Summer dresses are one of the easiest ways to get dressed this time of year, and I’ve been reaching for them more than ever lately. They’re cool, comfortable, and with the right shoes and accessories, they can take you just about anywhere.
Today I’m sharing some of my favorite dresses from this season, along with how I’d style each one for a different occasion. Whether you’re heading on vacation, meeting friends for brunch, or dressing for a special event, I hope these outfit ideas give you a little inspiration for making the most of your wardrobe during these dog days of summer.
Weekend Errands
Splendid Wren Mini Dress (M) // Quince Leather Flip-Flops // Madewell Mylie Raffia Bag // Jenny Bird Florence Earrings // Bryan Anthonys Sea Seeker Pendant & You Are My Sunshine Necklace // Cyndi’s Bracelet Stack // Tom Ford sunnies
I’ll be the first to admit, I usually reach for a pair of cropped jeans or shorts when I’m headed out to run errands in the summertime, but I’d like to challenge myself to choose a dress more often. This easy shift dress is made from a breezy lyocell-linen blend, so it’s cool and comfortable on a hot day while looking a lot more polished than my typical denim shorts.
Instead of sneakers, I chose leather flip-flops to give this outfit a relaxed, minimalist feel that’s very on trend right now. Then I added a roomy raffia shoulder bag and a few simple accessories to complete the look.
Wine Tasting
LOFT Scalloped Floral Eyelet Mini Dress (M) // Loeffler Randall Jovie Brown Jelly Flip Flop c/o (8) // Madewell Woven Zip Top Shoulder Bag // Jenny Bird Florence Earrings // Jane Win Grace Pendant Necklace // Cyndi’s Bracelet Stack
This scalloped eyelet dress is one of my favorite finds this season, and I think it would be perfect for an afternoon at a local winery. The clean shift silhouette balances the feminine floral eyelet and scalloped details.
To keep the dress the focal point, I kept the rest of the styling simple. The jelly thong sandals with gold hardware feel fresh and on trend while being comfortable enough for walking around, and the deep espresso woven bag is a modern touch that adds texture and picks up the rich brown tones in the embroidery.
Church or Lunch with Friends
Tommy Bahama Sunset Harbor Lace Trim Dress (M) // Dolce Vita Laurie Wedge Sandal (8) // Rebecca Minkoff Edie // Tom Ford sunnies
This polished cotton dress is the kind of piece that’s appropriate for so many daytime occasions, from church to lunch with friends. The lace trim gives it subtle texture, and the removable belt lets you change the look depending on your mood.
I paired it with neutral raffia wedge sandals to complement the texture of the dress and carried a shoulder bag in a similar color and texture to keep the look cohesive. A few simple pieces of gold jewelry add just the right finishing touch.
Casual Summer Party
Talbots Jersey V-Neck Dress c/o (S) // Loeffler Randall Jovie Brown Jelly Flip Flop c/o (8) // Bryan Anthony’s Mom Coin Necklace & Our Light Necklace
This printed jersey dress is the perfect choice for a casual summer party or family get-together. It has a flattering silhouette while still being relaxed and comfortable. The flounce hem adds a fun, feminine touch, while the brown medallion print on an ivory background gives it a subtle boho vibe that appeals to me.
I kept the styling simple, much like the white scalloped eyelet dress, with the same brown jelly flip-flops. The gold hardware elevates them just enough, and the cushioned footbed keeps them comfortable if you’re on your feet mingling all afternoon or evening.
Farmer’s Market
Splendid Maggie Poplin Dress (M) // Splendid Asher Studded Sandal in Caramel (8)
I’m assuming for most of us, a trip to the farmer’s market usually means a tank top and shorts. (At least it does for me!) But if I were going to dress up just a little, this is exactly what I’d wear.
I’m loving the classic cotton poplin midi dresses that are everywhere this season, and this navy one is surprisingly flattering. The structured bodice and carefully placed pleats create shape through the waist and hips before falling into an easy, full skirt. The silhouette feels timeless, with subtle details that keep it fresh and modern.
I paired it with simple T-strap sandals in a warm cognac leather for a classic, understated look. I’d add a few simple pieces of jewelry, maybe a fun hat, and of course a straw or canvas tote to complete the outfit.
Tropical Sightseeing
Mary Textured Shift Dress (M) // Dolce Vita Dom Strappy Sandals (8) // Eric Javits Hampton Straw Packable Hat // similar tote // Quince Globe Hoops
When I’m sightseeing on vacation, I want an outfit that’s comfortable and polished, and dresses are one of the easiest things to pack. This textured shift dress is lightweight, doesn’t wrinkle easily, and can even double as a swim cover-up to get more mileage out of it during your trip. (It’s also on sale right now, and fully stocked!)
I added a wide-brim straw hat for sun protection, carried a sleek straw tote, and finished the look with comfortable cognac leather sandals. I love the combination of the strappy upper and the molded footbed. They’re perfect for long days of sightseeing without sacrificing style.
Dinner with a View
Quince 100% European Linen Scoop Neck Midi Dress (M) // Sam Edelman Cora Slingbacks (8.5) // Coastal Fronds Toggle Bracelet // J.Crew straw clutch
Clean lines and breathable linen make this dress a great option for vacation evenings. I love the sleek, straighter silhouette, which feels a little more refined than a fuller skirt. The flattering scoop neckline, delicate spaghetti straps, and midi length create an elegant, understated look.
I wore this look to dinner in St. Lucia with strappy kitten-heel sandals and a straw clutch. To finish the outfit, I added a few simple accessories, including this fun gold-tone toggle bracelet with tropical-inspired charms that felt especially fitting!
Work Event
DKNY Sleeveless Side Ruched Sheath Dress (8) // Sam Edelman Bianka (8.5) // MAISON de SABRÉ The Medium Palais c/o // Jane Win Grace Pendant Necklace c/o
I purchased this dress for a wedding, but it would also make a polished work outfit. The clean sheath silhouette and subtle ruching are feminine and flattering while still feeling professional.
I styled it with neutral textured slingback pumps for a sleek, modern look, and carried a structured leather bag in this gorgeous shade of plum red that beautifully complements the indigo blue dress. Then I added a medallion pendant and a stack of bangles to complete the outfit.
Baby Shower
Donna Karan Faux Wrap Sheath Dress (10) // Dolce Vita Mylee Heels in Cream Heather (8.5) // Freja Caroline Bag in Oat // Jenny Bird hoops // Baublebar necklace // beaded stretch bracelets
This soft yellow sheath strikes just the right balance between polished and feminine, making it a great option for a baby shower, bridal shower, or any daytime celebration. The draped front panel creates the look of a wrap dress, while the side pleating gives it a flattering shape.
I paired it with ivory strappy heels to keep the look light and summery, and I added a stack of stretch bracelets in a mix of gold and chunky turquoise acrylic beads for a fun pop of color. A delicate faux-pearl station necklace fills the neckline perfectly without overwhelming the dress, and I carried an ivory east-west shoulder bag to keep the look cohesive.
Birthday Dinner
Donna Karan Twist Waist Sheath Dress (10) // Dolce Vita Mylee Heels in Light Tan Heather (8) // Olga Berg Ball Mesh Bag // Jenny Bird hoops // Baublebar necklace // beaded stretch bracelets
A birthday dinner is the perfect excuse to wear a dress that feels a little extra special, and this jade green sheath definitely fits the occasion. The twist detail at the waist creates a flattering silhouette, while the midi length and side slit feel polished and sophisticated.
I repeated the same jewelry I wore with the yellow dress—a delicate faux-pearl station necklace, beaded stretch bracelets, and simple gold earrings. But this time, I paired the dress with nude strappy sandals that blend seamlessly with my skin tone to help elongate the leg, which is especially flattering with a midi length dress. And a gold mesh bag adds just the right amount of evening glamour.
Afternoon Wedding
DKNY Sleeveless Side Ruched Sheath Dress (8) // similar sandals // YSL Kate (similar for less) // Jenny Bird hoops // Baublebar necklace // similar bracelet
Finally, this dress makes one more appearance! This is how I wore it to an afternoon wedding a few weeks ago. With dressier sandals, a sleek chain-strap bag, and a few elegant accessories, it takes on a completely different personality. I love finding pieces that can work for more than one occasion with just a few simple styling changes.
I hope these outfit ideas gave you a few fresh ways to style the dresses you already have hanging in your closet, or inspired you for an upcoming event on your calendar.
I’d love to know: Which look is your favorite, and where would you wear it? Let me know in the comments!
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