When the seasons change, your wardrobe deserves a refresh—but that doesn’t mean starting from scratch. Classic fall staples like leather jackets, sweater dresses, jeans, and tall boots are reliable, but this season, a few clever styling tricks can instantly transform your look. Comfy yet chic, these five outfit ideas—drawn straight from Fashion Week street style—show how simple tweaks can make your transitional wardrobe feel fresh and inspired.

The key trend this fall? Effortless style. Embracing trends doesn’t have to be complicated. Mixing textures, reimagining how you wear a classic piece, or adding unexpected layers can completely shift your outfit’s vibe. A sheer skirt paired with a chunky knit, a tied shirt at the waist, or swapping a button-down for a polo under a blazer—these small changes make a big impact. Use these ideas to guide your seasonal shopping or simply reinvent the pieces you already love.

1. Sheer Skirt + Chunky Knit

As the weather cools, transitional dressing is all about balancing light and cozy pieces. Pair a semi-sheer skirt with a chunky cardigan or rollneck sweater for an outfit that’s simultaneously feminine and relaxed. This combination keeps your look fashion-forward without feeling overdone. Complete the ensemble with ballet flats or sleek sneakers to stay comfortable while walking around town, making it perfect for both casual and slightly dressy occasions.

2. Dress Over Pants

The layered dress-over-pants trend is back and ready to elevate your fall wardrobe. Throw a flowy dress over high-rise trousers or straight-leg jeans for a look that’s both creative and practical. For an added style boost, try wide-leg jeans paired with a structured jacket to lean into a maximalist, statement-making vibe. This approach lets you stretch your wardrobe while experimenting with unexpected layering combinations.

3. Sporty Meets Sleek

Leather or faux leather separates are perennial fall favorites, but this season, the trend takes a playful, sporty turn. Think leather skirts or pants paired with rugby shirts, athletic-inspired shorts, or windbreakers. This juxtaposition of sleek and casual pieces adds a modern, preppy edge to classic leather, creating looks that feel both effortless and intentional. It’s a perfect way to inject personality into your fall staples.

4. Office Prep

Menswear-inspired shirts, ties, preppy polos, and box-pleat skirts are gaining traction this season, offering a polished yet approachable aesthetic. Mix tailored essentials with playful preppy items to create outfits that work just as well for the office as they do for weekend outings. Top it off with a trench coat for a refined outer layer that keeps your look on trend without trying too hard. This is fall style for the modern professional—smart, stylish, and versatile.

5. Accentuate the Waist

A simple styling trick spotted on the streets of Copenhagen, New York, London, and Milan? Cinching pieces at the waist. Adding a scarf, belt, or knotting a long-sleeve shirt or sweater transforms ordinary layers into standout transitional outfits. Try it over a slip skirt for an effortlessly chic look, or give your classic jeans-and-tee combo a fresh twist. This easy tweak adds structure and visual interest without any new purchases, making it a fail-proof way to elevate your fall wardrobe.