5 Easy Ways to Transition Your Summer Wardrobe to Fall

August 27, 2021

A guest post from Jennifer Mary of Everyday Style who was featured on episode 8 of The Mom Shuffle podcast. Haven’t had a chance to listen to our awesome episode with Jen? It’s a fun one! Find it here.

With lazy summer days rapidly disappearing, most of us are turning our thoughts to fall. Pumpkin Spice is in everything from lattes to Cheerios, “It’s Fall, Y’all” pillows are everywhere, and  Bath & Body Works’ “Sweater Weather” candle is back (best scent ever).

It’s easy to be lulled into thinking that sweater weather is coming to your wardrobe soon, too. But if you’ve ever spent a miserable early September day in an outfit that was made for late October, you know that booties, layers, and sweaters are still a ways off.

So, what’s a girl to wear when her heart says fall but the temperature still says summer? Read on to learn how to create a wardrobe that has you looking and feeling, seasonably appropriate!


Ideal Fall vs Actual Fall

Fall is, hands-down, inarguably, fashion’s best season, and we all want to break out our new booties and jeans, and layer up with cozy cardis. But what happens is, we only buy those things and then struggle to get dressed for the first half of the season. We’re frustrated that we don’t have anything to wear, and mad that the weather isn’t letting us wear the great things we DO have. Here’s the problem: We shop for ideal fall, not actual fall.

Ideal fall looks like this: Pumpkin patches. Falling leaves. Hot apple cider. A chill in the air. Plaid.  (I know, I can’t wait for it, either)

Actual fall looks like this: 84 degrees. Humid. Cool mornings, hot afternoons. Sweaty. Yeah, it’s a lot less Pinterest-worthy.

But the reality is, actual fall, depending on where you are, can last until mid or late October. So you spend the majority of fashion’s best season struggling to get dressed.

Once you recognize that you have to plan for actual fall as much as ideal fall, getting dressed gets a whole lot easier.

Then, follow these steps to slowly transition from end of summer to ideal fall, easily and stylishly.


Swap Colors

The easiest thing to do in any seasonal transition is to look for weather-appropriate silhouettes in the next season’s color palette. For fall, that means transitioning away from light and bright to richer, more saturated hues. Summer 2021 already gave us lots of colors that have traditionally been used in fall, so your wardrobe may already have a head start on this one.

See a few warm-weather styles in cool weather colors to get you feeling fall here.


Switch up Your Shoes

There’s a whole lot of time between flip-flops and Uggs, and another easy way to slowly move your summer wardrobe into fall is to switch to shoes with more coverage without going full-on boot. For example, perforated booties, or those with open toes, are more fall-ish than sandals, but they’re easier to style for warm weather than a solid, closed-toe version.

Pay attention to colors, too. Tan or taupe booties will be easier to wear in actual fall than a black version might be if you’re still wearing lighter, brighter colors.

Check out these actual fall shoe styles on the Everyday Style blog here.


Look for Light Layers

Later in the season, layering is easier because you’re likely to wear the same outfit all day long. In actual fall, you either need to find very lightweight layers, to give you that ready-for-fall look, even when it’s hot, or you need to be prepared to shed your top layer as the day goes on.

All season long, we’ve been seeing kimonos and ruanas that are the perfect weight to turn your summer looks into fab fall options.

Here are a few we love, along with some lightweight cardigans, on the Everyday Style blog.


Swap Silhouettes

A long sleeve top with shorts isn’t exactly a new concept–that’s what we do when the weather turns a little chilly, right? Make that idea look more current by keeping your tanks and short sleeve tees, and swapping shorts for pants instead. Paper-bag waist pants and a tank is a more modern look that straddles the seasons well.

Check out these lightweight pants for inspiration on the Everyday Style site.


Switch to a Transitional Handbag

If you’ve been rocking your straw bag all summer long, this is a good time to pack it away for the season. Before you bring out a heavy black bag though, move through early fall with a transitional handbag.

Just like with your shoes, look for lighter colors like tan or taupe. If you’re ready to bust out your black bag, add a colorful crossbody strap to lighten up the look.

The Everyday Style blog features a few handbags perfect for actual (and ideal) fall.

We hope these tips help you enjoy fashion’s best season, rather than impatient waiting for actual fall to start…or sweating through the day in your new fall clothes, mad that the weather isn’t cooperating!


You can find more great tips, helpful guides, and excellent podcast episodes from Jen and the Everyday Style team all year long, on their website at

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