Ask Allie: Styling a Knit Dress for Fall and Winter

Hi Allie, I bought an adorable red-striped dress at J. Crew Factory but need help styling it for fall & winter. I'm thinking a denim jacket will be great with it but I'm not sure about shoe choices. I love boots & already have a camel colored pair, black pair, & dark brown pair. I also have a pair of suede gray Chelsea boots. I don't do heels at all but love flats. I live in Arkansas, so our falls can be chilly & our winters do get cold, so going bare-legged is not a choice for me. Can you help?

It’s so easy to throw a pair of boots and a jacket over a summer dress, but when you truly need to winterize a piece with tights and warmer elements, it does get tough. As you wrote a couple times in your full email and I often say when looking in my closet, “What about tights???” Not everything works with an opaque black pair. Here’s some ways to make your dress, or any summer tee shirt-inspired dress transition into fall and winter.

Add an Accent Color

how to style a tee shirt dress for fall and winter

Shop this Look: Dress | Jacket | Boots | Scarf | Tights

While matching your tights to your footwear is a tried and true way to look cohesive and elongate your leg, an accent colored tight can actually pull an outfit together. You mentioned you have camel tall boots; consider using olive green as an accent color with tights (I love Spanx Tight End Shaping Tights for durability and fit and they have a great olive shade) and pull it together by bringing olive to the top of the outfit with a scarf or necklace.

Make the Dress the Accent

how to style a summer dress for fall and winter

Shop this Look: Dress | Sweater | Boots | Belt | Tights

If you have your topper, tights, and shoes all coordinate, you can use most any color and the dress then becomes the accent. For this look I considered your gray suede Chelsea boots and added a gray v-neck sweater with a longer line, and gray tights (these are Assets by Spanx, they’re reversible adding warmth, opacity, and versatility – I have a pair and like them a lot). I added a leopard haircalf skinny belt to be worn over the sweater and dress to highlight the waist and add interest. This belt could be switched out for a solid contrast color, a different print, or even a scarf.

Keep it Classic with a Leather Jacket

how to style striped knit dress for fall and winter

 Shop this Look: Dress | Jacket | Boots | Scarf | Tights

Leather jackets are great for cool weather, but are also a great alternative for cardigans, denim jackets, and blazers. This look isn’t that drastically different from the first ensemble, but the moto-inspired leather topper gives a bit of a rock & roll vibe. Keep it going with moto-inspired boots, very opaque black tights (check out Hue’s Super Opaque control top tights), and a scarf that has a plaid or “tough” pattern (animal print, skulls, etc.).

how to style j crew factory striped knit dress for fall and winter

Shop this Look: Dress | Jacket | Boots | Scarf | Tights

Want a softer look? Switch out the black for brown or cognac and style with brown tights, riding-inspired boots, and a printed scarf in a classic print (plaid, paisley, floral).


  1. August 15, 2015 / 7:46 pm

    This makes me long for cooler weather we won’t see until October here. The last pairing with a scarf in a classic pattern is particularly scrumptious!
    Leah from

    • August 19, 2015 / 8:11 am

      Yep I too won’t be able to wear such things until late October, but I’ll be rocking tall boots by mid-September, just without the toppers and tights!

  2. crtfly
    August 13, 2015 / 9:53 pm


    You have a brain with a super relational database of clothing and styling info! Push enter and your answers are faster than the fastest computer. It amazes me how you can do this so effortlessly.


    • August 19, 2015 / 8:10 am

      Oh it’s fun. Some people like to do puzzles, I like to style clothing, it’s my puzzle!

  3. Lee4
    August 13, 2015 / 4:49 pm

    Thank you Allie! I’m so excited that you picked my question. Wow!! Ok, let me just say that I love every one of these. That leather jacket in the bottom pic is awesome & may just be on my wish list now.

    You helped me a lot with the tights issue–I was not sure about what color to use & I think I’ll be comfortable going with brown ones & my camel boots. I also intend to find some more gray tights. I’ve got a pair I’m not crazy about (& had totally forgotten I had any at all until I saw this) but I like the gray tights with my boots as another option. I think I’ve been hung up on trying to exactly match my gray boots to my gray tights. Maybe that can’t happen & maybe that’s ok…See, I worry about silly things!

    Thank you for the help today! I’m keeping my dress & will get lots of wear out of it!

    • August 13, 2015 / 4:52 pm

      I don’t think the grays have to matter, you’ll go crazy trying to make it happen! If the sweater, the tights, and the boots are all different but same color story grays (meaning don’t have one be a blueish gray, one more warm, and one be a charcoal heather) it can look really nice!

      • Lee4
        August 13, 2015 / 4:55 pm

        Thanks! That often bogs me down–trying to be so exact. I’m looking forward to styling this dress in multiple ways. You are SO good at this.

  4. Clare
    August 13, 2015 / 11:28 am

    This is really your forte, Allie. Great job. I have this dress, but in blue/white stripes and I’m enthused about your choices.

    • Lisa S
      August 13, 2015 / 12:04 pm

      I concur — I like these features a lot and am actually considering the dress(!) because of at least two of these styling scenarios.

  5. Pam S.
    August 13, 2015 / 11:10 am

    Dang, I could see wearing ALL THE THINGS! I love the idea of using the dress as the accent. I’ve never thought of things that way.

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