October 27th, 2015 at 2:00am

Another fall season means another set of fall hats (and apple cider doughnuts).  But how do you decide between a wool fedora, a beanie or a baseball cap? Well, head shape, hair and climate play a major factor but isn’t it also about what’s going to look good with your new fall boots and multitude of layers?

In an effort to help you narrow down the choices, we asked some of our Style Gurus what hat they think is perfect for fall. Let’s see if any strike your fancy (and head size).

1. Squad Hat

Alexa Roberts Hat Pick


“This hat is currently my favorite hat for the fall. I love this baseball cap because it is the perfect way to coverup a bad hair day with a touch of style. My outfits tend to be very minimalistic so I love to wear this hat with black ripped jean, sneakers and a leather jacket to add to touch of color.”- Alexa Roberts, Syracuse University

2. Genie by Eugenia Kim Alex Cap

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“This gray felt cap will add a more casual vibe to my dressier fall outfits. I would pair this with a slouchy robe-style coat and sneakers.”- Christine Enriquez, Loyola University Chicago

3. Brushed Fair Isle Slouch Beanie 

Kayla Boyd

“I think a slouchy beanie is the perfect hat for fall because they create an effortless, stylish look that is sure to keep you warm and cozy. Also, there is no better way to cure a bad hair day!”- Kayla Boyd, Eastern Michigan University

4. Felt Hat

Storm Tyler Hat Pick

“Hats are one of my favorite staples and purchased based on versatility. This selection is ideal for frizzy curl days, as a chic accessory to a night out or to add spice to a daytime ensemble!”- Storm Tyler, Texas State Universty

5. Higher Summit Hat

Tess C

“These types of hats are an absolute staple in my wardrobe for the fall. You’re outfit is kicked up a notch the moment you put it on. I just love how effortless wide brim hats are, and they are incredibly chic. I love the ones from FreePeople because I find they are the most similar to rag & bone!”- Tess Cvikota, DePaul University

6. Wide-Brim Wool Hat

Taylor Shanie Hat Pick

“I chose this hat because it is perfect for fall! The burgundy color is such a classic choice and can match well with neutrals. The leather strap detailing is also great because it gives the hat a ’70s vibe, which is extremely popular this season.”- Taylor Shanie, FIDM

7. Wool Slouchy Femme Cap

Eliza Huber

“I can’t help but love anything retro and ’60s-inspired. This hat could be worn with so many different styles and colors that it is definitely a must-have in every Fashionista’s wardrobe. Match this with a suede mini dress over the top of an ivory turtleneck with tights and some Mary Janes and you’ve got yourself a totally chic, old school look.”- Eliza Huber, University of Iowa

8. Wide Brim Fedora

Kara Ng

“If you follow me on social media, I am ALWAYS wearing a wide brim fedora, but mine is more for the warmer seasons. For the colder seasons, wool is a better fit because it’ll add some extra warmth for your head. With my head being on the bigger side, wide brim fedoras are a lot more flattering. I love how by simply adding a wide brim fedora, an outfit can look so much trendier and fashionable! It’s such a simple accessory to throw on to complete a look.”- Kara Ng, St. John’s University

9. Wool Fedora

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“A felt fedora in a pretty jewel tone feels luxurious for fall.”- Allie Barke, DePaul University

10. Wool Boater Hat

Maria Gomez

“The small brim on this hat helps adds pizzazz to my outfits without being too over the top (pun intended). I love pairing this hat with a black turtle neck and red lip combo for a more sophisticated look.”- Maria Gomez, Hunter College

11. Round Beret

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“I picked this hat because I am so in love with the resurfacing beret trend. This would nicely complement a sleek leather jacket.”- Crystal Hodge, University of Georgia