7 Winter Style Mistakes That Make You Look Frumpy (And Exactly How to Fix Them After 40)

One of the biggest winter style mistakes that make you look frumpy is wearing the wrong outerwear with your outfit. I see this all the time—someone puts together a beautiful, dressy look and then throws on a casual puffer, which immediately brings the whole outfit down. It just doesn’t work because the formality levels don’t match. Instead, I always make sure my outerwear matches the vibe of what I’m wearing underneath. When I’m wearing a dress, I reach for a faux fur jacket because it instantly elevates the entire look and feels intentional. I love how faux fur adds warmth, polish, and that touch of glamour without trying too hard. I’m wearing a size small in the jacket for a slightly relaxed but still flattering fit.

Another one of those winter style mistakes that make you look frumpy is what I call the marshmallow effect—layering oversized pieces on top of oversized pieces. When everything is big and bulky, you completely lose your shape, and the outfit ends up looking heavy and shapeless. The fix is all about balance. If I’m wearing an oversized jacket, I always keep everything else more fitted so my silhouette still shows. One of my favorite combinations is an oversized bomber with a fitted sweater and wide-leg jeans that are structured through the waist and hips. I love this look because it feels modern, chic, and still very slimming. I size up in the bomber for that oversized look and wear my jeans true to size.

Wearing bulky sweaters untucked is one of the most common winter style mistakes that make you look frumpy, especially when they hit right at the hips or below. This completely hides your waist and adds bulk where you don’t want it. My fix is simple—I choose thinner sweaters that I can fully tuck or at least half-tuck to create definition. Lightweight cashmere is my go-to because it’s warm without being bulky and this one from Quince layers beautifully under jackets. I love how instantly polished the tucked-in sweater looks, even with jeans. I wear a size XS so it’s easy to tuck without extra fabric and I find it fits true to size.

This is one of the worst winter style mistakes that make you look frumpy, and I still see it all the time—showing skin between your ankle boots and your jeans. That little gap may seem harmless, but it completely chops up your leg line and shortens your silhouette. The fix is making sure your jeans fall cleanly over the top of your ankle boots with no skin showing. I love styling these high-waisted wide-leg jeans from  with ankle booties because the hem hits perfectly and instantly elongates the legs. This combination always makes me feel taller and more put together. I wear my jeans true to size and look for ankle boots with a slimmer shaft.

Wearing jackets that are too long is another winter style mistake that makes you look frumpy, even though they may be trendy. While long coats can look cool on others, I’ve found they often overwhelm the frame and hide your waist. Instead, I gravitate toward cropped jackets that hit right below my waistline. This length is incredibly flattering and immediately improves proportions. I especially love this cropped faux fur jacket because it’s incredibly luxe, gives structure to the outfit and keep it feeling modern. I wear a size XS so it hits at just the right spot on my body.

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Another subtle but impactful winter style mistake that makes you look frumpy is wearing round-toe shoes. Round toes tend to visually widen the foot and shorten the leg line, which isn’t doing us any favors. Whenever I can, I choose a pointy-toe boot, heel, or flat instead. Pointy-toe shoes instantly elongate the legs and make the entire outfit look sharper and more polished. I love this pair of mules always notice how much sleeker my outfits look just by making this one small change. I stick with my true shoe size for the best fit.

This is one of the winter style mistakes that make you look frumpy that I see women making all the time – wearing a blazer without styling it! Leaving it unbelted with the collar down and sleeves untouched creates a boxy shape that hides your waist. My fix is a total game-changer: I belt my blazer to define my waist, pop the collar for structure, and push up the sleeves to show a bit of skin. Every time I do this, I look instantly slimmer and more polished. This leather blazer from Quince is one of my most-worn pieces because it works so hard in my wardrobe and always looks fabulous. I wear a size XS and belt it snugly at the waist for a hourglass shape.