And just like that, there’s a chill in the city again. The leaves are beginning to fall, temperatures are dropping, and our wardrobes are officially shifting into fall mode.

As difficult as it can be to say goodbye to summer, there’s something particularly exciting about dressing for a new season. The return of coats, boots, knits and thoughtful layers brings with it a fresh set of possibilities. Of course, early fall comes with its own challenge: mornings feel crisp, afternoons can still be surprisingly warm, and getting dressed somewhere in between isn’t always straightforward.

To make the transition a little easier, we’ve rounded up five early-fall outfit formulas that take the guesswork out of getting dressed. From casual days around the city to office hours and after-work plans, consider this your starting lineup for easing into the season with a little more confidence and a lot more style.

CROPPED TRENCH + V-NECK SWEATER LAYERED OVER T-SHIRT + JEANS + FLATS + SUNNIES

For errand days that turn into an afternoon around the city, this formula strikes exactly the right balance. The cropped trench and layered knit add polish without feeling too heavy, while jeans and flats keep things comfortable enough for wherever the day takes you.

LEATHER JACKET + JEANS + BELT + LOAFERS + SUNNIES

When the mood calls for something with a little more attitude, reach for the leather jacket. Paired with denim, loafers and a simple belt, it’s an easy combination that feels considered without trying too hard. Comfortable, cool and particularly good for those first crisp days of fall.

OVERSIZED BLAZER + T-SHIRT + PENCIL SKIRT + PUMPS + SUNNIES

Consider this the answer to workdays that don’t end at the office. The oversized blazer and T-shirt keep the pencil skirt from feeling too formal, while pumps bring the polish. It moves easily from meetings to dinner, drinks or an evening event without requiring an outfit change.

OVERSIZED BLAZER + T-SHIRT + MAXI SKIRT + FLATS + SUNNIES

For days when denim simply isn’t calling your name, a maxi skirt offers an equally easy alternative. An oversized blazer gives the softer silhouette some structure, while a simple tee and flats keep the look grounded. It has enough personality for everyday plans while still feeling polished enough for the office.

FUNNEL NECK COAT + T-SHIRT + TROUSERS + HEELS + EVERYADY BAG + SUNNIES

Cozy doesn’t have to mean predictable. A funnel-neck coat paired with a simple T-shirt and tailored trousers creates a quietly confident look that feels both relaxed and refined. Add heels and an everyday bag, and you have a formula that can handle everything from the morning commute to whatever comes after.