Comfortable beanie Our stylists’ favourites for you, plus some tips on how to wear them well

Why you need a comfortable beanie
These days there’s such a fine line between smart and casual, and the beanies here—which don't feature big bobbles or logos—can bridge the gap: They can dress down a tailored overcoat or keep you comfortable in sweats on a Sunday morning. On the arguably more important practical side, they’ll keep you from losing heat from your head.

Stylist, Kasia K.

The best beanie if you think beanies make your face look weird

The fisherman beanie.

1. Thick-knit, so it doesn’t sit too close to your face.

2. Adjustable turn-up you can alter until it looks right.

3. Shorter shape sits higher on your forehead, so it won’t make your face look squished.

The trick to keeping it from messing up your hair

Rather than pushing it onto your head, hold the edge of the beanie to your forehead and bring the back up, then down over the back of your head.

The temperature regulator

Wool is the best beanie material because it naturally absorbs and releases up to 30% of its weight in moisture, which can keep you warm or cool depending on the weather.

The flop factor

“Lots of guys wear beanies back behind the front of their hair, leaving a long flop at the back,” Sophie says. “This slouchy style isn’t sharp—or practical: the hat doesn’t sit tight enough to keep you warm. If you do want to show some hair, I’d roll your hat from the bottom so it hits the same place on your forehead, but without the flop in the back."

The icon

French marine hero Jacques Cousteau (and his descendant Bill Murray in "The Life Aquatic with Steve Zissou") was rarely seen without his jaunty red beanie. A beanie is an easy way to experiment with colour because you're only committed to it when you're outside. And red is a classic way to start.

The longevity

For a beanie that’ll last, look for two things in the product description and photos:

1. Wool, which bends and stretches better than cashmere, cotton and synthetics, thereby lasting longer.

2. The horizontal lines at the cuff that show it’s rib-knit; this tight, thick ribbing holds its shape well.

The matching advice
  • In an unusual twist, not matching is better than matching: a perfectly matched hat, gloves and scarf can look like a cheap packaged set.
  • If you're looking for versatility, go for a navy beanie. It won't show wear, it goes with any other colour hat and gloves, and it looks good with both navy and black coats.
The static solution

If beanies tend to make your hair stand up with static electricity, swipe a dryer sheet on the inside of the beanie before you put it on. The sheet will make the static charge less powerful (and make the beanie smell nice).

The ideal fold

If you want your beanie to look classic, fold the bottom up about two to three inches, or until the top is tight to your head. If you want more of a flop, put the beanie on without folding it, then tuck the fabric near the nape of your neck into itself to create a fold.