Sexy-Chic Shoulder Length Hairstyles for Beanie Season

We've literally got you covered.

We’re enjoying this beautiful mild weather as much as the next gal—bye, bye, humidity!—but we do admit it comes with its share of drawbacks. Windy days and chillier nights now have us reaching for the cover-ups and are literally putting a kink in our looks. Particularly, that summer lob: Too short for a proper updo and too long to completely tuck away, it seems like the shoulder length hairstyles that were so hot this past season have finally met their match: the fall hat.

No shade on your trusty, hardworking head accessories though—they’ve seen you through the worst of it, we’re sure—but we can definitely do without the hat head and staticky flyaways. Read on to see some of the best, most sophisticated shoulder length hairstyles you can rock even while bundled up.

1. Bright Blonde Locks

shoulder length hairstyles blonde
A bright blonde stands out even while covered up.

Vibrant, blonde hair doesn’t need an introduction, and certainly doesn’t need much dressing up to stand out. Even while snuggled under a skull cap, the mid-lengths and ends are vibrant enough to make a statement. A medium-length cut that dusts the shoulders and collarbones is ideal for bleached hair, too as it cuts off damaged ends and keeps the hair healthy-looking. Bonus points for some texture too.

2. Layered Shoulder Length Hairstyles

shoulder length hairstyles side bangs
Side-swept bangs resist cowlicks longer. Photo credit: Suzanne Cohen Photography

Jonesing for bangs but afraid of the dreaded helmet head? Opt for a fuller fringe or loose side layers instead. Thicker hair means more density on the hairline and crown, which means a smaller risk of your beanie or hat carving in a dent on your mid-lengths. It’s also the fringe to go for if static and cowlicks are a problem, as strands cut in this manner usually lay down neater from the crown and keep their integrity when swept to the side, as above. As far as length goes, keep your bangs at the golden mean—we like ’em around three millimeters past the brows—for a softer, more graceful gaze (and for a bit of wiggle room when peeking under your brim). Otherwise, keep them at cheekbone level for a layered effect.

3. Pigtail Braids

shoulder length hairstyles pigtail braids
Go to market or stay home: Trendy pigtail braids quickly inject some style into any casual look. Photo credit: Dvora

Pigtails worn under a baseball cap or beanie lose any juvenile associations when rendered in a casual, haphazard (read: not campy) braid. It’s this almost-an-afterthought feel that gives the look its street cred. For a more directional look, go for plaits that are pancaked or tugged outwards: This imparts a more textured, overall rumpled aesthetic that goes perfectly with your cozy fall headgear.

4. Loose Wavy Shoulder Length Hairstyles

shoulder length hairstyles loose waves
Chunky waves balance out a wide brim.

Put that growing-out lob haircut to hard work by maximizing its layers. Dividing hair into sections, twirl each loosely around a curling iron, going in different directions, and shake them out for a tousled look. This gives your look more heft at the bottom, which effectively balances out a big-brimmed hat or other substantial headgear (side-eyeing you, pom-pom beanie fans!).

5. Rich Girl Hair

shoulder length hairstyles straight beanie
Lazy bends are made for the beanie life. Photo credit:

What to do when your hair is straight and prone to the dreaded hat head bend? Cut it off at the pass, that’s what. Styling straight shoulder length hairstyles with a loose, slightly lazy bend is the epitome of true effortless chic. It has a rather too-cool-to-care look, like you just rolled out of bed and had better things to do than struggle with your curling iron (which may or may not be a true story).

Editor’s note: Keep that annoying kink out of your locks after beanie-wearing by misting hair with a bit of texturizing spray or styling spray hat removal, then giving it an easy blast with a blow-dryer (or hand-tousle, if on the go). We like TRESemmé Between Washes Style Refresh All-in-One Styling Spray for both a quick conditioning boost as well.

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