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
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
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
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.).
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).