, drops and hoops, like the Madewell Shell Statement Hoop Earrings in Antique Gold ($45, madewell.com); Banana Republic Factory Women Paillette Earrings in Gold ($23, bananarepublicfactory.gapfactory.com); and By Anthropologie Paillette Cluster Drop Earrings in Peach, Coral, Turquoise, Chartreuse, Abalone or Pearl ($58, anthropologie.com), are conversation starters and guarantee a “Love your earrings!” compliment.

Most Popular

a collage with three models wearing stylish midi dresses

(From left) Quince Women Stretch Cotton Jersey Side-Tie Midi Dress in Chile; Croft & Barrow Women’s Smocked-Waist Midi in Gerbera Bloom; Gap Factory Women Smocked Boatneck Maxi Dress in Navy Floral.

AARP (Quince, Kohl’s, Gap Factory)

3. High school or college reunion

Never mind Facebook — this is your big chance to reconnect with old friends and classmates in person. No one cares if what you wear is old or new (they won’t know the difference anyway), or whether you’re a size 6 or 16. They’ll just be glad to see you. However, they will be checking you out. Women say they want “a no-fuss style that lets me relax about the fit and my body issues.” Once again, a dress is a surefire solution, since there’s no what-to-wear-with-what dilemma. Forgiving knit styles and dresses with smocking accommodate curves and glide over them. My advice? Resist dark neutral colors in this situation. You’ll get a cosmetic boost from a red, pink, coral or soft blue that not only brightens your look but makes you stand out in a crowd. Check out the Gap Factory Women Smocked Boatneck Maxi Dress in Modern Red, Navy Floral or Brown ($54, gapfactory.com); the White House Black Market Smocked-Waist Poplin Midi Dress in Orchid Flower ($120, whitehouseblackmarket.com); the Croft & Barrow Women’s Smocked-Waist Midi in Gerbera Bloom ($24, kohls.com); and the Quince Women Stretch Cotton Jersey Side-Tie Midi Dress in Chile or Moonstone Blue ($50, quince.com), all good choices.

a collage with two models wearing wide leg cropped pants in bold patterns, and one model wearing a midi skirt in light blue eyelet

(From left) On 34th Women’s Cotton Solid Eyelet Midi Skirt in Blue Cosmos; Cable & Gauge Women’s Printed Linen Blend Pull-On Crop Pants in Durango; Nine West Women’s Palazzo Pants in Navy Border Floral.

AARP (Macy’s, 2; Kohl’s)

4. Backyard bashes and barbecues

The get-together may be casual, but don’t fall back on your everyday runaround outfit. Sure, cookouts with friends, family and/or neighbors are still “dress-down” situations, but an elevated version of your usual look makes a real difference. The easiest solution is to pair a basic tee or tank (you can’t miss with white) with a more festive midi skirt or pull-on pants, depending on your preference. Keeping the style you love while amping up the color or opting for a print instead of a solid is the key here, giving your usual look an upgrade. Check out lively A-line skirts, like the On 34th Women’s Cotton Solid Eyelet Midi Skirt in Blue Cosmos ($66, macys.com); the Farmer’s Market Women’s Smocked-Waist Skirt ($44, kohls.com); and the J.Crew Factory Women’s Poplin Pull-On Midi Skirt in Vibrant Flame ($59, factory.jcrew.com), or comfy, wide-leg pants, like the Nine West Women’s Palazzo Pants in Navy Border Floral ($45, kohls.com); Caslon Women’s Wide-Leg Gauze Pants in Red Geranium ($47, nordstrom.com); Cable & Gauge Women’s Printed Linen Blend Pull-On Crop Pants in Durango ($41, macys.com); or Karen Kane Drawstring Cropped Pants in Paisley ($89, bloomingdales.com), for a more pulled-together effect.

a collage with a coral red short sleeve midi dress, and two models wearing midi dresses in darker colors

(From left) Boden Women Boat Neck Mix Dress in Blood Orange; Aqua Women Mixed-Media Maxi Dress in Navy/White; Simply Vera Vera Wang Mixed-Media Midi Dress in Beige Leopard Spots.

AARP (Boden, Bloomingdale’s, Kohl’s)

5. Alfresco dinner party or outdoor restaurant celebration

The likely setup here is group seating at a long or round table. Aim for what I call “tabletop dressing.” A mixed-media dress, which combines a stretchy, shapely tee or tank on top and a full midi or maxi skirt below the waist, is one of the most useful and flattering solutions. It’s also a major summer trend. Sometimes the fabric and color are the same on top and bottom (usually a jersey knit), and sometimes it’s a combo of a stretchy top and a structured skirt in a fabric like poplin. It all adds up to a dress that’s comfy on a steamy evening yet roomy enough to comfortably cross and uncross your legs. Mixed-media styles vary, as does the degree of skirt volume, from a flirty knit, like the Boden Women Boat Neck Mix Dress in Blood Orange ($110, us.boden.com), to a more refined and voluminous fit-and-flare, like the Simply Vera Vera Wang Mixed-Media Midi Dress in Beige Leopard Spots, Navy Dye Bouquet or Pink Water Blooms ($42, kohls.com); the Aqua Women Mixed-Media Maxi Dress in Navy/White ($78, bloomingdales.com); and the elegant Anne Klein Women Sleeveless Mixed-Media Midi Dress in Anne Black ($169, nordstrom.com), with a removable belt, for those who love a classic little black dress.

6. An outdoor concert, play or performance

This is a what, when and where moment. Whether you’re going to a rock concert or a jazz festival where everyone is in jeans, or an evening of outdoor theater or a symphony in the park with folding lawn chairs, gourmet picnic baskets and wine, make a style effort. The best way to quickly dress up jeans and clogs or your most down-to-earth footbed sandals is by trading the tee for a lightweight, boho-inspired top, like the Coldwater Creek Summer Breeze Twist of Gauze Top in Crema ($90, coldwatercreek.com); the Universal Thread Women’s Long-Sleeve Gauze Button-Front Blouse in Cream ($24, target.com); or the Gap Women Lace-Trim Pintuck Top in New Off White ($80, gap.com), personalized with your favorite layered necklaces, stack of bangles or dangle earrings. Why white? It adds radiance to your skin and gives even your oldest, faded or frayed-hem jeans a sophisticated look. For more refined evening events (or for anyone not into jeans or boho), simplify. Long, loose, A-line dresses, another dress 2026 trend, are wildly body-friendly and forgiving of extra pounds, and they also keep you cool. Check out the Nine West Women’s Tiered Maxi Dress in Green Botanic Zebra or Shady Moss ($42, kohls.com), a tiered pull-on with a raised waist for those who prefer some subtle definition; and the Talbots Jersey V-Neck Maxi Dress - Abstract Floral in Black/Ivory ($149, talbots.com); or the T Tahari Women’s Sleeveless Double V-Neck A-Line Maxi Dress in Palm Cascade ($178, macys.com). These are two looks with lots of low-key glamour.

The key takeaways were created with the assistance of generative AI. An AARP editor reviewed and refined the content for accuracy and clarity.

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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