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How to Dress for a Warm Weather Winter

How to Dress for a Warm Weather Winter

It’s mid-winter and the forecast calls for 80 degrees tomorrow. Never mind that it was in the 30s all last week! And, insult to injury, you just packed away your summer clothes. Sound familiar? We get it! We understand how frustrating it can be to figure out what to wear when temperatures are not cooperating with the season. But take heart, with some simple planning and the right pieces of clothing and accessories, putting together your ready-for-anything winter weather wardrobe is easily achievable.

In this post we'll go through our top tips on exactly how to dress for warm weather winter so that no matter what temperature swings come your way, you'll feel comfortable throughout the day and as stylish as ever.

If you do nothing else, layer!

Layering is the key to staying comfortable and looking great when the weather can’t make up its mind. Layering is also an art. And the greater Mother Nature’s temperature fluctuations are in your area, the more agile the artist needs to be. It’s all about how to layer. These lookingGLASS tips will have you mastering winter layering like a pro! Whether you're heading out for a hike in nature or headed into the office for an important meeting on those blustery-to-warm-and-back-again-within-a-twelve-hour-period days, here are some tips that will help you create the perfect warm weather winter wardrobe layers. 

It can definitely be tricky trying to figure out how to stay warm during colder morning hours without over-dressing or feeling uncomfortably warm under too many layers of clothes as the temperatures heat up. Think seasonal fabrics and accessories.

Experienced skiers know that layering effectively can make the difference in a great day on the slopes or one filled with the distraction of wondering how long it will take to get to the ski lodge for that cup of piping hot cocoa. Skiers are great layerers. But then again, you probably aren’t going to find a lot of great office attire in Gor-Tex! So, what’s the secret for being weather-appropriate and looking great, wherever your day takes you? The right layers!

How to layer

Generally, you can think in terms of two or three layers, depending on how cold and how warm the day is going to be. If it’s going to be fairly warm, but the morning is chilly, you might get away with a short sleeve blouse or top under a warm, long sleeve cable-knit sweater. Vests are super versatile and can be just the right extra layer to do the trick. A cropped denim jacket with the sleeves rolled up or a lightweight flannel shirt over a tank dress also work well to cover this kind of weather. The key is that you can quickly and easily shed your outer layer as things warm up. You can vary the options for keeping your upper body comfortable by adding a camisole layer and varying the sleeve length of your top or blouse. With today’s popularity of the layered tops look, the stylish options are endless.

Outfit for winter in warmer weather

Trousers and Skirts

Even though winter days may turn unseasonably warm, that doesn’t mean you should break out your floral cotton sundress and your flip flops. To everything there is a season, and every season has its own signature. Each season has a character of its own, a feel of its own. The smell and freshness of the air are different. The patterns and appearance of the deer and the birds are different. The light patterns of day and night are different. Even the position of the sunrise and the sunset are different. Mother Nature has her own rhythms, patterns and vibes. And there’s just something about feeling in sync with Mother Nature.

At least in the continental U.S., the weather usually bears the signature of the season, but not always. Therein lies our challenge. How do we dress mid-winter for a day that’s warm enough to go swimming and still keep a sense of the season in our look? For one thing, fabric. Fabrics like wool, tweed, flannel, velvet, corduroy and fleece just put out a vibe of seasonally in-sync style! Even if you just include the winter fabric element in an accessory, like a sherpa crossbody bag.

Build your warm weather winter outfit around a pair of trousers, shorts or skirt out of a lighter weight winter fabric, or a heavier weight cotton. Wear darker shades and colors and patterns that have a winter feel. Paired with a cool tank top or short sleeve blouse, you’ll be in perfect seasonal style.

The Hat Trick

The secret to the hat trick is having just the right accessories in your hat to allow you to presto-change-o your outfit to suit the ambient temperature by quickly and easily putting on or removing a few strategic accessories.

Hats, scarves and even gloves can take the nip out of those chili mornings, while being easy to whip off as soon as it gets warmer or you step into your cozy office. The ever-stylish muffler of medium to light weight or even small scarves worn around the neck can make a surprising difference in how warm you feel, and are easily removed when the temps tilt to warm. And don’t forget that vests are also a great transitional weather choice. With so many fashionable styles and fabric options available, it’s a great idea to have one or two versatile vests in your closet.

Seasonal Shoes

Wearing the correct shoes will go a long way toward giving your outfit that seasonally-appropriate look. You can wear the cutest sweater vest with wool hat, but if you’re walking around town in flip flops or sandals, your winter outfit is a bust. Leave your flip flops at home and instead opt for light weight sneakers, closed-toe slides, mules or loafers.

The takeaways

  • Plan Ahead. Do plan ahead. Like a good boy scout, be prepared. Planning ahead gets you half way to your goal of looking put together and stylish, plus feeling comfortable throughout the day, regardless of unseasonal swings in the weather. 
  • Check the Weather Forecast. You’ve no doubt noticed that weather patterns lately seem a little wonkier than usual. Don’t be taken by surprise. Make yourself proud and familiarize yourself with your region’s weather patterns and check the next day’s forecast the night before. You’ll be glad you did when you’re running late, the kids won’t cooperate, you’ve laid out your beautiful new cashmere turtleneck—it was 30 degrees yesterday—and, turns out, the high today is in the upper 70s. Remember to factor in things like windchill and humidity. And days where the temp climbs to the low 70s but only stays that high for an hour will feel very different from a day where the thermometer stays in the low 70s for several hours.
  • Think Range. With more intense weather events and temperatures fluctuating even more than usual, another good tip is to think of the temperature ranges—30s-40s, 40s-50s, 60s-70s, and so on. And think of what you usually wear to feel comfortable in those temperature ranges. Your smartphone weather app will graph the day’s temperature and time of day, so you’ll know when and for how long to expect the highs and lows and can dress accordingly using the tips and tricks in this blog post.
  • Buy Right. If you’re buying new items of clothing or accessories, consider whether you have pieces that would be good in unseasonal weather. 
  • Layer and Pair. Create different layers with pieces that can be easily put on or removed as the temperature varies. Pair something heavy with something light.
  • Things to Avoid. Avoid florals, neons, tropical prints Avoid flip flops or a strappy summer sandals that scream July. Leave your espadrilles and wedges at home.

Do you need help putting your outfit together?

Whether you're a busy mom on the go, in need of versatile outfits that can handle everything from playdates to meetings, or a woman who wants to express her one-of-a-kind style with confidence, our personal styling services are designed just for you. 

Contact us here to get started with a personal stylist! 

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