As much as I love summer, I always get excited to dress for fall. The transition season is a bit of a challenge, though, isn’t it? The kids are getting ready to go back to school, Labor Day will soon be upon us, and the stores are filling up with fall styles and warm, vibrant colors, but the weather won’t catch up for a while yet. Depending on where you are located, you can expect some hot days well into September.

This is a great time to put together new outfit combinations and try new trends. I tend to put away my lighter fabrics and and white sandals after Labor Day, but I keep out my white jeans (a fun transition piece, now that the white-after-Labor-Day rules are passé) and denim shorts, which can carry me well into fall. I’ll also start to bring in some deeper, richer colors that remind me of fall, and I find myself opting for ballet flats or ankle boots rather than sandals.

Payless invited me to check out their new fall shoes and put together a couple of outfits to show you how I transition my style from summer to fall, and I needed no more encouragement! I headed over to my neighborhood Payless to see what they have in their fall lineup. Suffice it to say, if you’re looking for affordable styles to transition your wardrobe from summer to fall, Payless has you covered. At one point, I had about 5 pairs of shoes I was trying to decide between, but I came home with these Charm Skimmers in grey and these C Ballet Flats in cognac.

For those early fall days when the weather is still quite warm, I’ll still be wearing shorts and t-shirts, but I’ll opt for bolder colors and heavier fabrics. These skimmers are the perfect casual shoe to carry those summer outfits into fall. They are lightweight and comfortable with a sporty vibe, and the padded insole is like walking on clouds.

They are the perfect compliment to a casual outfit like this one.

Jean shorts and a t-shirt are always in style. In the warmer months, I would wear sandals or flip-flops with this outfit, but as we head into fall, these Charm Skimmers are the casual perfect transition shoe.

As the weather gets cooler, I’ll start to wear more fall colors. Often the mornings are chilly but the afternoons are warm, so long pants and short sleeved tops are my go-to. I love mixing combinations of navy, grey, army green, and brown in the fall.

I have these C String Tie Ballet Flats in blush and I’ve enjoyed them, so when I saw them in cognac, I snatched them right up. Cognac is such a great color for fall. It goes with just about everything, even black.

For this post, I paired a grey t-shirt with army green cargo skinnies. I chose my accessories to tie in the brown and gold from the cognac flats. I think this is the quintessential summer-to-fall transition outfit.

I’m starting a new series next month called 26 Days of Fall Fashion, where I’ll share a different fall outfit every day. I’m looking forward to the challenge, and I hope it gives you some new ideas as we navigate this transition season.

This is a sponsored conversation written by me on behalf of Payless via RhythmOne. The opinions and text are all mine.

linking up with BonBon Rose Girls, Sincerely Jenna Marie and More Pieces of Me