Now & Later: What to Wear in August and Beyond

Stacie Flinner x Tuckernuck Eyelet Caftan-11.jpg

I can’t believe it’s already August! This time of year I find myself slowly transitioning my wardrobe from summer brights to warmer neutrals and earthy tones. Even if I’m still wearing a crisp cotton dress it will likely be in a richer color, or I’ll pair it with more textural accessories as we look towards fall. Whether you’re wishing for an endless summer and want to extend the life of your favorite sundresses, or can’t wait for sweater weather and are on the hunt for new fall styles, I’m sharing some transitional outfit ideas that feel right for this moment.

I’ve been saving this dress for an upcoming weekend getaway, but saw it’s selling fast so wanted to share it now so you can snag for your own August adventures! (The cut is generous so I sized down!) Some dresses just make you feel amazing and this eyelet caftan is one of those dresses. The perfect color, weight and silhouette for those in-between days as we transition from summer into fall. Wear with ivory or white accessories now through Labor Day, and swap in rich caramel leathers or suedes in September to effortlessly adapt this dress to the changing seasons. (I’d say it’s especially smart for my Southern girls, who want something airy that can also feel autumnal with the right bag and shoes.)
Similarly obsessed with this green eyelet midi skirt. I love how the army green toughens up the delicate embroidery, and this skirt would look especially chic with an oatmeal cashmere cardigan and suede pumps. (This rust skirt would also look amazing with that sweater + shoe combo!)
Wear this luxurious woven leather bag with your classic white and denim pieces now, and with neutral cashmere pieces later.
A classic breton stripe top is a year round staple, and this yummy bordeaux version is perfect for wearing with white denim now and tweedy blazers later.
The metallic threads in this ochre floral dress make it a festive for late summer parties or date nights. Wear with flats now and heeled knee high boots later.
The embroidery on this skirt is just WOW. Style with a white tank and barely there strappy flats for summer, and a chunky knit and blue suede shoes for fall.
Fall is loafer season and I find that the best styles always sell out early. I own and love these mules for everything from running errands, to days at the office, to long-haul flights. I sized up 1/2 size as I do with all mules and you can get 25% off your order through 8/8 with secrete code “25FORYOU”.
I love the autumnal hues in this silk scarf (currently 60% off!) which adds interest to jeans and a button down shirt now, and wool wrap coats and sweaters later. Get 25% off your order through 8/8 with secrete code “25FORYOU”.
Dark florals are perfect for this time of year, and I love how this black number can be dressed up or down. (Would look fab with the wedges below!)
I have these slingbacks in a kitten heel, but at 50% off the 85mm leopard version is also tempting.
I love belts for transitioning summer dresses into early fall looks. This black skinny belt is brightened by the gold clasp, and I’d pair with these black wedges – on sale! (a few sizes on major sale here!). This combo effortlessly transitions many summer sundresses well into autumn. (Another take on this strategy can be found here!)
This splurgey tote is such a gorgeous color and perfect for a late summer weekend getaway.
I discovered the brand Toccin while putting together this post, and am very drawn to the way they use stripes – preppy but unexpected! This maxi dress specifically caught my eye.
Take any straw summer bag, and wrap the handle in this silk twilly to instantly extend it’s life into fall. (You can always get 20% off at Fleur Sauvage with code “Stacie20”!)
I own an past season version of this silk floral number – which has such a flattering and forgiving shape.
I love a good shirtdress and this one (worn here) works well from early spring through fall simply by swapping around your accessories. It’s 25% off through midnight tonight (August 7th!) and also available in a pretty striped version.
I saw these stunning jacquard heels on the production line when I was in Italy earlier this summer. The perfect pump 85mm are truly the most comfortable heels I own, and I get a ton of use out of my jacquard versions which are an easy way to add interest to solid colored dresses. Get 25% off your order through 8/8 with secrete code “25FORYOU”.