How To Style A Fall Transition Outfit High or Low

It’s time to transition your wardrobe from summer to fall! September is a combination of warm summer heat and cool fall breezes so you need be prepared to dress for both seasons. Here’s a simple way to style a fall transition outfit high or low.

Style Your Fall Transition Outfit High or Low

The summer to fall transition is actually one of the easiest times of the year to style an outfit. You can wear a simple tee and jeans with an oversized cardigan. Then slip on a pair of slide shoes (without socks) and you are set for the entire day. Of course you can invest in high-end designer fashion pieces, or seek out low priced prices that look quite similar. I did the research and found both high and low for you. Or you can always mix high and low together for what is truly high low styling. If you wear one or two items from the “high” side, it will elevate your entire look.

The Oversized Cardigan

The day may start off warm but when it cools off you’ll be happy to wrap yourself in a cozy oversized cardigan. This Max Mara Corona Cable Cashmere Cocoon Cardigan in tobacco is the perfect piece to add to your transitional wardrobe. The color is on-trend for fall and it is totally neutral. This color looks amazing with bright colors like cobalt, violet or magenta and works with pastels, too. However, if you don’t want to invest $1,150 in one sweater you may like this BP. Open Stitch Cardigan in rust for only $49 from Nordstrom.


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The Basic White T-Shirt

A short sleeve v-neck tee is a wardrobe essential, and a must-have for the summer to fall transition. James Perse makes some of my favorite luxury tees. I have found the fabric and fit of James Perse tees to be divine. This white James Perse Casual Tee with a V-neck is well worth the investment of $85, but you can also get a similar look with this Madewell Whisper Cotton V Neck Pocket Tee for only $19.50. It may be hiding under the sweater for the most part after all.

The High Waist Skinny Jeans

September the best time of the year to add a new pair of jeans to your wardrobe. The bulk of the cardigan in this outfit calls for a pair of skinny jeans to balance the silhouette. A pair of light washed high waist jeans like these GRLFRND Karolina High-Rise Skinny Jeans for $228 are ideal. But you can get a similar look with these H&M Super Skinny High Ankle Jeans for $19.99. They are less than 10% of the designer jeans price!

The Exotic Print Slide Loafers

This is when the in-between weather gets fun, because you can wear in-between shoes. Open back slide loafers are so easy to slip on and wear. Why not get a pair of Gucci Princetown Slippers in a zebra-print hair calf? These shoes are an investment at $950 but you can wear them year after year and for all seasons. Alternatively you can get a similar look for less with these Linea Paolo Annette Loafer Mules in a python print. They are now only $65.96.

The Gold Buckle Belt

Nothing pulls together a casual look better than a belt. This iconic Gucci “Double G” leather belt in black is a good investment at $460. Lauren owns this designer belt and if you look at how often she wears it on Instagram, you know she certainly gets an ideal cost-per-wear. But if you want a simplified version, this Topshop Leather Belt for $35 will do the trick.

Transition From Summer To Fall Styling Tips

    1. Wear pieces from both seasons. This may sound like a no-brainer but it works. Don’t pack away all of your summer t-shirts! I usually keep several black and white t-shirts in my wardrobe year round. They work as perfect layering pieces under oversized sweaters and even woolly jackets. If a day between seasons becomes suddenly hot, you can keep your cool in your t-shirt. Other summer pieces to keep wearing are canvas sneakers, peasant blouses, and white jeans.
    2. It’s a wrap. The transition to fall is the time to bring out the jackets, blazers, shorter, leather Moto jackets, cardigans and wraps. If your basic uniform is jeans and a tee shirt, you can get a lot of different looks by simply wearing a different jacket every day.
    3. Amp up your accessories. Summer to fall transition is a great time to show off your accessories. Your shoes, belts and handbags will be seen and noticed because you are not all bundled up under an overcoat. Take advantage of this time to wear textured leathers, animal prints, suede, colorful, studded or embellished accessories.

Shop This Fall Transition Outfit High or Low


Max Mara Corona Cable Cashmere Cocoon Cardigan, $1,150

James Perse Casual Tee, $85

GRLFRND Karolina High-Rise Skinny Jeans, $228

Gucci Women’s Princetown Slipper, $950

Gucci Leather Belt, $460

Total High End: $2,873


BP. Open Stitch Cardigan, $49

Madewell Whisper Cotton V Neck Pocket Tee, $19.50

H&M Super Skinny High Ankle Jeans, $19.99

Linea Paolo Annette Loafer Mule, now $65.96

Topshop Leather Belt, $35

Total Low-Priced: $189.45

Do you have a favorite summer to fall transition outfit?


Carol Calacci


You may also like to read more of Carol’s style over 40 posts like How To Style An Endless Summer Outfit High and Low and High Low Styling: How To Make The Transition from Summer To Fall.

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3 thoughts on “How To Style A Fall Transition Outfit High or Low”

  1. I love clothes and thought I pretty much knew what I was doing. But, I LOVE the suggestion of wraps. I don’t have any wraps, but I love the sophisticated look of them. I’m gonna order one! Thanks!


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