Winter Headwear: 10 Transitional Styles from Day to Night
Categories: Fashion

Winter Headwear: 10 Transitional Styles from Day to Night

In a perfect world, you would have all day to prep for all of your afterwork party obligations. But the reality is you’re usually cramming a pair of heels in your tote bag, leaving the office late, hopping in a cab, and hoping for a red light to attempt a two-minute wardrobe change. And considering the weather as of late, chances are you’re sporting a winter hat and some DIY glamour gloves. So to help with the continued day-to-night wardrobe dilemma, here are a few ways you can wear your winter headwear all loving day long.

1. Knitted Bow Headband

Day: We love that a cute headband will look adorable with just about any sweater. Forget perfect curls, and let your hair stay in a tousled bun all day long. (via Not On The High Street)

Night: Let your hair down, throw on a cute bohemian dress, and you’re ready for date night. (via Etsy)

2. Neon Cuffed Beanie

Day: There’s nothing wrong with throwing on a sporty beanie with casual jeans for a day out and about, but go for neon over neutral to make a statement. (via Magnifique)

Night: Don’t be scared to pair your sporty beanie with your LBD (little black dress). We’re loving this look with a classic fur coat, studded slouch bag, and the perfect pop of pink. (via Lovely Pepa)

3. Faux Fur Earmuffs

Day: Keep your office attire classy with simple white earmuffs, accompanying a tailored blazer. (via GK Furs)

Night: Earmuffs glammed up? Yes, please! Take your earmuffs to the next level with a fun sequined top and flirty lace dress. (via American Eagle)

4. Wide-Brim Fedora Hat

Day: A floppy-brimmed hat worn just the right way can make any ordinary outfit sexy. Keep your hair loose and your makeup minimal, and let the hat do the talking. (via Free People)

Night: A fedora may not be the first accessory to come to mind for a party dress, but think again. With a loose, bohemian-style slip dress, it is more than a statement piece. (via ThreadSence)

5. Pom Pom Beanie

Day: Nothing says “winter” like a pom-pom beanie, and it’s one hat you can’t rock in spring or summer, so get good use of it now. Throw on with any oversized sweater (a cute yellow one at that). (via NK Diaries)

Night: No need to worry about hat hair here. Leave that head warmer on with your evening dress. We love this flirty-rocker style that the leather jacket adds to the look. (via Maritsa)

6. Scarf Headwrap

Day: For the days you don’t want anyone to see your hair or you overslept and simply didn’t have time, don’t be afraid of a headwrap. It looks great with bold makeup and bright lips! (via G-Star)

Night: Want a more formal look? Keep your messy winter hair masked, while wearing it down. A scarf wrap done right is cute enough to wear with a casual dress. (via Hello Fashion)

7. Vintage Fur Hat

Day: Nothing says warm (and stylish) like a vintage fur hat. Simply pair with denim and a puffer vest. (via Darling Two)

Night: We’re all about mixing prints and textures. Matched with gold glitter pumps, floral-print cigarette pants, and a subtle silk blouse, this fur hat completes the look! (via B Soup)

8. Wool Ball Cap

Day: If you don’t have a solid wool ball cap, it’s a definitely must-add to the wardrobe. It’s sporty enough for guys to love it and feminine enough to dress up. (via Moorea Seal)

Night: We wouldn’t recommend throwing on a ball cap with just any outfit, but if done right with a monochromatic outfit, a sleek black hat, and tailored mini skirt, you best be going for it. (via Fashionologie)

9. Slouchy Beanie

Day: It’s cold out! So stay cozy and comfy in the office with a slouchy beanie. The best part about slouchy beanies is being able to pull them back so your hair doesn’t get ruined. (via Free People)

Night: To pull this look off at night, there’s nothing more to do than copy this look that we’re totally loving. Pair a slouchy beanie with a perfectly pleated polka-dot dress. (via All Things Inspired)

10. Mens Cable-knit Beanie

Day: Your man can always make a simple cable beanie stylish with head-to-toe black. We love this layered look! (via Street Style Market)

Night: Men suffer the same wardrobe issues, transitioning from day to night with no hair gel on hand. Not to worry; an in-the-know fella will sport his winter hat with a tailored suit. (via Soletopia)

Which of these wardrobe-changing hats is your go-to look? Share your style tip in the comments below!