Overcoming Hat Paranoia: How to Wear a Floppy Hat in the Fall

Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | Floppy hat outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante

I’m approaching 30, and it blows my mind how insecurities still get the best of me. I’ve been through years of therapy from my eating disorder— and I still think I look fat in certain jeans, I still turn to the side in photos to make my hips look smaller, and (up until recently) I refused to wear hats because I believed they made my face look large. Since they have such an awesome return policy, I took a leap of faith on this floppy black hat on Amazon. I’m so glad I did. I love it, I feel confident in it, and it’s the perfect way to compliment a basic fall ensemble. Plus, it keeps my ears warm on frosty fall mornings! If you’re unsure of how to wear a floppy hat in the fall, this post is for you!

My mom was 100% right. Clothing really is more about confidence than anything else. Even though there are pseudo-scientific studies about choosing the right hat for your face shape, I personally believe it’s all about your attitude. If you say “ew, I hate the way I look in hats,” others will think you look weird in hats. They’ll buy into your hat paranoia. Odds are that you look fabulous in hats; it’s just a mental hurdle you have to clear. After taking the plunge myself, I styled this casual fall outfit for the pumpkin patch last weekend. Kyle and I had so much fun playing with pumpkins and getting lost (literally) in the corn maze at Lloyd’s Pumpkin Patch. Head to the bottom of this post for full outfit details!

Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | Floppy hat outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | Floppy hat outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante

If you’re looking for a durable designer bag, the Tory Burch Nylon Ella tote has been my go-to since college. I’ve lugged books, clothes, computers, you name it in this bag! Plus, it’s actually one of the most affordable Tory Burch bags you can buy. It’s $198, which I recognize is still pricey. However, after 7+ years of use, I can testify that it’s worth every penny.

Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | Floppy hat outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a DebutanteBlack floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante

How did these pictures find their way in here?! I had fun taking some shots of my hunky Banana Republic/J.Crew/North Face model slash boyfriend, Kyle. Check out his brand new book Pocket Guide to Action on Amazon!

Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante

So, next time you’re curious how to wear a floppy hat without making your head look weird or your face look fat, silence those insecurities. Wear the hat you want to wear– in the way you want to wear it. My counselor once taught me to use the “BFF rule.” If your best friend wanted to wear a hat but was afraid it would look funny, what would you say? You’d say, “Um, what? You’re beautiful, and you’ll rock that hat.” My remedy for overcoming hat paranoia? Being my own best friend. 

Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a Debutante Black floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a DebutanteBlack floppy hat with leopard crewneck sweater, J.Crew Factory blue gingham button down, black jeans, Nine West tall black boots, and a Tory Burch Ella tote | Comfy and casual fall outfit idea | Floppy hat outfit idea | How to wear a floppy hat in the fall by fashion blogger Stephanie Ziajka from Diary of a DebutanteShop the Look: Leopard Crewneck Sweater, $75 (currently on sale and available in a black print, as well) | Navy Gingham Button Down, $28 | Black Skinny Jeans, $80 | Tall Black Boots, $189 (these are a few years old from Nine West, but I’ve linked an almost identical style) | Black Floppy Hat, $27 (also available in beige, brown, and burgundy)| Black Tory Burch Nylon Tote, $198 | Gunmetal Drusy Elisa Necklace, $65 (also available in over a dozen different color combos)


 
Last, but certainly not least, Happy Halloween, y’all! What do you have planned for this evening? Kyle and I are probably going to stay in, drink apple cider bellinis, and finish Stranger Things. Can’t complain!

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