Transitioning into Fall takes a little thought and planning, sure, but it shouldn’t be complicated. Our favorite outfits of the moment are all about simple pieces that are easy to assemble. Don’t know what to wear this month? We’ve got you covered with some inspiration from our designers and boutiques.

Loose shapes, ankle socks and boots — an effortless go-to.

Is there anything more classic than a white top and denim? Nope. But subtle slash standout details keep it fresh.

The classic white-and-denim combo works in so many ways — including oversized silhouettes.

Easiest way to look chic this fall? An oversized coat and a light turtleneck.

Playful prints and A-line midis are a perfect pairing.

Layer your fave black summer dress with a sweat top and slides for a cool transitional look.

The wide leg pant (one of our favorite pieces for fall) goes great with the contrast of a cropped jacket.

One thing to invest in this September? A long, comfy knit. Super versatile and casually sophisticated.

It’s all about comfort this season. We like to think of it as elevated lounge wear.

Best way to feel like you’re rocking your comfiest sweats but still look put together enough to hit the street? Tailored cuts and a trench.

Add big, bold patterns to make any outfit a little bit more interesting.

Still hanging onto those summer vibes? Just add a straw hat to fluid trousers and a dreamy top.

Catch those ’90s feels with high-waisted light denim and a tucked in tank.

September-ize your summer dresses by layering — just add a plain t-shirt and a fuzzy coat for the cooler weather.

Look on the bright side this season and stock up on colorful pieces to balance a usual sea of neturals.

How to add a little femininity to menswear-inspired silhouettes? Add a cute sandal.

Remember that candy-colored bomber jacket you had in high school? It’s back, with a modern twist.

A tailored coat in a neutral color like gray or navy is on our essential list and a perfect Fall topper for that summery LBD.

Our go-to Fall color palette also includes shades of gray. Then layer, layer, layer.

We love a good cropped pant as much as anyone, but pooling at the ankle in a straight leg jean has us giddy this season.

A classic khaki pant is always in season, but this time around it’s all about reinventing elegance.

Layer your blouse with a turtleneck for a vintage vibe that feels so now. And functional to boot.

Add in some texture — like a ruffled skirt — to give a classic sweater dress a little extra kick.

Show a little skin with a slit and a cropped sweater, while still keeping the rest of your body warm with long sleeves and a calf grazing hem.

Grunge never died. Keep its memory alive and well with an oversized denim jacket and a sheer, striped t-shirt.

Let the mule walk you all the way into winter.

Cutesy prints and girly details, like ruffles and bows, make for a sweet September.

Layer up your spring/summer staples. White pants after Labor Day and sweet hues will ward off those back to work/school blues.

An easy trench coat is a wardrobe staple for both fall and spring’s transitional months. Add personality with standout, look-at-me heels in an autumnal hue.

Fluid silhouettes in textural fabrics are an easy way to channel the Fall feels.