Transitional Fall Looks
What to Wear When It’s Technically Fall, But Still Warm Outside
The leaves are changing, pumpkin spice is back, and your calendar says it’s fall—yet the weather still feels like summer. Dressing for this in-between season can be tricky, especially when it’s too warm for heavy sweaters but too cool for your favorite sundresses. Luckily, transitional outfits offer the perfect solution. Whether you’re pulling from your summer wardrobe or diving into vintage fall staples, these looks will help you stay comfortable and stylish as the temperatures gradually dip.
1. Tall Boots with Denim Shorts
One of the easiest ways to transition summer staples into fall is by pairing them with fall essentials. Tall boots, whether they’re leather or suede, look incredible with denim shorts. Add a light knit or a cropped jacket to complete the look, keeping things both cozy and cool.
Outfit Inspiration:
Vintage high-waisted denim shorts paired with a chunky sweater and knee-high boots.
Add an oversized blazer or leather jacket to keep warm on breezy days.
2. Long Skirts with Long-Sleeve Tops
Long skirts are perfect for fall—they offer coverage and warmth while still being stylish. Pair them with fitted long-sleeve tops to balance the silhouette, or try a more relaxed oversized top for a laid-back vibe.
Outfit Inspiration:
A 70s-inspired maxi skirt with a fitted turtleneck and ankle boots.
Mix textures with a silk skirt and a cotton long-sleeve for a blend of comfort and elegance.
3. Layering Silk, Linen, and Cotton
Layering lightweight materials like silk, linen, and cotton is a subtle yet effective way to add dimension to your outfit without overheating. These fabrics create a breathable, comfortable look that’s perfect for those warmer fall days.
Outfit Inspiration:
A vintage silk camisole layered under a linen blazer, paired with wide-leg pants.
A cotton button-up shirt under a silk scarf and linen vest for a chic, layered look.
4. Vests: The Versatile Layer
Vests are a great way to add personality and warmth to any outfit, without the bulk of a full jacket. From sweater vests to denim and leather, they’re an easy layer to throw over your fall looks.
Outfit Inspiration:
A 90s denim vest layered over a flowy blouse and straight-leg jeans for a retro vibe.
A knitted sweater vest over a collared shirt, paired with tailored trousers for a preppy look.
5. Short Skirts with Oversized Sweaters
Fall is all about playing with proportions, and nothing does this better than pairing short skirts with oversized sweaters. It’s the perfect combination of casual and chic, keeping you warm up top while still showing off your legs.
Outfit Inspiration:
A vintage mini skirt with a slouchy, oversized knit sweater and ankle boots.
Layer tights or knee-high socks under your skirt as the temperatures drop for added warmth.