Ask Allie: Styling a Summer Dress for Fall and Winter

Fashion Advice How to Wear Fashion Trends

Can you possibly help style Loft's Lou & Grey Ottoman Stripe Dress in Intense Burgundy? Love the dress but am struggling with what to wear in the cooler months of Autumn. Thanks SO much!

What a cute dress (also available in two other color combinations), how did I miss this during my many trips to LOFT? It is a great transitional dress, and quite a versatile color combination. Here’s a few ideas to wear the Lou & Grey Ottoman Stripe Dress as the weather gets colder:

How to Style a Summer Dress for Fall and Winter featuring the Lou & Grey Ottoman Stripe Dress from @LOFT


The easiest way to transition a short-sleeved dress for fall is with a denim jacket and boots. This year, denim jackets are prevalent in stores, so you can find a fit and wash that works for you. With the color of this dress, you can do anything from distressed light denim to a crisp dark resin finish. As for boots, any height will do, go with what looks most flattering for your body type. I chose a shorter boot to balance the volume of the dress, but if the dress is shorter on you or not as full a knee-high style would also work. Here, color is also up to you; brown, gray, camel, or black would work, but if you choose black be sure it’s a more casual boot (not super shiny, lower heel, rounder or chunkier toe) to complement the casual style of the dress. To add some warmth, sweater or cable tights in a color similar to the shoe (gray with gray, brown with brown or camel, gray or black with black) would fit the casual feel nicely.

How to Style a Summer Dress for Fall and Winter featuring the Lou & Grey Ottoman Stripe Dress from @LOFT


Who’s to say your layers have to be over the dress? A thin fitted turtleneck is a great way to extend your summer dresses into the cooler months. For this look I kept the under layers consistent with opaque non-shiny tights to match the turtleneck. A pair of booties adds some heft to the bottom of your figure to balance the casual style and volume of the dress.

How to Style a Summer Dress for Fall and Winter featuring the Lou & Grey Ottoman Stripe Dress from @LOFT


A long cardigan or sweater coat would work really well with a dress of this type. To make it dressier enough for a business casual office, I decided to stick with all black. A sleeker bootie with a heel will dress up the look without looking out of place. A smoky eye would add an artistic edge to the look; a pendant necklace would be a nice way to add interest and a bit of your own personal style.

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