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Winter Style: Mixing a Silk Skirt with an Oversized Sweater

Happy Thursday, Ladies! You may have noticed that we have a brand new website! Yesterday, many of you experienced a glitch in our system where you were asked to pay to see blog content – this was a technical error that has been fixed. Style at a Certain Age will always be available for free. We are, however, presenting a new subscription service for ad-free blog posts and exclusive content for those of you who want to experience Style at a Certain Age without any ads. This is a huge milestone and an exciting time for all of us, and though we have had some technical issues, we are working hard to resolve them. So please bear with us as we work through the tech to give you the best experience on Style at a Certain Age. Now, on with Winter Style…

Today I’m bringing you a winter style combination that you might not expect, but I promise, it works beautifully: a silk skirt paired with an oversized sweater. Yes, silk and sweater-weather can definitely coexist, and I’m here to show you how to make it work without sacrificing warmth or style.

The Charm of Silk for Winter Style

First of all, let’s talk about why silk is such an underrated fabric when it comes to winter style. While it’s often associated with delicate summer outfits or fancy evenings out, silk is actually a wonderful insulator. It holds warmth really well, and because it’s breathable, it helps regulate your body temperature. So, if you’re layering it up right, a silk skirt can actually be surprisingly cozy for winter.

Shop Silk for Winter Style

An Oversized Sweater for Winter Style

Now, let’s move on to the oversized sweater. It’s comfy, it’s cozy, and most importantly, it’s chic. When the temperatures drop, we often find ourselves reaching for big knits and chunky layers—but here’s the thing: it’s easy to get lost in those oversized sweaters if you don’t balance it out with something more structured or fitted. Enter the silk skirt.

The beauty of pairing a luxurious silk skirt with a cozy oversized sweater is that it’s the perfect juxtaposition for winter style. You get the warmth and laid-back vibe of the sweater, but the silk skirt adds a touch of elegance and femininity that elevates the entire look. I am wearing a regular size XS in both the sweater and skirt.

100% Washable Silk Skirt | Relaxed V-Neck Sweater | Sheer Tights | Patent Leather Block Heels | Loulou Bag | Loulou Bag Similar | Similar Layering Necklace

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How to Style It

Now, let’s get into the fun part—how to style this look!

Choose the Right Silk Skirt

Longer skirts keep your legs covered and warmer so go for a knee-length or midi skirt. Look for skirts in jewel tones or deep hues like emerald, burgundy, or navy—these colors feel so cozy and luxe for the season. If you’re feeling adventurous, metallic skirts or rich patterns can bring a little festive flair to your winter style.

Go For an Oversized Knit

The key to pulling off this look is choosing the right oversized sweater. You want it to be relaxed, but not so oversized that you look swallowed up by fabric. Think soft, oversized turtlenecks, chunky cable knits, or even a cozy cardigan draped over your shoulders. If the sweater is a little too long or boxy, tuck the front in slightly at your waist to create shape, or go with a cropped sweater. This will keep the outfit balanced and prevent it from feeling too frumpy.

Layer Up with Outerwear

If it’s really chilly where you are, layering your outfit with a warm coat or jacket is a must. A classic wool coat or a tailored trench will keep you toasty while still maintaining a sophisticated vibe. For an edgier twist, a leather jacket works beautifully over this look, especially if you want to give it a bit of contrast between soft and structured elements.

Footwear That Complements the Look

Footwear is where you can really tie the whole outfit together. Since a silk skirt has a bit of sheen, pairing it with boots helps ground the look. I love knee-high leather boots, especially in a neutral shade like black, brown, or even a bold tan to complement the warmth of the sweater. If you’re feeling playful, opt for combat boots for a more street-style feel. I wanted to keep this look more romantic, so I went with patent leather block heel pumps with a feminine ankle strap.

Accessorize

Add accessories that feel warm and cozy. Think chunky scarves, textured berets, or soft knit beanies. A sleek leather bag or a chic tote can keep your essentials close by while adding another layer of polish to your winter style.

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Why This Look Works

The combination of silk and oversized sweaters is everything I love about winter dressing: it’s comfortable, layered, and elevated in a way that feels effortless. The silk skirt adds a luxurious touch, while the oversized sweater keeps it grounded and cozy. This mix of textures and proportions not only keeps you warm, but it also keeps you stylish without even trying too hard. It’s the perfect way to channel winter chic, whether meeting friends for coffee or heading out for a date night dinner.

So there you have it! A winter look that’s as practical as it is stylish, and definitely one you can wear all season long. Give it a try next time you’re looking for something a little more playful and unexpected in your winter wardrobe! For more ways to create winter style with silk, check out New Year, Classic Style.

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  1. Cynthia Fisher

    I LOVE this look

    1. Thank you so much, Cynthia! xo Kelly

  2. Sherry Ulrich

    Love the silk skirt with sweater. 2 , Sundays past I wore my navy silk skirt with a light blue sweater with sequins to church. It was pretty chilly outside, so I wore boots with it. Really like this look too. Like your new set up for the comment section. More user friendly.

    1. Your church outfit sounds beautiful, Sherry. And thank you so much for your feedback on the new site! Thank you for being here, xo Kelly

  3. Carolina Girl

    Simply adorable, from head to toe!

    1. Thank you, Carolina Girl! So happy you’re here! xo Kelly

      1. MaryLynne

        Silk and wool are a great cold weather combination. I have silk long underwear from Wintersilks which, unfortunately, are no longer in business. A silk camisole under that sweater will keep you toasty. If you want warmth without bulk, say for traveling, silk under cashmere is perfect. With the wind chill at 15 degrees today, I’m wearing my silk and wool. love the new look on the blog!

        1. You are so right, MaryLynne! Silk worn under a knit piece is a fantastic combination for cold weather. Natural fabrics cannot be beat when it comes to insulation and keeping cool in hot temps. Thanks so much for your feedback on the new site! xo Kelly

  4. Dottie Kinnaman

    Love this. I have to go to a funeral and just this morning, I was thinking of wearing my black silk skirt with a gray cashmere sweater and either pumps or ankle boots. So guessing I’m on track with the style.

    1. Hello Dottie, it’s a beautiful ensemble, classic and tasteful. Thank you for stopping by, xo Kelly

Navy Coat winter outfit

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