Saturday, August 27th, 2016

4 Dos and Don’ts of Transitioning Your Summer Wardrobe for Fall

4 Dos and Don’ts of Transitioning Your Summer Wardrobe for Fall

4 Dos and Don'ts of Transitioning Your Summer Wardrobe for Fall

Even though summer is ending, you don’t need to pack up all of your summer clothes! Here are some handy tips on how to transition your wardrobe between seasons without giving up all your favorite summer pieces.

Wait, don’t put those shorts into the Next Summer box! You know the box–or suitcase or corner, depending on your preference. It’s the one where your seasonal clothes go to die until next year. So long, crochet fringe bralet that I only got to wear twice. Hello, cardigans and sweaters.

I was born in the month of June, in Florida, to Zambian parents who had seen snow only once or twice in their lives. Suffice it to say I’m not a cold weather person. While others are looking forward to wrapping themselves in giant scarves and sipping hot lattes, I’m clinging desperately to my tank tops and short shorts. Luckily, just because summer is ending, doesn’t mean I have to give up all of my summer clothes! It’s easier than you think to transition your summer clothes into your fall wardrobe.

Shorts with a half sleeve blouse and over the knee boots


It’s the quintessential summer wardrobe item, but that doesn’t mean you have to pack them all up on the last day of August. Shorts can be paired with tights, over-the-knee and knee-high socks, and boots. Fabric makes a huge difference when wearing shorts in the fall–stick to denim or heavier fabrics, and leave the hot pants for next summer.

When wearing shorts in the fall, DO:

  • Pair them with tights, socks, or high boots to keep your legs warm
  • Wear heavier fabrics such as denim or leather
  • Pair with sweaters, long sleeve-blouses, or cardigans to keep your top warm


  • Wear light fabrics suck as chiffon or linen. If a cold breeze passes, you’re gonna feel every last degree of it.
  • Use bright prints such as floral or gingham. No matter how you pair them, they’ll look a little too out of place for the weather.

Maxi dress with a distressed knit sweater and combat boots

Maxi Dresses

Maxi dresses are the easiest way to look like you spent a lot of time putting yourself together. I don’t want to give up that ease quite yet! Maxi dresses are perfect for fall because all it takes is a sweater on top to transform it into a cute skirt and keep you warm. Fabric is especially important here–a lot of summer maxi dresses are made with lightweight materials that don’t retain any heat. A sweater can only do so much! Stick to solid colors or darker prints and leave the hibiscus print cutout maxi for next year.

When wearing maxi dresses in the fall, DO:

  • Pair them with a sweater or jean jacket that cuts off near or frames your natural waist. This will help prevent your shape from being lost under the layers!
  • Stick to solid colors or darker prints
  • Pair with cute ankle boots or booties for maximum warmth


  • Wear lightweight fabrics
  • Wear halter style dresses or ones with too many cutouts
  • Wear hibiscus or other popular summer prints

Crop top with high waisted button up jeans and faded denim jacket

Crop Tops

While the crochet fringe bralet might not be coming along, there are still plenty of other crop top styles you can try in the fall. Turtleneck, long sleeve, and box tee crop tops are ideal, but you can still utilize other cuts as well. Pair them with a high-waisted bottom that flatters your figure. If you have more of a pear or hourglass shape, high-waisted jeans or other fitted bottoms will accentuate your curves. For rectangle and apple shapes, an A-line midi skirt creates volume around the hips and balances out top and bottom.

When wearing crop tops in the fall, DO:

  • Wear turtleneck or long sleeve, as they go with just about anything. Tanks and strapless can be worn with a jacket or heavy cardigan.
  • Pair with a high-waisted jean or A-line midi skirt
  • Add a scarf to highlight the silver of skin showing at your midriff


  • Wear mid- or low- rise jeans. Too much midriff in fall looks counterproductive.

Strappy peach heels with a navy blue pencil dress and khaki blouse

Strappy heels

One big trend this summer was the resurgence of cage heels. These quickly became my go-to for every brunch and day party I went to. Whether or not you need to pack these up at the end of August depends on your style of shoe, but a lot of the more popular styles can be worn for another month or two!

When wearing strappy heels in the fall, DO:

  • Stick to styles like cage or geometric cut out
  • Get top heavy in what you wear, such as scarves or chunky sweaters
  • Wear them places where you will primarily be indoors–your toes will thank you


  • Wear sandy or bright summer colors–since the cut is out of season, the color should help it blend in.
  • Wear espadrilles or single-strap heels.

And there you have it! You can wear all your cute summer pieces a little bit longer. Rules are made to be broken, so let me know what you think about these dos and don’ts! Do you love shorts for fall, or do you think crop tops after Labor Day are a serious faux pas? As always, let me know your thoughts in the comments below!

Lots of love,

2 responses to “4 Dos and Don’ts of Transitioning Your Summer Wardrobe for Fall”

  1. Norma says:

    This is so detailed and informative!!! Great choices and great photos!!

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