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Must-Have Spring Dresses for Every Occasion

Figure-flattering styles and chic designs for workdays, weddings and everything in between


a collage with models wearing fashionable spring dresses
(From left) You can find a dress to suit any occasion. Opt for flattering styles like the Lane Bryant Short-Sleeve Maxi T-Shirt Dress in Berry Pink; Loft Poplin Smocked Pocket Midi Dress in Java Chip; Lane Bryant Short Flutter-Sleeve Maxi Dress in Green Orchid; and Ann Taylor Eyelet Halter Maxi Dress in Smoldering Red.
AARP (Lane Bryant, 2; Loft; Ann Taylor)

Dresses are a welcome change from pants, leggings, layers and mixing and matching. You throw one on and presto: instant outfit! This spring, there’s even more incentive for women over 50 to buy dresses. You’ll see waist-defining dresses (that don’t require an actual waist), sophisticated colors like red, brown and burgundy (that feel new), floral prints (that disguise extra pounds), a variety of flattering sleeves and necklines (that slim upper arms and lengthen the neck) and midi/maxi lengths (that make going bare-legged a snap). I’m a fashion editor and personal shopper for women over 50 who sees all the buys, the keepers and the returns. Here are the 6 best spring dresses to consider now for every style:

a collage with models wearing comfortable loose fitting dresses for spring
(From left) Everlane Women Weekend Tee Midi Dress in Black; Lane Bryant Short-Sleeve Maxi T-Shirt Dress in Berry Pink; Old Navy Women Vintage Crew-Neck Maxi Dress in Crayon Blue; Cupshe Women’s Denim Short Sleeve Button-Down Cover Up Dress in Light Pastel Blue.
AARP (Everlane, Lane Bryant, Old Navy, Macy’s)

1. The casual, ‘I-love-sneakers’ dress

If sneakers, jeans and a tee are your idea of bliss, and being comfy is your top priority, take a look at the expanded category of “run-around” dresses. Roomy, relaxed and laid-back, they slip on like your favorite everyday tees, polos and chambray shirts, only this time in elongated midi and maxi dress lengths.

The most casual are loose, no-frills, T-shirt dresses, like the Old Navy Women Vintage Crew-Neck Maxi Dress in Crayon Blue, Dragonfruit or Black Jack ($15, oldnavy.gap.com); the Lane Bryant Short-Sleeve Maxi T-Shirt Dress in Berry Pink or Black ($35, lanebryant.com); and the Everlane Women Weekend Tee Midi Dress in Black, Beech or Charcoal Gray ($78, everlane.com), to pair with kicks and a jean jacket now, and to wear solo as the weather warms up.

For a little more structure and shape, try a straight, button-front “chambray/denim” shift, like the Cupshe Women’s Denim Short Sleeve Button-Down Cover Up Dress in Light Pastel Blue or Dark Blue ($66, macys.com) or the Soft Surroundings Je Veux Midi Shirtdress in Denim Blue ($120, softsurroundings.com), or a breezy shift like the DKNY Women Sleeveless Chambray Midi Dress in Stream ($129, nordstrom.com). All are perfect for running errands, a day at the farmer’s market, a street fair, a brunch or lunch out, a backyard barbecue with family, or just hanging out at home. You can let them double as beach/pool cover-ups later in the season, too.

Super tip: Pay attention to dress length, and grab your tape measure. While photos and model-height details can help, retailers have started listing the exact length of midi and maxi dresses in their online descriptions, and, in some cases, offering petite and regular lengths. This is important since you don’t want to get stuck with a midi that hits at the wrong spot, like the widest part of your calf, or a maxi that trails on the ground. Of course, a tweak at the tailor always helps, but that’s an additional cost to consider.

a collage with models wearing spring dresses in shades of bright red
(From left) A New Day Women’s Short Sleeve Pleated Midi Shirtdress in Geranium Red; Eloquii Women’s Tie-Front Oversized Shirt Dress in Barbados Cherry; Boden Women’s Mathilde Tie-Waist Ponte Dress in Spicy Red; Ann Taylor Eyelet Halter Maxi Dress in Smoldering Red.
AARP (Target, Macy’s, Boden, Ann Taylor)

2. The ‘brighten-my-look’ dress

Color turns any dress into a fashion statement, but a red dress is the no-fail answer to “I have nothing to wear.” In fact, this spring, a red dress is the new little black dress. It looks sharp for the day with black accessories and festive at night with metallic gold. Like red lipstick, a vibrant-hued dress warms fatigued skin and wakes up your look. However, not any old red dress is a winner, so be picky.

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My advice? Look for figure-friendly styles, like the Eloquii Women’s Tie Front Oversized Shirt Dress in Barbados Cherry ($80, macys.com) with a wide adjustable waist sash; the Ann Taylor Eyelet Halter Maxi Dress in Smoldering Red ($229, anntaylor.com), a halter-style maxi dress; A New Day Women’s Short Sleeve Pleated Midi Shirtdress in Geranium Red ($40, target.com), a fit-and-flare style; and the Boden Women’s Mathilde Tie Waist Ponte Dress in Navy or Spicy Red ($180, boden.com), a shape-maker with a boat neck and elbow-length sleeves. Where to wear red? Parties, meetings, reunions or any time you want to stand out in a crowd or just want a feel-good lift. 

Super tip: No need for a professional “color consultant” to determine if that red dress is for you. Just check your foundation, blush and lipstick for cues. Cool cherry, berry and ruby reds flatter cool skin tones; fiery tomato and orangey reds flatter warmer complexions.

a collage with models wearing stylish spring dresses in muted colors
(From left) Madewell Women Smocked V-Neck Midi Dress in Classic Navy; Gap Factory Women V-Neck Tie-Front Maxi Dress in Black Polka Dot; Loft Poplin Smocked Pocket Midi Dress in Java Chip.
AARP (Madewell, Gap Factory, Loft)

3. The ‘shape-me-up-fast’ dress

Many women consider a dress to be fashion therapy. One of the biggest wishes I hear is “I want a great dress that makes my body look better.” A dress can be loaded with style and have the trendiest look going, but if it doesn’t flatter when you have a few extra pounds or flabby upper arms, forget it! This spring, a shape-shifting answer has arrived in one particular dress style that happens to be a fast fix for all of the above. It’s almost as if designers got together and said “Let’s give women the perfect body-boosting dress.” Well, they did, and it’s a winner.

The essentials are a V-neck, some sort of full sleeve (loose, blouson or fluttery), an elastic smocked waist or bodice, and a fit-and-flare shape. Take a look at the Madewell Women Smocked V-Neck Midi Dress in Classic Navy ($158, madewell.com), the Loft Poplin Smocked Pocket Midi Dress in Lakeside Night or Java Chip ($41, loft.com); and the Gap Factory Women V-Neck Tie-Front Maxi Dress in Black Polka Dot ($40, gapfactory.com). Wear it for a confidence boost anytime, but especially for high-stress moments like a job interview, a class reunion, your sexy younger sister’s 50th birthday party or a first post-divorce dinner date. You’ll feel empowered.

Super tip: Don’t be tricked by all the “corset-style” dresses around. They don’t have laces, but you’ll recognize the cinched-midriff look in belt-free shirtdresses that are defined by a fitted, pin-tucked section below the bust. They zero in on the waist and muffin-top area: exactly where you don’t want attention. The same goes for low-waist dresses that extend below the belly. Same issue. Just say no.

a collage with models wearing stylish spring dresses in floral prints
(From left) Lane Bryant Short Flutter-Sleeve Maxi Dress in Green Orchid; Simply Vera Vera Wang Women’s Short Sleeve Maxi Dress in Purple Pink Floral; J.Jill Flutter-Sleeve Midi Dress in Prussian Blue Jacobean Vines.
AARP (Lane Bryant, Kohl’s, J.Jill)

4. The ‘dress-to-impress’ floral dress

Count on this one for a “You look great!” or at least a “Love your dress!” compliment. The print vibe is a contagious mood-changer this spring. If you’re on the fence about florals, realize that all these romantic prints have a secret ability to blur away extra pounds and bulges and give uneven body proportions a more balanced look, like a more generous top and a slimmer bottom (or vice versa). It’s an optical illusion, but one that works.

Do yourself a style favor and try a floral dress with a shape-enhancing elasticized waist, like the J.Jill Flutter-Sleeve Midi Dress in Prussian Blue Jacobean Vines ($80, jjill.com); the Lane Bryant Short Flutter Sleeve Maxi Dress in Green Orchid or Pink Floral ($55, lanebryant.com); or the Simply Vera Vera Wang Women’s Short Sleeve Maxi Dress in Purple Pink Floral or Black White Floral ($70, kohls.com). Bet you can’t buy only one!

Super tip: The most appealing prints now are those in cheery, springlike colors. If you’ve never worn floral prints before or at least not recently, start with those in a familiar neutral color, or in brights and pastels that have a dark neutral or black background.

a collage with models wearing stylish shirt dresses with wrap belts
(From left) Lands’ End Womens Poplin Midi Wrap-Front Dress in Midnight Sky Pinstripe; Banana Republic Factory Women Chambray Utility Midi Dress in Landslide Green; Lane Bryant Lena Knit Wrap Midi Dress in Navy Dot; I.N.C. International Concepts Women’s Long-Sleeve Geo Print Shirtdress in Rilla Patch.
AARP (Lands’ End, Banana Republic Factory, Lane Bryant, Macy’s)

5. The ‘I-mean-business’ work dress

Except for the most serious workplaces, dresses have pretty much replaced blazers and pantsuits as the spring/summer “dress code.” Whether you’re going back to work, own your business, freelance a few days a week, fundraise, work from home with Zoom meetings or temp at an office, stick to dresses with a businesslike attitude. That means a hint of structure (even a collar can spruce up a knit dress), neutral or medium-to-dark muted colors, stripes or prints (and yes, you can even wear florals or denim).

First choice is any kind of shirtdress, like the Lands’ End Womens Poplin Midi Wrap Front Dress in Midnight Sky Pinstripe or Sapphire Gem Blue Broad Stripe ($135, landsend.com); the I.N.C. International Concepts Women’s Long Sleeve Geo Print Shirtdress in Rilla Patch ($135, macys.com); the Ann Taylor Floral Satin Midi Shirtdress in Sky Gazing ($189, anntaylor.com); or a so-called “utility dress,” such as the Banana Republic Factory Women Chambray Utility Midi Dress in Landslide Green or Mauve Wine ($70, bananarepublicfactory.gapfactory.com). The latter style is actually just a multi-pocketed shirtdress with a sporty, cargo-pant vibe.

Runners-up are curve-controlling wraps, like the Lauren Ralph Lauren Women Plus Size Belted Crepe Surplice Neck Maxi Dress in Lighthouse Navy ($165, macys.com) and the Lane Bryant Lena Knit Wrap Midi Dress in Navy Dot ($55, lanebryant.com); and collared knits, like the J.Crew Factory Women Striped Collared Knit Dress in Antique Navy Ivory ($65, factory.jcrew.com) and the Ann Taylor Pleated Polo Sweater Dress in Subdued Navy or Cafe Au Lait ($198, anntaylor.com) with a full-A-line skirt.

Super tip: To keep shirtdresses and utility-style dresses from looking stuffy, avoid buttoning them up to the neck and down to the very last button at the hem. Unbutton the neckline to a V (avoid going too low or revealing cleavage crack). This helps elongate your neck and upper body for a slim, sleek effect on screens or over a desk or tabletop. And for those who can handle a discreet flash of leg, unbutton the bottom couple of buttons to knee-length.

a collage with  models wearing dressy spring frocks in various colors
(From left) Kiyonna Women’s Plus Size Veronica Ruffled Evening Gown in Onyx; Old Navy Off-The-Shoulder Boho Maxi Dress in Red Ditsy; Petal and Pup Brigette One-Shoulder Tiered Midi Dress in Red Floral; Donna Karan New York Women’s V-Neck Midi Dress in Taffeta Blue.
AARP (Macy’s, Old Navy, Target, Macy’s)

6. The ‘I-want-to-look-glam’ wedding-guest dress 

It’s the start of wedding season, and the drama begins. What to wear is always a big deal. You want to look a little flirtatious or show off your shape, but you don’t want to deal with thigh-high slits or cleavage. You also want freedom of movement to sit, cross your legs, climb stairs and dance, and a dress that looks great with flat sandals or low kitten-heel slingbacks. And let’s be honest — you want a dress that will perform some helpful magic around your middle, too.

Wedding venues and attitudes vary in spring, from formal to beach and garden-party casual, but there’s a dress for every time you attend a wedding. Ruffles are “in” and are the first stop for proper camouflage (so you can leave the shapewear at home). Take a look at the faux-wrap Kiyonna Women’s Plus Size Veronica Ruffled Evening Gown in Onyx ($198, macys.com) with cascading front ruffles; the Petal and Pup Brigette One Shoulder Tiered Midi Dress in Red Floral ($99, target.com); and the Vince Camuto Flutter Sleeve Tiered Dress in Rich Black ($129, nordstrom.com), with layers of mini ruffles in tiers (the latter dress even has that trending elastic waist).

For a more minimalist style, try a one-shoulder dress, like the Mango Women Asymmetrical Dress with Side Slit in Burgundy or Tobacco Brown ($90, shop.mango.com), or an off-the-shoulder dress, like the Old Navy Women Off-The-Shoulder Boho Maxi Dress in Black Jack ($30, oldnavy.gap.com); the same dress in Blue Floral or Red Ditsy can also work for a more informal affair. Last but not least, there’s the Loft Smocked Off The Shoulder Maxi Dress in Chocolate Bark ($41, loft.com), with ruching in front for ease. 

Super tip: Color is a big question for dressy dresses. Black never goes out of style, and you can wear a black event dress all year round, multiple times, and no one will notice you’re wearing the same dress. It’s indestructible — you can even spill red wine on it without panicking! Don’t hesitate to try the new rich brown, deep berry and burgundy colors now — they offer similar slimming benefits and can soften the look of sun-damaged skin on the chest, arms, shoulders and legs.

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