The shift from long summer days to crisp fall mornings can make getting dressed a little tricky. One day it’s sunny and warm, the next you’re reaching for a sweater. That’s where transitional pieces come in—the wardrobe staples that bridge the gap between seasons and keep you feeling stylish no matter the forecast.
At Dress Up, we’ve rounded up the must-have items that make moving from summer to fall seamless (and chic!).
1. Lightweight Sweaters
When it’s cool in the morning but warm by afternoon, a lightweight knit is the perfect solution. Pair it with denim shorts on hotter days, then swap for jeans or a midi skirt when the temps drop. Oversized fits give you that cozy fall vibe without being too heavy.
2. Midi Dresses
Midi dresses are the ultimate year-round piece. In late summer, style them with sandals or sneakers. Once fall hits, add ankle boots and a denim jacket—or even layer a sweater on top to make your dress double as a skirt.
3. Shackets & Light Jackets
A shacket (shirt + jacket) is one of the easiest layering pieces for transitional weather. Toss it over tanks and tees when it gets breezy, or wear it open with leggings and sneakers for a casual-cool look. Even throwing on a light jacket or denim jacket remains a timeless option.
4. Maxi Skirts
Maxi skirts in neutral or darker prints make an effortless transition into fall. Pair with tanks now, then switch to chunky knits or cropped sweaters as the season changes. Bonus: they look great with both sandals and booties.
5. Neutral Basics
Every transitional wardrobe needs reliable basics—think camis, tanks, and fitted tees. These layering essentials pair under sweaters, cardigans, and jackets, making them the foundation for countless outfits.
6. Ankle Boots
Say goodbye to flip-flops and hello to ankle boots. They instantly bring a fall feel to dresses, skirts, and jeans—even if the weather hasn’t fully cooled down yet.
Shop Transitional Styles at Dress Up
The secret to dressing between seasons is all about layering and versatility—and our new arrivals are packed with styles you can wear now and later. From lightweight sweaters and jackets to midi dresses and maxi skirts, Dress Up has the transitional pieces your wardrobe is waiting for.
Step into fall in style without skipping a beat.

