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How to Transition Your Wardrobe From Fall to Winter With 9 Easy Tips

By
Cassie Bird
Last Modified on November 18, 2025

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Before we know it, we’ll be swapping out our pumpkins for pinecones when fall turns to winter. Autumn always flies by, but this time of year is the perfect opportunity to try to slow down as much as possible and appreciate the change of seasons. Even though winter might bring some unwanted guests (hello, ice), I’ve always loved winter style – almost as much as fall fashion. Cozy sweaters, thick layers, and deep colors all make for enchanting cold-weather looks, and it’s easy enough to ease into winter from fall with a few styling swaps. Master the fall-to-winter transition with these 9 tips!

1. Swap out a trench coat for a wool version

coat | jeans | shoes | belt | sweater | earrings | watch

When I think of fall, I think of a classic trench coat… but what does that mean for winter looks? If you want to make an easy swap to help transition your outfit from autumn to winter, hang up the trench coat and reach for a wool style instead. A wool coat is heavier, warmer, and usually a little more structured than a trench coat, which makes it ideal for colder weather. Although a trench coat is great for in-between days when it starts off cool but warms up later on, it’s not enough when it starts to hail or snow.

A wool coat in a neutral color is the perfect addition to a winter capsule wardrobe. You can style it with nearly any outfit, just like a trench coat, to add a polished touch. Whether you’re dressing casual in a sweatshirt and leggings or going for a more elevated look with dark-wash jeans and a turtleneck, a wool coat adds class and sophistication. If you like the tailored look of a trench coat (thanks to the belted waist), find a similar style in wool to accentuate your natural curves!

2. Exchange loafers for ankle boots

coat | turtleneck | pants | boots | watch | bag | earrings

When you look outside and your neighborhood is covered in a blanket of snow this January, reaching for a pair of flats might not be appealing. What should you reach for instead? A pair of ankle boots. These keep your feet nice and warm (especially if there’s snow on the ground), and pair well with tights if you need an extra layer of warmth on your legs. Boots give your ankles a little extra support, too, which is always a bonus if the ground is slick!

Leather or faux leather varieties of boots are perfect for inclement weather, as they’re easy to wipe clean. Stay away from more delicate fabrics like suede if you’re going to be out walking around in any winter precipitation.

3. Wear your loafers with thick socks

coat | skirt | sweater | socks | shoes | bag

If you do choose to wear loafers, try layering them with thick socks in winter! This helps make your look appear more winter-ready. A pair of cashmere crew socks adds dimension to your outfit, and you can even layer them over sheer tights if you need a little extra warmth.

Although neutral socks are always a safe bet, you can also get creative and go for a colorful pair. This is a favorite style strategy of Parisians, as it adds just the right pop of color in a neutral look. Burgundy, dark green, bright red, or plum would all look great in the winter season!

4. Swap out a silk scarf for a wool one

socks | shoes | jeans | sweater | coat | bag | scarf

Speaking of Parisian style, it’s no secret that French women love accessorizing with a silk neck scarf in the fall. But when the temperature starts to drop, you might see them reaching for a wool or cashmere version instead. It still gives them the same look they’re going for (color, pattern, etc.), but adds a little bit of extra warmth around their neck.

Square-style bandana scarves are a popular option if you don’t like wearing a full-length version. They look great layered over a coat, sweater, or t-shirt, and give you a little boost of coziness without being as heavy as a thick blanket scarf. Plus, you can style and knot them in many of the same ways as a square silk scarf.

5. Reach for thick sweaters instead of thin ones

boots | bag | skirt | sweater | earrings

The colder seasons call for layers, and when fall turns into winter, those layers need to be updated accordingly! Although multiple thin layers are often ideal for fall’s more temperate climate, you might find yourself needing something a little more substantial when winter actually arrives.

Instead of a thin cardigan, opt for a thick cable knit turtleneck when the seasons change. Even if you stick to the rest of a fall outfit formula, this simple swap makes your ensemble look more winter-ready, and it’s extra cozy for the holiday season.

6. Add a pair of sheer tights to your look

jacket | shoes | tights | sweater | skirt | watch | headband

We’ve already touched on this, but a pair of sheer tights goes a long way in helping you to make the fall-to-winter transition in your style. Autumn temperatures are usually warm enough for many of us that we don’t need a pair of tights unless we want them, but winter is a different story, at least in the Midwest. Bare legs aren’t a great idea when it could easily start snowing at any moment!

Fleece-lined tights are always an option if you really need the extra warmth, but if you’re just looking for a little extra coverage, sheer black hose are the perfect addition to your winter looks. An added bonus? These tights make your legs appear longer and slimmer, especially when paired with dark, pointed-toe shoes. Whether you style them with loafers, boots, or heels, sheer tights will make you look more put-together (and weather-appropriate) instantly.

7. Accessorize with leather gloves

pants | heels | bag | gloves | coat | jacket | shirt | earrings

If you live in a cold climate like the Midwest during the wintertime, you know that hydration habits are everything to protect your skin. Winter’s not only an important time to build up your immune system, but also to build up a layer of moisture on your body to prevent dryness!

Although lotion or hand balm will always be non-negotiable in dry, frigid temperatures, gloves will also help protect you against dry skin. And you can use them to your style advantage, too! A pair of gloves will help you make that fall-to-winter transition with your outfits and give you a touch of glamour. The pair above from Quince isn’t only made with sleek leather – they’re lined with super soft cashmere on the inside too, for added comfort.

8. Go for shearling instead of suede

jacket | sweater | jeans | boots | bag | sunglasses

Fall is the time when I reach for suede everything. It’s typically not snowing yet or too rainy, at least in the Midwest, which makes it the perfect time to pull out the more delicate fabric. Suede is a soft, cozier version of smooth leather, which makes it ideal for the transition from warm weather to crisp fall air.

However, when winter does arrive and brings with it the potential of rain or snow, suede pieces aren’t always ideal or warm enough. Instead, try swapping out your suede pieces for shearling. A shearling jacket is much warmer than a suede version in cold weather, and will give you better protection against a sharp bite in the air. Even if you keep the rest of your fall outfit the same, like jeans and a turtleneck, this simple swap makes you look way more fit for a winter outing.

9. Swap out a mini skirt for a maxi one

skirt | boots | bag | sweater | earrings

Although mini skirts can certainly be worn in the wintertime, especially with thick socks and/or tights, you may want to consider reaching for something with a longer length. A maxi skirt is the perfect solution, and is a little more sophisticated and elevated than a mini version, especially in a luxe fabric like silk or satin. It’s also a better fit for a dress code, such as if you’re styling a look for the office this winter.

Another winter-ready piece that can help with the fall-to-winter transition? Try exchanging your solid color sweater in favor of a Fair Isle version for bonus points. This pattern is usually associated with apres ski or the holiday season.

Style Swaps for the Seasonal Shift

When the days start to get shorter, you’re probably going to find yourself reaching for more and more of these wintertime pieces. Just adding a single one to your fall outfit will help prepare you for the holiday season and colder temperatures. These tips aren’t just for colder weather, but for the aesthetic, too! Embrace all that winter entails with these 9 easy style suggestions.

Speaking of the holiday season, are you already excited to give your house a decoration makeover? Pack your fall pieces up in their bin until next year and get ready for fresh greenery, fir candles, velvet ribbons, and festive wreaths. Up Next: Cozy Christmas Decor Ideas With a European Touch

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