7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

August 24, 2022

7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Words & Style

by Stacey Jones

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7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Note: Purchasing via a link in this article may earn me a portion of the sale, which helps fund my editorial mission.

Note: Purchasing via a link in this article may earn me a portion of the sale, which helps fund my editorial mission.

Keep wearing those summer pieces well into fall with these 7 looks... 

Come this time of year my private personal style clients start reaching out me to ask about summer to fall transitional outfits.

It can be a challenge to put together looks that work with the changing of the seasons. The good news is, while you'll want to start pulling out some of your fall clothing you can pair it with summer dresses and skirts.

I recently went on a mission to find pieces at J.Crew that are perfect to wear now and later. Dare I say, Mission: ACCOMPLISHED.

You can see the seven summer to fall transition outfits I styled below using to key pieces, a sundress and maxi skirt...

Shop the Looks

Tap the images to get more details on each piece shared in this post...

Keep scrolling to see pics of the looks and to get more details on the key piece from each one...

7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Me: 5'3", size 4 | Item size: S | Fit: True to size 

Collared Cotton Beach Sweater by J.Crew

7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Me: 5'3", size 4 | Item size: S | Fit: True to size 

V-Neck Cotton-Cashmere Cardigan by J.Crew

7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Me: 5'3", size 4 | Item size: S | Fit: True to size 

Cashmere Patch-Pocket Cardigan by J.Crew

7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Me: 5'3", size 4 | Item size: S | Fit: True to size 

Cashmere Classic-Fit Crewneck Sweater by J.Crew

We all know you can add a blazer or denim jacket to our outfit to beat the chill and look seasonally appropriate.

What about putting a shirt or sweater over your dress like I did with this sundress? This is a quick, easy, and stylish way to get more wear out of your summer dresses as the seasons change. 

Consider adding a belt for another element of style and to keep your shape.

Me: 5'3", size 4 | Item size: 4 | Fit: True to size 

Say hello to your new favorite sundress. Featuring super-comfy smocking and a flattering A-line skirt, it's an easy go-to for special occasions, picnics or just walking around town.

Smocked-Waist Dress by J.Crew


7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Me: 5'3", size 4 | Item size: S | Fit: True to size 

Cashmere Classic-Fit Crewneck Sweater by J.Crew

7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Me: 5'3", size 4 | Item size: S | Fit: True to size 

Cashmere Classic-Fit Crewneck Sweater by J.Crew

7 Stylist Approved Summer to Fall Transition Outfits from J.Crew

Me: 5'3", size 4 | Item size: S | Fit: True to size 

Cashmere Patch-Pocket Cardigan by J.Crew

I appreciate summer collections in dark florals and prints because they’re easy to wear all year. This maxi skirt, for instance, will look great with your chocolates, your rusts and your taupe or ivory booties.

I recommend pulling a lighter color out of the palette, like I did with the pink sweater in the pic above. “Barbiecore" is a big trend right now and will continue into the fall and winter. Pastels all year long are acceptable and even celebrated. Just make sure your fabrics and styles are cold-weather appropriate. No open-toe baby blue sandals, etc.

One more thing to consider… if you are wearing a heavyweight sweater your belt needs to be wider to bring everything in smoothly. The lighter the sweater, the skinnier the belt can be.

Me: 5'3", size 4 | Item size: S | Fit: True to size 

A flowy, comfy tiered style skirt made with organic cotton that is grown without chemical fertilizers and pesticides from non-genetically modified seeds.

Tiered Pull-On Maxi Skirt by J.Crew

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