Fall on Top, Summer on the Bottom: Transitional Outfit Ideas

It might feel like fall in the morning, summer by lunchtime, and fall again once the sun goes down. That’s Wisconsin for you!

You don’t have to choose between dressing for the new season and staying comfortable in the heat. Pairing fall-inspired tops with shorts is an easy way to start wearing your new arrivals now while getting a little more life out of your summer wardrobe.

Here are two transitional looks we styled for This or That LIVE.

Outfit One: Cozy and Casual

The Theresa Ribbed Sweater Top adds cozy texture without the bulk of a full sweater. Its cap sleeves make it comfortable enough for a warm afternoon while still giving the outfit an early-fall feel. It’s available in sizes S–3X.

We paired it with the Hanna Denim Boxer Shorts by Judy Blue, available in sizes S–3X. Their relaxed boxer-inspired fit keeps the outfit casual, comfortable, and easy to wear.

The Audrey Circular Satchel Crossbody Bag in navy finishes the look with a subtle pop of color.

This is an easy outfit for running errands, meeting a friend for lunch, or enjoying one of those days when the weather can’t make up its mind.

Outfit Two: Polished and Relaxed

The Jane Blouse brings a rich navy color and feminine ruffle detail into the look. It feels polished and fall-ready without being too warm for the end of summer. The Jane is available in sizes S–3X.

We styled it with the Oatmeal Linen Shorts, available in sizes S–XL. The light neutral color balances the navy beautifully, while the cotton-linen fabric keeps the outfit relaxed and breathable.

The Veronica Floral Embossed Wallet adds texture and a pretty floral detail to complete the outfit.

This look would be perfect for lunch, a casual day at work, shopping, or anywhere you want to feel put together without looking overdressed.

The Best of Both Seasons

Transitional dressing doesn’t require an entirely new wardrobe. Try pairing richer colors, ribbed textures, and sweater-inspired tops with the shorts you already love. As the weather cools down, you can swap the shorts for jeans and keep wearing the same tops throughout fall.

Which look would you choose: cozy and casual or polished and relaxed?

Shop these pieces online or stop into Uptown Girl Beauty & Boutique to try them on!