Transitioning from Summer to Fall ~ Shorts

Over the last week, I’ve been sharing my transition tips for styling your way from summer to fall. All you need are a few autumn staples, and you can easily transform your summer favorites (like I did here and here) into fall-ready looks. But what about when the weather isn’t cooperating? What about when those late September days feel a little less “Indian” and a little more “Summer”? It might not be time to put those shorts away just yet!

But if you’re like me, you might be getting a little tired of the summer uniform. Shorts. Tank top. Shorts. Tank top. Fortunately, you have plenty of ways to style your shorts on those warm September days in a way that’s distinctly fall.

A New York Love Affair :: Styling Your Short for Fall

When styling your shorts for those off-seasons, I stick to one simple guideline: one or the other … legs or arms. It works for autumn or spring. In this case, since I chose to bare some skin on my legs, I balanced out the look by covering my arms with a jacket. On the other hand, if I had chosen to wear pants, I’d be more likely to pair it with a tank top or tee.

Another subtle but easy transition tool is footwear. As much as I love my sandals in the summer, after Labor Day I dutifully pack them away. Covering your feet up with a sweet pair of Jack Purcells or Keds is an great way to put a little ‘back to school’ in your step, while still staying (and looking) cool on a warmer day.

A New York Love Affair :: Styling your Shorts for Fall

My last little tip has to do with colors. Adding blacks, browns and dark greens to your outfit is a fantastically simple way to give your look a fall makeover. Like this army green jacket – it’s three-quarter length sleeves and lightweight feel make it the perfect transitory piece, and yet it’s color allows me to wear it well into the autumn months.

A New York Love Affair :: Styling your Shorts for Fall

A New York Love Affair :: Styling your Shorts for Fall

A New York Love Affair :: Styling your Shorts for Fall

A New York Love Affair :: Styling your Shorts for Fall

Don’t stress out when your day doesn’t fit perfectly into one season or another. Mother Nature is constantly changing things up, and it’s important to have a wardrobe that can keep up! With a few easy tricks, you can dress for whatever she decides to throw at you. And stop complaining, winter will be here before you know it, and you’ll be WISHING for shorts weather!

For more transition tips, check out last week’s posts ~ styling your white jeans and maxis for fall.


Shorts :: H&M
Shirt :: c/o Color Me Courtney (loving these tees)
Jacket :: Forever 21 (similar)
Bag :: Kate Spade c/o Color Me Courtney (love this and this)
Shoes :: Converse
Sunglasses :: Coach (almost exact)
Watch :: Michael Kors (similar – on sale!)
Bracelets :: Wantable and Lizzibeth
Lips :: MAC “Girl About Town”


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