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How to Layer Stylishly for Cooler Weather: Women’s Classic Clothing Tips

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Here at Jenny Boston, we never let anything interfere with our fashion sense. Sure, the weather outside may be frightful, but we’re still pulling out all the stops with our ensembles. In fact, winter is one of our favorite seasons — after all, extra layers just means more looks to play with! Here’s how we create lovely layered outfits during the colder months.

Start Simple

Many classic women’s clothing pieces are designed for layering in the winter months. Items like oversized sweaters, long coats, and quilted tights and leggings are designed to keep you at the height of fashion (and prevent you from freezing to death). However, wearing these pieces properly does take a bit of practice.

Instead of jumping straight for the fleece-lined long johns, start with some light base layer clothing, such as classic long sleeve shirts. This will give you a little extra fabric to keep the cold air off your skin, but it won’t weigh you down with too much fabric.

Balance Out the Bulk

When you learn how to layer clothing, you have to quickly get a sense of balance. If you wear too much up top, you’ll look like Ralphie’s brother from A Christmas Story (“I can’t put my arms down!”).

Experiment with different looks until you find the perfect mix of comfort, warmth, and style. For example, you can wear thick, wooly socks (extra points if they have a fun pattern), tights or leggings, and a knee- or mid-length skirt to keep your bottom half cozy and mobile, while a simple long-sleeved tee/chunky sweater combo keeps you nice and toasty up top!

And remember: this season isn’t all about snow boots and puffy coats. These pieces are great for hitting the slopes on a holiday weekend, but not necessarily for going to the office! Look at the classic women’s clothing you already have in your closet and see which items can do double-duty as cold-weather wear.

Stay Dry with the Right Shoes

There’s nothing worse than heading out the door in the morning and stepping in a pile of wet slush — particularly if you’re not wearing protective shoes. During the winter, you need footwear that will keep your toes happy and dry all day long. If you’re stepping out in your standard pumps, flats, or sneakers, you’re dressing for the season.

A pair of sturdy leather boots are best for the winter (faux leather is ok too). Riding boots or ankle booties are great, but we recommend the over-the-knee style. These keep your feet and lower legs dry, add an extra buffer between your legs and the winter air, and they are incredibly cute with just about all women’s classic clothing!

But whatever boot style you sport, it is always important to layer up first. Start with base layer clothing like an insulating pair of socks — or, if you want a lighter material, try a pair of tights.

Accessorize Smartly

The right winter accessories can help you create a polished look that really wows, and some might even help you stay healthy all season long.

The plaid scarf is a staple of women’s classic clothing in the winter, and it’s one that we always grab before heading out the door. Your scarf is the one part of your outfit where bulk can be a benefit. Some research even suggests that a nice, thick scarf or wrap can help protect you from the common cold!

Of course, your accessories aren't just about temperature control. The right finishing touches can give any look new life — even in the dead of winter. For example, instead of wearing the old knit beanie, cover your noggin with a wide-brimmed hat like a fedora. This will give your outfit some fashionable flair while also keeping the snow off your head!

Don’t Forget Your Coat

We’re not just talking about your standard windbreaker in hot magenta anymore. These days, you’re a sophisticated, fashionable woman, and you should have elegant outerwear to match your women’s classic clothing. We suggest that you invest in a striking statement coat you can wear for many winters to come.

Rather than treating your coat as a separate clothing piece, consider it another layer of your look. Whether you wear a long wool trench, a structured suit jacket, or a brightly-colored raincoat, make sure it is cohesive with the other items you have on. This will give you a polished, complete look, and leave everyone who sees you with their jaws on the floor.

The key to winter fashion is learning how to layer clothing. But as you can see, proper layering isn’t as hard as you think! With a few simple rules and the right base layer clothing, you’ll be warm, dry, and oh-so-cozy — but best of all, you can look like a true fashionista from fall until the first signs of spring.


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