Top Hacks for Making Winter Headwear Work for You

Winter is upon us and we are all looking for cold weather fashions – that aren’t ugly Christmas sweaters. Here are our top hints on how to make this season’s top accessory work for you. From the latest runway fashions to fun fashion accessories, head coverings, hats and turbans are perfect for everyday wear, not just bad hair days.

Hats add warmth while adding an extra dash of style. With winter weather already a bit drab and people bundled up in warm coats, headwear and scarves can be the best way to show a little personality. Headwear can also help balance out the bulk of a winter coat to make you look more proportional.

Sadly, many of us are scared to wear hats and other headwear. Do not lose hope. Here are the solutions to the most common hat problems.

Problem: Hat hair

Solution: You can keep your hat on. This is easier than it sounds. Pick headwear that can easily go from indoors to outdoors. The most common problem is people try to wear hats that don’t allow air circulation. This might be fine while you take a quick walk in the cold but once you return indoors, your head is likely to become sweaty and overheated. Pick lighter weight, breathable fabrics and designs that allow air circulation. Think open-weave knits, hats with a higher crown, and lightweight turbans and scarves.

Pick the right materials. Wool is breathable but some people find it itchy, particularly if worn for longer periods of time. Finer weaves of wool and wool blends are less likely to cause a reaction to the wool. A wool hat might simply need a liner in order to be more comfortable.

There are plenty of other fabric options that work well in a variety of temperatures. Fleece, cotton, and silk tend to be quite breathable. Keep in mind that open weave knits, hats with higher crowns, and headwear that is either lightweight or not as form fitting are more likely to remain comfortable indoors. Acrylics are inexpensive but the synthetic material doesn’t allow airflow, however, beanies and other hats are often in an open knit which improves air circulation.

Problem: “I don’t look good in hats.”

Solution: Everyone looks good in headwear. The solution is the find what works for you. There are two common problems:


Make sure your hat is sized appropriately. It should be proportional to your head. Let’s face it, some of us have giant noggins. Other people are petite. Your headwear should fit comfortably, not too loose nor too tight. While individually sized hats are typically available in menswear stores, it isn’t to find women’s hats in a range of sizes. Rather than a one size fits most approach, better hat makers make hats in a range of sizes.

If you have a tougher head to fit and haven’t had any luck locally, check online. To find out your hat size, measure your head (Rambo-style) with the tape measure around the widest part of your forehead. To view a hat sizing chart, click here. For some people, tight headwear can cause headaches or irritate hair. Make sure you have a good fit for your hat and you should be set for the season.


Try plenty of styles of headwear. Various types of hats, caps, beanies, turbans, and scarfs all have their own appeal. People with rounder faces may prefer headwear with height at the crown and a medium to wider brim to balance out their proportions. Oblong faces may want a lower crown and hat with a bit of a brim. Those with square faces will want to soften their silhouette with rounded forms. Heart shaped faces can add balance with a medium-width brim. People with oval faces are lucky as they usually look good in any style of headwear. Asymmetrical styles of headwear can also balance out faces that are round or square.

Problem: “I’d feel self-conscious in a hat or turban.”

Solution: any change in style can be an adjustment. If you don’t feel completely comfortable wearing a hat, ease into it gradually – wear it around the home when no-one else is around and get used to the feel of it, the look of it, and then you won’t feel like you’ve got a foreign object on your head the first time you decide to go out and showcase your new look! Try different types of hats and find a style or two that work well for you.

In the winter, headwear is important to everyone living in colder climates. For some people, it’s more critical. For anyone spending a large amount of time outdoors, who gets chilled easily, or hats for thinning hair or hair loss, headwear can make huge difference in quality of life. Keep experimenting until you find a style, colour, and fabric that feels right. Soon you’ll realise that winter headwear is an important part of your winter fashion style.

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