3 Easy Steps to Transitional Dressing

Last Updated on April 16, 2026 by Betsy Ramsey

With September afoot, it’s time to start thinking about how to transition our wardrobes for the fall season.πŸ‚ Now, don’t panic! I won’t make you put away your sandals and sundresses just yet. But bookmark this article and, as the days cool, start implementing these 3 easy steps to transitional dressing.

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3 Easy Steps to Transitional Dressing

1. Change Up Your Footwear

When transitioning my summer wardrobe to fall, this is often the first step I take. Swap out sandals and espadrilles for heavier footwear like booties, loafers, oxfords, or chunkier platform sneakers.

It works well as a nod to the coming season because it doesn’t really affect your temperature on warmer, early-fall days.

2. Swap Straw for Suede

The second step is to swap out your straw, bamboo, and canvas accessories for those in suede, wool, tweed, or corduroy. Similar to changing up your footwear in the first step above, this is an easy step to incorporate when it’s still pretty warm out.

3. Layer

Lastly, start layering. This is the Hail Mary step for when it’s getting noticeably cooler but you still want to wear those sundresses and lightweight tops! Get creative here. It’s common to layer a sweater or jacket over a blouse, but try layering a tee beneath a sundress or looser-fitting short-sleeved top.

Vests, blazers, heavier-weight shirts, scarves, and ponchos make fantastic layering pieces for your top half. For your lower half, try adding tights or leggings. If you enjoy a trendy vibe, pair calf-length socks with heels or chunky platforms for a look on the 2024 runways.

Transitional Dressing Examples

Using the three easy steps above, we can transition a summery sundress to work for the start of fall. First, change from delicate sandals to cute booties. Next, swap your straw bag for a suede one and your straw hat for a felt one. Lastly, add a cozy, cropped sweater over the dress when temperatures drop!

3 Easy Steps to Transitional Dressing

Transition a summery top and jeans to fall by replacing your accessories with rich, chocolate-brown pieces and adding a cozy pumpkin-colored cardigan.

Lastly, change up a jumpsuit by incorporating chunky footwear and layering a white tee underneath. As temps continue to drop, add a denim barn jacket with a sherpa or corduroy collar.


Hopefully, you won’t need to incorporate these tips too soon! πŸ‚

Until next time…keep cultivating a simple, stylish, and satisfying life!

As August winds down, it's time to start thinking about transitioning our wardrobes for fall with 3 Easy Steps to Transitional Dressing!

Author: Betsy Ramsey

Elizabeth "Betsy" Ramsey is an accomplished independent traveler and the content creator behind Natty Gal. She has visited 64 countries and 34 US states, to date. Betsy encourages readers to travel independently, by sharing tips to reduce trip-planning stress, increase confidence, and maximize their travel experiences. Betsy was born and raised in Northeast Ohio and currently lives there with her husband and Bichon-Frise, Dolce. Follow Betsy on social media @nattygaldotcom.

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