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Teacups and Things

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Weekend Casual: How to Dress Up a Baseball Cap

October 31, 2017

I’ve said it before, and I’ll say it again: fall is my favourite time of year. I seriously hate having to dress for the weather like in the summer and winter. Fall is the perfect season – it’s not too hot, and not too cold. I also love wearing layers, fashion hats and fall clothes is perfect for this.

I’ve always loved hats. I don’t wear them too often because if I’m being perfectly honest I have a small head. Like, it’s child size. I’m not kidding. It’s usually a bit easier for me to find hats in the summer, because a lot of the straw hats have those adjustable strings on the inside. When it comes to fall fashion, I’ve always felt a little limited in my hat choices.

You’d also think that someone with a small head would be okay with most baseball caps – well not this kid! I often can’t adjust baseball caps small enough, and when I do there is always so much excess fabric from the strap. When I found this cap from Tobi, I was thrilled because you’re able to hide the extra fabric from the strap through a grommet that goes to into the liner of the hat.

For a gal with a small head, this was the best thing ever.

(Hat: Tobi, Outfit: Zara, Tote: Chapters Jewelry: Stella & Dot, Shoes: Globo)

I’ve also been looking for a solid black baseball cap for a long time. I really think it’s a must-have item in any closet. I love how hats can transform an outfit, and I’ve always felt that basic baseball caps often get overlooked. 

They are the perfect addition to any sporty chic outfit, plus they’re handy when it’s sunny out! I styled my cap with my favourite dark wash skinny jeans from Zara, along with a long cardigan and faux leather loafers.

I’m really looking forward to styling more looks with this hat, so keep an eye out for that. I love when baseball caps are styled with heels, for high-drama sporty chic look.

What are your thoughts on the basic baseball cap, overrated or underrated? My vote is underrated. There’s just so many ways to style them! Let me know your thoughts and if you have a favourite way to style your fav baseball cap.


While this post was created in collaboration with Tobi.com and I was gifted items mentioned in this post, all of the opinions expressed are of my own.

casual outfit fall fashion fall outfit fall style fashion OOTD style Tobi what I'm wearing
by Kait 
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Hello, I'm Kait! A Canadian lifestyle blogger from the greater Toronto area, living life gluten-free. I'm passionate about supporting local communities and collecting teacups.

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Teacups & Things is a Canadian lifestyle blog written by Kait. She lives in the Toronto area in Ontario with her King Charles Cavalier. Topics include: fashion, beauty, local community events, food, gluten-free cooking, home decor, shopping, DIYs and much more.

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