20 of August’s Best Dresses

August is one of my favorite months for getting dressed because you can still embrace all the ease of summer while starting to reach for richer colors, beautiful prints, and pieces that hint at the season ahead. This month’s dress edit is full of exactly that: romantic florals, polished shirt dresses, textured knits, and deeper shades of wine, rust, olive, and navy that feel right at home now and will carry beautifully into fall. Many of these are the kind of dresses you can wear with sandals today, then style with boots, a cardigan, or a blazer in September and October. Below, I’m sharing 20 of the best dresses I’ve found for August, from easy everyday options to a few special pieces for dinners and late-summer occasions.

• This paneled floral midi dress (size down) in cotton-silk is the essence of late summer romance. The mixed floral panels are so charming. Pair with block sandals and a bucket tote now, and knee-high boots and a cardigan in September.
• For an effortlessly elegant option, this wine-colored open knit maxi dress with scalloped trim works year-round. Style with brown suede sandals now and tall boots with a blazer come October.
• Paisley silks are a favorite as the weather cools, and the cascading ruffles on this mini dress are so romantic. I'm also obsessed with this bias-cut silk midi dress in the most beautiful moody paisley. Either would look stunning with these chunkier suede sandals and knee-high boots later.
• How chic is a denim dress for early fall? This Italian cotton fit-and-flare midi has the most polished silhouette. Dress it up with ballet flats and a structured bag for the office, or pair with strappy sandals for casual dinner parties.
• A striped sweater dress (on sale!) in green is the kind of piece I reach for when I want to look polished with zero effort. The square neckline is so flattering. Great with mules now and boots in the fall.
• Ann Mashburn's Liberty print shirtwaist maxi is endlessly versatile, with a nipped waist and on-seam pockets. Looks gorgeous with flat slides now and knee-high boots come October.
• This vibrant paisley floral halter maxi (comes in regular and petite!) is perfect for a vacation dinner or garden party. The colorful print practically accessorizes itself, just add simple sandals and you're set.
• Dôen's paisley prints bridge the seasons beautifully, whether you opt for this silk-blend paisley dress in the most beautiful muted tones, or this plum smocked cotton midi dress. This ruched midi offers paisley perfection at a great price point.
• Nothing says effortless vacation dressing like this silk dupioni caftan dress (15% off with STACIE15) with a v-neck and button front. The side slits add easy movement, and the bandana-inspired print is gorgeous with suede t-strap sandals and stacked bracelets.
• Stunning white embroidery against rich wine-hued cotton makes this puff-sleeve midi a showstopper. The square neckline and fitted bodice are so flattering. Perfect for garden parties, church, or a special dinner.
• Mughal palace-inspired embroidery turns this linen bustier dress (on sale, I wear a size 40) into something truly special. Wear it to a late-summer wedding with statement earrings and strappy heels. I have the maxi skirt (also on sale) and have been reaching for it often since the pattern is so versatile.
• Frances Valentine's wrap dress in olive is one of those rare pieces that works at the office, at dinner, and on the weekend with just a swap of your shoes. The belt tie cinches beautifully, and the midi length is endlessly versatile with heels or flats.
• Already thinking about fall? This space-dyed striped knit midi in warm rust tones is incredibly flattering with its fit-and-flare shape. Pair with suede sandals now and boots later.
• Zimmermann's retro-inspired polo sweater dress has such beautiful tonal depth in the mouliné ribbing. The polo collar adds a preppy touch. I'd wear this with loafers and gold hoops for a fall lunch.
• I love the corset-inspired bodice on this blue paisley twill dress. The structured fabric and removable belt create such a flattering silhouette. (I got my usual size.)
• Wiggy's best-selling cotton dress in this season's tortoiseshell print is such a unique take on a neutral. I love the adjustable ties at the bust, and it transitions beautifully from day to evening.
• Classic blue and white stripes on this shirt dress (20% off with StacieM20) make it a wardrobe workhorse. Add cognac leather accessories now, then throw a camel sweater over the shoulders when it cools down.
• Rich red florals make this midi dress feel like the perfect bridge between summer and fall. I'd wear it now with sandals and later with knee-high boots and a cozy cardigan layered over top.
• Every detail on this navy cutwork dress is extraordinary. The cutwork embroidery creates the most gorgeous texture. A showstopper for a special dinner or cocktail party with gold accessories.
• Can you believe this gorgeous floral maxi dress is from Gap? The smocked waist and puff sleeves are so flattering. Perfect with sandals for farmers market mornings or a casual dinner out.
• If you have a fall wedding on the calendar, this watercolor-print gown is absolutely breathtaking. The drop waist and flared paneled skirt bring just the right amount of drama. There's also a shift version if you love the print but want something more everyday.

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