Ask Allie: Styling a Summer Dress for Fall and Winter

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.

  • Kati LeTourneau

    I had been thinking about asking this very question!! I have a follow-up though- any tips for when the colors are especially spring/summer? I have some great dresses from LE this summer, but in bright knits (one is a coral square neck and another is a bright green- kind of a blend of lime and kelly green). Would summer colors work as well with the denim + boots? Or do you have other suggestions for bringing in different colors?

  • I was thinking about this yesterday, I saw a woman wearing an apple green knit dress that was very summery in color, but she toned it down with black tights, black boots, and a black belt. The black made it look more mod and less springy. I think coral could work with denim and boots, but the brighter cool tones may be better winterized with black for a more graphic result. 🙂

  • JB#3

    I’m wearing that lipstick right now.

  • I love the idea of a turtleneck underneath! I want to try that!

  • Patti_NotDeadYetStyle

    Oh I cannot *wait* to wear tights and boots – I love this look. It’s 83 degrees here today. xox

  • Lee

    I am completely in love with the brown bag in the first photo — details please!

  • Aimee

    That outfit is amazing. I love all of it.

  • Thing is, I get why lots of people want to do this, but I get bored of most of my clothes from one season and look forward to a change! I do have a few dresses that are more trans-seasonal, but most of them go away in autumn and come back in spring.

  • Lee

    Ah, now I get the scroll bar underneath where I can find the bag at Nordstroms….

  • So sorry for the delay in replying, so you got the link? It’s the Frye “Jenny” Crossbody, and it’s gorgeous in person too!

  • Julie Daum

    I am going to try the first and third looks with a J Jill linen dress that I was inspired to purchase from reading your blog. I fell in love with the dress, both casual and dressy at the same time and super easy to wear and looked edgy. I found a great jean jacket at Target this spring that I haven’t been able to figure out how to style for work that doesn’t look too casual. Thanks!

  • That sounds fantastic! Is it the Ikat dress I featured once?

  • Julie Daum

    I think it was.