22 Staple Pieces To Transform a Summer Wardrobe into a Winter One

22 Staple Pieces To Transform a Summer Wardrobe into a Winter One
Image: Old Navy

old navy blanket scarf
Old Navy

The summer of 2018 is almost over. It feels so weird to say -- I swear it was only yesterday that June started. Looking at my calendar, September is right around the corner, which means some big changes are on the way. Along with the beautiful colors of autumn in the trees, and later on the ground as the leaves fall, comes the change in weather. With fall as its vehicle, winter creeps upon us ever so slightly after the warmth of summer dissipates. Which of course means that our wardrobes need to change to accommodate the weather -- but transitioning through seasonal wardrobes can get expensive. 

Although the shorter, chillier, and darker days can be sort of depressing, one of my favorite things about the colder weather is the fashion. The darker, moodier tones are back in style -- I'm talking burgundy, teals, deep purples and browns -- in apparel and in makeup. We can finally pull back out all the accessories, and have fun with layering and wrapping ourselves.  

With the right staples, we don't even have to put our summer clothing away. We can make fresh new fall looks by layering our favorite lightweight dresses or thin tops over and under these items. In the end, this saves us much more money than having to buy a whole new wardrobe for fall/winter. It's also a space saver, because we won't have to find storage space for an entire seasonal wardrobe. Let's look at a few autumn essentials that we can use to bring some of our warm weather faves along for the ride through winter. 

  •  Beanie


    Hats are some of my favorite accessories that the chilly weather forces us to wear. If I could, I'd wear beanies all year round, but in the summer heat I'd probably pass out. This chunky-knit beanie comes in a bunch of colors, and does wonders for a wardrobe aesthetically and functionally as it gets colder. 

    Unisex Knit Slouchy Hat Beanie ($33, Etsy/ifonkaa)

  • Leather Beret


    Everyone has probably owned a wool beret at least once in their lives. I've always loved the classy, Parisian look a beret gave me, while still keeping my head warm, but the wool ones with no lining pulled my hair out, which was no bueno. This leather version can solve the hair issue, as well as add a little rock 'n' roll element to a classic look.

    Faux Leather Beret ($39, Urban Outfitters)

  • Jumper/Overall Dress


    An upgraded version of the jumpers we used to wear as a school uniform back in the day, an overall dress is a great layer to add to a winter wardrobe. This piece would look great with a band tee layered over a long-sleeved one, or a under a thick bomber jacket, paired with some cool tights and boots. 

    Plaid Overall Dress ($50, Hot Topic)

  • Denim Overalls


    Overalls are a great way to hide a million layers of clothing while still looking cool. What once was something we only saw farmers or construction workers wearing has now become a widely accepted trend. 

    ASOS Design Tall Denim Overall in Stonewash Blue ($67, ASOS)

  • Turtleneck Top


    My daughter hates it when I put her in a turtleneck. I remember hating turtlenecks when I was a child. Now, I love them, and the styling potential they give me. A great staple piece, a turtleneck protects the neck from sudden chilly winds, looks great paired with any types of bottoms, and also works under a dress or top. 

    Striped Turtleneck Top ($10, Forever 21)

  • Fuzzy Scarf


    Fuzzy scarfs like this one instantly protect our faces and necks from freezing. Made out of material that resembles fleece, we'll feel like we're being hugged by the warmest, coziest little lamb. 

    Oversized Teddy Scarf ($29, Urban Outfitters)

  • Blanket Scarf


    As a lover of all things tartan, blanket scarves are right up my alley. They come in a myriad of shades of plaids are perfect for winter outfits.

    Flannel Blanket Scarf ($23, Old Navy)

  • Long Cardigan or Duster


    A long-line cardigan or duster is also a great addition to a fall/winter wardrobe. The perfect topper for items that might not be warm enough, it covers the body from head to toe. 

    Cardigan with Metallic Thread ($70, Zara)

  • Faux Fur Vest


    With the prevalence of faux fur these days, anyone can get the look of wealth with a vest like this. But more than looking rich and divine, these pieces provide some serious heat with their high necks and pockets. 

    Tawny Fox Faux Fur Hooked Vest ($169, Donna Salyers Fabulous Furs)

  • Down Vest


    Don't like the feel of fur? A padded vest provides a great alternative. Where the furry vest is normally worn as outerwear only, a padded vest can be the last piece one throws on before stepping out, or can be worn as one of a many layers under a coat. 

    Women's Ultra Light Down Vest ($50, Uniqlo)

  • Faux Leather Moto Jacket


    Faux leather jackets, of all types are great for fall because they retain some serious heat. I have many memories of wearing a moto jacket, trying to be cool, and overheating because it was still warm outside. But when the weather is just right, or too chilly to not wear a jacket, a moto jacket can be our best friend. 

    Faux Leather Moto Jacket ($100, New York & Company)

  • Cropped Cardigan


    The near polar opposite of its cousin, the duster, a cropped cardigan is great for a day where its about 60 degrees -- just a tad bit chilly to wear a sleeveless dress, but too warm for anything thick or bulky. Cropped cardigans are great additions to almost any outfit, and do wonders for the waistline.

    Collectif Pinup Paradise Cropped Cardigan ($55, ModCloth)

  • Chunky Oversized Cardigan


    Yes -- I know -- another cardigan! That’s because there are just so many different styles. A chunky knit sweater is one of my favorite styles because they remind me of wearing a quilt. These really are great to pair with summer clothes during fall weather. I love wearing them with like an oversized dress and leggings.

    Open Knit Cardigan ($54, Venus)

  • Pullover Sweater

    Ombre blue and white sweater

    Its all in the name: The ease of styling a pullover sweater is as simple as just pulling it on. Pull it on over a dress, pull it on over a tank or even as a roomy standalone top. 

    Textured Ombre Pullover Sweater ($98, Gap)

  • Classic Denim Jacket

    denim jacket

    The jean jacket is truly an all-American wardrobe staple, a classic if you will. Denim always adds a fresh, outdoorsy feel to any ensemble, and the right kind can block out all cold air. 

    Denim Jacket ($40, H&M)

  • Cape


    A multi-use cape like this really has all our bases covered. On an especially windy day, we can use it as an oversized scarf. On a day when there's just a tiny chill in the air, we can wrap ourselves in it, like a shawl or poncho. 

    ASOS Design Plain Cape in gray ($29, ASOS)

  • Colorful Tights

    Tights are the ultimate practical accessories. When winter’s over, I always struggle with parting ways with them because I just love what tights do to an outfit. A simple black dress becomes a Fashion Police-worthy ensemble with printed or lace tights and a pair of boots. I love how tights also permit us to wear colors we would never wear, in moderation, as they peek through the space between the hem of our skirt or shorts and our shoes or between the holes in a distressed jean.
  • Leggings

    Grey leggings

    Arguably one of the most comfortable garments known to our generation, leggings are the go-to running errands garment. But their versatility extends beyond just casual wear. With so many versions of leggings on the market -- corduroy leggings, leather leggings, polyester leggings, cotton leggings -- their range of uses can be extended. They work in winter to replace tights and thermal underwear to keep a person warm or serve as pants under a chunky knit sweater. In fall, they pair with a blouse or a sweater dress and boots. 

    Herringbone Leggings ($30, Gap)

  • Boot Socks


    I honestly never knew there was an actual sock called a "boot sock" before researching for this article, but I've seen and have wanted to wear this look many times. Boots are a fall and winter essential, we know that. But boot socks, whether worn with bare legs, over jeans, or over tights, add a cute embellishment to any cool weather look. 

    The Original Button Boot Socks with Lace Trim by Modern Boho ($13, Amazon)

  • Insulated Boots


    Fleece-lined boots are one of the greatest inventions ever. Originating in New Zealand and Australia in the 2000s, a trend was ignited with the creation of the Ugg boots with their sheepskin interiors. After that, they started popping up everywhere, and became acceptable with almost any type of outfit. When I'm trying to achieve the ultimate warmth, I love to wear boots like these with a pair of leggings under a dress or some sweats.

     UGG Bailey Bow II Boot ($205, Zappos)

  • Combat Boots

    Black Dr. Marten, combat boot, with high top

    Contrary to their name, combat boots don't have to be worn only with army fatigues or cargo pants. Doc Martens, or any other similar style boot, are a great way to add a little bit of a casual but hip vibe to a more classic piece, namely jeans and a tee, or even a dress/cardigan combination. 

    Dr. Martens Coraline Combat Boot ($75, DSW)

  • Thermal Underwear


    I think we all have fond memories of those matching thermal underwear sets we'd wear under our clothes or as pajamas during winter. They were so ugly, right? Thermal underwear works well  for layering in the winter, and now there are affordable sets, like these by CuddlDuds that come in softer and more attractive materials, as well as nice patterns. No longer do we have to worry about wearing a floor-length skirt and turtleneck with our "Long Johns."

    Fleecewear with Stretch Legging ($28, CuddlDuds)

    Softwear with Stretch Long Sleeve V-Neck ($32, CuddlDuds)

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