Dressing for Late Summer’s Best Occasions

The end of summer has a way of filling up with the good kind of plans. Birthday dinners, weddings, the very special vacation reservation you booked months ago. They arrive just as the light starts to change, and I wanted this edit to answer that exact moment: pieces special enough for the occasion, with enough richness to carry well past Labor Day. You'll find dupioni silk and textured jacquard, deep emerald and oxblood and chocolate brown, plus plenty of long sleeves for the evenings that finally turn cool. A few are true showstoppers, a few are quietly perfect, and nearly all of them will earn their keep again in October and again come the holidays.

• This sculptural gold bustier top and its matching olive-gold satin maxi skirt are so beautiful together for late summer evenings. Wear them as a set for a wedding, or split them up — the top with high-waisted trousers and statement earrings, the skirt with a starched white button-up and metallic sandals. The textured satin feels special enough for any event, and the column silhouette looks incredible. I'm wearing 100mm sandals in the photo above but wow I can't do that high of a heel. I own and love the 85mm version which I can comfortably wear for hours.
• This dress is the fit-and-flare you'll wear again and again — the dupioni fabric has such a beautiful sheen, and the full A-line skirt is incredibly flattering. The black is a forever piece that you can style with affordable gold heels, or these stunning embellished slingback pumps for a high-low moment. The oxblood bow-shoulder version feels festive without being fussy, taking you from August weddings right into holiday events.
• If you love long sleeves, this one is for you. This emerald silk maxi dress has the most beautiful drape and an oversized back tie that's incredibly elegant. Perfect with dramatic earrings and a statement clutch.
• Puffed sleeves and waist smocking make this floral long sleeve dress feel romantic and celebratory. It's a step up from the classic Nap Dress silhouette, perfect for dinner parties, showers, and festive late-summer gatherings.
• Long sleeves and a romantic floral print make this maxi dress in charcoal paisley perfect for the late-summer-into-fall transition. Wear with heeled sandals in August, and swap in pointed-toe boots in November. I love this dress for a similar look at a more wallet-friendly price.
• Purple dupioni silk gives this halter dress (15% off with STACIE15) the most gorgeous shimmer and texture. The crossed neckline is both elegant and bra-friendly (a rare combination!), making it ideal for weddings and evening events.
• Sleek and effortless, this cotton-silk flared dress has the most gorgeous movement thanks to the tiered asymmetrical skirt. (I own this dress in another color, and wear your larger normal size.) Pair with gold sandals now and velvet pumps later for an easy seasonal shift.
• Nothing says late-summer occasion like a dramatic silk gown. The ribbon detailing and cascading ruffles make this one truly special for weddings, galas, or formal dinners — I love it in this black floral (with this bag!) and I can't get over the red version. The crinkle chiffon and rich hues feel perfect for August through February events.
• This ochre dress is so versatile. I'd pair with a feminine slingback like this and a refined suede clutch in the same hue. And of course, this one is easy to dress down too!
• Such a pretty jacquard dress in the most flattering apricot shade. The textured floral fabric and square neckline make it feel polished for showers, weddings, and early autumn dinners. I'd pair with these blush-colored kitten heels and this burgundy satin bag that I own in another color, and love!
• Flutter sleeves and a flattering V-neck make this organic cotton maxi dress a great option for dinners, showers, and everything in between. Love the pockets, and it looks much more elevated than the price suggests.
• Savette's bags are quietly some of the most special pieces in my closet, and transition from day to night effortlessly. I'm obsessed with the artisanal knotted leather on this macramé pouch in mink — the little metal beads at the base add such a special touch. And for a pop of rich color, the plum suede pochette I mentioned before is perfection, with a structured silhouette and gold turnlock that feel very Art Deco.
• Deep moss green is such a beautiful hue for the shift into fall, and this cable knit top and matching silk charmeuse skirt make an incredibly chic set, reminiscent of Ralph Lauren Collection at a much better price. Lovely for a rehearsal dinner or an early autumn wedding, and both pieces work just as hard on their own.
• Erdem never disappoints, and this forest green pencil dress with three-dimensional pink flowers is absolutely breathtaking. A true showstopper for black-tie events, galas, or a very special dinner. (You can often find their dresses for 50-80% off on The Outnet (how beautiful is this!) and TheRealReal.)
• This long-sleeved satin dress is a dream for women of any age. I love the pewter hue paired with these drop pearl earrings and a metallic heel.
• A major splurge, but too lovely not to mention, this animal-print gown makes a statement at formal late-summer events. The square neckline and full skirt keep it feeling elegant rather than wild. Pair with simple black accessories.
• I'm wild about the embroidery on this shirtdress (20% off with StacieM20). The codes won't stack, but the discount applies to full priced items. Add a gorgeous pair of heels and a poppy red lip.
• Chocolate brown is one of my favorite hues for bridging seasons, and this sleek mini dress nails it. Wear with a big feather brooch, then swap in chocolate patent pumps come October.

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