By Jason McDowell Creative Director Published Nov 17, 2016 at 1:06 PM

Milwaukee's been pretty pumped about this current mild fall, one that rivals the relatively comfortable temps from last year. But with the snow coming eventually, it just might finally start to look a lot like winter outside – and that means it’s time to look at personal insulation to keep your ears, head and nose warm.

Thanks to the samples we received from Black Diamond and Arc’teryx, we’re showing off the latest styles of beanies and balaclavas with model help from Forward Courier and Bavette La Boucherie.

Check out the features from the beanies below and then watch the video above to see which hats won over our various winter wheeling experts.

The Black Diamond beanies tend to balance style and technicality, while Arc’teryx lean more towards technicality.

Arc’teryx Trino Beanie

Arc’teryx’s Trino Beanie (list price: $29) is a surprising value considering the number of features, which includes Windstopper® side panels, double-layering, ports to hold your sunglasses in place and a layered ponytail slot.

The Trino Beanie from Arc’teryx
Trino Beanie (List price: $29)

Arc’teryx Phase AR Beanie

The Arc’teryx Phase AR Beanie (list price: $35) might initially look similar, but it is much simpler in construction. It’s super light-weight and compactable, and features their Phasic™ textiles, which they say is engineered to pull moisture away from your body and and spread it across the entire garment, allowing it to dry faster.

The Phase AR beanie from Arc’teryx
Phase AR Beanie (List price: $35)

Arc’teryx Rho LTW

Arc’teryx also has the Rho LTW (List price: $35), which is even more similarly styled yet, but this one made with wool, instead of synthetic fibers. I’m always a champion of wool for its natural ability to wick away moisture, its anti-microbial properties and its ability to manage heat and insulate.

The RHO LTW beanie from Arc’teryx
Rho LTW (List price: $35)

All of Arc’teryx’s hats are performance oriented. They are very low profile, which helps reduce wind noise and drag and can also be worn under helmets or even under another hat. They don’t have a super sporty look and thus might look out of place if you’re not actually doing an activity. But layered under a more casual hat, they can still be used fight off those super cold Milwaukee nights.

Black Diamond Matt Beanie

As far as Black Diamond’s offerings, I really like the Matt Beanie (list price: $35). It’s 50% wool, a natural fiber that offers moisture wicking and insulation, and 50% acrylic. Acrylic fibers are something I tend to avoid in a winter hat because it’s basically plastic. Plastic doesn’t handle heat and moisture very well, but blended with natural fibers like wool, it does drive the price of the product down, while maintaining a decent level of insulation. It’s thicker, has a casual fit but can still be pulled down over your ears to still offers performance. It’s a good all-around hat.

Buy the Matt Beanie from Black Diamond
Matt Beanie (List price: $35)

Black Diamond Karina Beanie

The Karina Beanie (list price: $35) is a similar hat, but with higher percentage of wool (and alpaca!) and a cabled styling.

Buy the Karina Beanie from Black Diamond
The Karina Beanie (List price: $35)

Black Diamond Niclas Beanie

The Niclas Beanie is 100% acrylic is the value buy that gives you that Zissou-charm (list price: $25).

Buy the Niclas Beanie from Black Diamond
The Niclas Beanie. (List price: $25)

All three of the Black Diamond hats are more outwardly fashion-forward and not specifically designed for layering. But as the video above proves, while maybe not ideal, they can be still used in performance-oriented situations.

Black Diamond CoEfficient Balaclava

For full-faced ultra protection, it’d be hard to go wrong with the CoEfficient Balaclava (list price: $35). It’s a thick balaclava made with Polartec® Power Dry® fleece that traps heat inside the furs and dimples. The design is very comfortable when the mouth-protector is pulled down and out of the way. The problem with more standard balaclavas is they tend get uncomfortable or the elastic gets stretched out in a way that the double-piece construction mitegates against. It also offers double-insulation over your ears, and still allows sound penetration.

CoEfficient Balaclava from Black Diamond
The CoEfficient Balaclava (List price: $35)

The bottom line

Choosing a hat may seem like a simple choice. All you gotta do is pick the color your friends like on you and go, right? But in the end, the climate will have the last word. Make sure you’re choosing something that can handle the scrutiny of both.

Jason McDowell Creative Director

Jason McDowell grew up in central Iowa and moved to Milwaukee in 2000 to attend the Milwaukee Institute of Art and Design.

In 2006 he began working with OnMilwaukee as an advertising designer, but has since taken on a variety of rolls as the Creative Director, tackling all kinds of design problems, from digital to print, advertising to branding, icons to programming.

In 2016 he picked up the 414 Digital Star of the Year award.

Most other times he can be found racing bicycles, playing board games, or petting dogs.