August is that tricky time of year when you’re still living in summer mode but already eyeing the first signs of fall. The key? Pieces that transition seamlessly — think warm-weather staples that can be layered, timeless classics that never go out of style, and a few accessories that pull everything together.
Here are nine of my current favorites, plus how I’d style each one for now and later.
Mid-Rise Baggy Jean Bermuda Shorts — 9-Inch Inseam
These are the shorts you’ll actually want to wear all day. The relaxed fit gives them that effortless, borrowed-from-the-boys vibe, while the 9-inch inseam keeps things polished. Pair with a crisp button-down and sandals for August, then swap in ankle boots and a chunky cardigan when the weather cools.
NORMA KAMALI | Oversized Moto Jacket
An oversized moto instantly transforms even the most basic outfit into something edgy and chic. I love it thrown over denim shorts for a cool contrast or paired with wide-leg trousers and heels for a night out.
Women’s Original Tall Rain Boots
Rain or shine, these iconic boots are a must-have. Wear with bike shorts and an oversized sweatshirt for a sporty vibe now, or tuck in your jeans and add the moto jacket for a rainy fall day.
Havaianas Top Square Fusion Flip Flops
Sometimes simple really is best. These flip flops are sleek enough for city errands and comfortable enough for beach days. They’re the kind of shoe you’ll keep by the door all season long.
CEREMONIA | Guava Rescue Spray
Not all style is about clothes — this leave-in hair mist smells amazing and keeps your hair soft, shiny, and frizz-free. Toss it in your bag for on-the-go touch-ups, especially on humid late-summer days.
A warm, clean scent you can wear year-round. I love keeping a travel-size fragrance in my bag for a quick spritz before dinner or a last-minute meeting.
100% Organic Cotton Poplin Long Sleeve Button Down
A forever classic. Wear it tucked into denim shorts now, then layer it under sweaters or over turtlenecks in fall. You can even knot it at the waist for a laid-back weekend look.
Suede Leather Ankle Boots with Block Heel
The perfect shoe to bridge summer and fall. Wear them with shorts and a blazer now, then with jeans and an oversized sweater when the temperatures drop.
A hands-free bag is essential for busy days. This one’s big enough for your wallet, phone, and a few extras, but small enough to keep things feeling light and polished.
The Bottom Line
When your closet has a few versatile, well-made pieces, getting dressed becomes so much easier. These picks work together, mix with what you already own, and take you from late summer through fall without missing a beat.
