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The transition from Summer to Fall is always the toughest because, for what feels like the longest time, the weather fluctuates from hot as Hades to freezing cold, sometimes in one day.

I’ve compiled a few of my outfits to show you how I handle this transition.

One of my biggest rules for anytime I buy something is that I must already own items that would allow me to create at least three outfits with the new piece. This rule has stopped me from spending an unspeakable amount of money. (To see some my other rules, feel free to look back at my tips Shopping Tips.) So, a few of the pieces I’ve chosen to showcase have multiple outfits paired with them.

Rip Curl Flowered Skirt

Sweater I: Madewell

Sweater II: Nordstrom Rack

Sandals: Madewell

I love pairing shorts or skirts with long sleeved items. I think it provides an interesting twist to an outfits as well as a solution to the freezing in the morning, boiling in the afternoon conundrum. Adding sandals to the outfit also allows the wearer to feel cool, even when wearing a thick sweater, as well as allowing them to hold on to summer a little bit longer.

Sweater: Old BDG

This outfit is a little bit more conventionally transitional. But, I thought I would feature it because it does show the main way to combat in-between weather: layers. As with the other outfits, the sandals were chosen to provide some relief from the heat.

Striped Madewell Sweater

Tank: Old Nordstrom

Shoes: Target

This outfit is perfect for the days when it’s freezing in the morning but boiling in the afternoon. The sweater still adds that pop of color, even when tied around your waist and the shoes match almost perfectly with the colors in the sweater.

Shorts: Old Lucky Brand

Shoes: Target

This outfit is one of my faves because it still has that slight element of summer without hitting you in the face with it. The loose fit is super comfy and, although it’s a pretty cool outfit, it also includes warm, autumn tones, allowing you to feel like you’re dressed for fall (even when it’s still 90 degrees out).

Caslon Camo Shorts

I absolutely love these shorts. I’m not completely decided on how I feel about the camo trend. But, these shorts are easing me into it. They’re not so in your face about their camo print and I love their subtlety.

Sweater I: Nordstrom Rack

Shoes I: Old Target

Sweater II: Old Loft

Sandals II: Soludos

Again, I’m pairing sweaters with a shorter piece. I like these shorts best with grays, blacks, and navys. I chose pretty cozy pieces on top. And, although comfy, this outfit still looks fairly put together for one that involves shorts.

Sweater: Old Free People

Shoes: Supergas

I love the sportiness of this outfit, even though the only sporty aspect is the Supergas. But, I also love the contrast between the chunky turtleneck and the soft shorts. It combines the best parts of Fall and summer in Autumnal hues.

Banana Republic Shirt Dress

This dress can be worn in the heat and when it’s a little chilly out. It’s also perfect for work because it can be dressed up or dressed down depending on what you pair with it.

Shoes I: Kenneth Cole New York

Shoes II: Taryn Rose

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