6 Cute Fall/Winter Outfits to Wear with Hats

Is it Fall yet? Who else is over the heat and so ready for Fall? I know, I know, I’ve been going on and on about the season, but I’m so excited by all the new hat trends and the fall/winter fashion that I’m going to wear. Even though the weather doesn’t quite compliment for a fall wardrobe yet, I do believe that getting a head start on outfit inspirations help to set my tone for the season ahead. And, a simple plan, some fall/winter outfit ideas give me an extra prep for how to maximize my current wardrobe and what more fall/winter must-haves that I need to stock up.

So I thought it would be helpful to give you my favorite outfit ideas to wear with hats this season. That way you’ll look cool but stay warm while doing so.

Dress: Similar| Sunglasses: SOJOS| Boots: Dr. Martens| Hat: Goorin Bros

Walk on the wild side with all animal prints have begun from spring/summer 2019 and there is no sign to slow down any time soon. I particularly love leopard prints because the color hues are screaming Fall.

The easiest way to plan your outfit that looks put-together every time is by determining a theme or having a visualization of the outcome in your head. With this look, I’d like to master a monochromatic outfit so I pick the bold leopard printed t-shirt dress to be the focal point of interest then built my entire outfit around that. As you can see one-tone dressing doesn’t have to be daunting, as long as you remember to add visual interest, depth or some multi-dimensional levels into your look. Don’t forget great accessories like boots and hats play a huge role in adding a nice dose of interest to complete the look. Yes, I love adding a pair of combat boots (wait, they’re the Doc Martens!) and a light coffee wool felt fedora hat to give it a cool twist of the ’90s.

Top: Mango| Pants: Zara| Jewelry: SiammPatra| Boots: DSW| Hat: Goorin Bros

The “no white after Labour Day” rule is an old saying, however with modern trends we can feel free to rock all-white outfits in the cooler months. I definitely love this trend, but instead of head-to-toe optic white I like adding with an eye-catching texture that really makes my outfit pop. In this look, pairing a button-down white shirt with a light cream wide-leg pants for a nice neutral palette. Then finishing with a timeless white wool felt fedora hat with chunky-heeled plaid ankle boots creates a winning combo.

Top & Jeans: Zara| Blazer: Calvin Klein| Sandals: Similar| Jewelry: SiammPatra| Hat: Zara

Red is definitely one of the autumn/winter 2019/2020’s most important color trends (based on Pantone NY Fashion Week color trend report) – it’s loud, it’s proud and it’s sexy. If you’re a little nervous about wearing all-red outfits, try a simple outfit with a pop of red accessories. For this outfit, I got inspired by the casual get-together effortless French. Simply tuck a basic striped tee into a pair of perfect fitting jeans (I personally love ripped jeans for revamping an unpolished look – I know I’m not an exact typically Parisian style!). Finish your look with a splash of color, an example would be a pop of red sandals and red baker-boy cap – and ladies, wear red lipstick!

Top: Similar| Jacket: Nordstrom| Skirt: Amazon Fashion| Boots: Prada| Hat: Gigi Burris

According to Google Trend Statistics over a 5 years period, “tulle skirt” was the most-fashionable trend to wear in Fall. Who would have thought that tutus are no longer reserved for ballerina and actually are street style favorite among celebrities and fashionistas? I channeled a rocker meets ballerina moment by toughening up a long white tulle skirt with a black moto jacket over a cute graphic t-shirt. I love high knee boots underneath my tutu skirt – a vertical silhouette of the boots make my legs look long and lean…and also sexy when they peek out from my skirt (you want to find a pair that is well-fit not lose – proportion is everything, girls!). Then top it off with an edgy leather newsboy cap to give as just playful and sleek finish.

Top: Similar| Suit: Mango| Boots: Marc Fisher|Sunglasses: SOJOS| Belt: Similar| Jewelry: SiammPatra| Hat: Goorin Bros

There is nothing I love more than a killer back-to-work tailored pantsuit that I can master from week-to-weekend. I’m a sucker for menswear inspired-take and a good power suit makes me feels powerful and influences how I view myself and how I view the world (ever heard the slogan, dress for success? it’s true). I own quite a few pantsuits in my wardrobe, but this season instead of inky navy or jet black pantsuits, I’m craving for fresh palette-neutrals with oversized proportion. For this outfit, I paired a really simple black lace top with a sand wool suit to keep everything modern and clean. Sidenote: if you’re too worried your oversized blazer looks too slouchy, a belt is the simplest, and best ladylike piece to cinch your waist and add balance into your look (and don’t be afraid to choose one in an interesting pattern or eye-catching color to enliven any neutral shade). In addition, you can enhance a sophisticated effect with a pair of white pointy boots. Head straight from the office to a girl date? Throw on the hat of your choice – mine was a shade darker than my suit to keep it classy and sophisticated. Now that you look so cool, so go out there and show what you can do (and one or two tequilas after work never hurts!).

Jumpsuit: Mango| Shoes: Fila| Belt: Michael Kors| Hat: Urban Outfitters

Jumpsuit is a way of life. It’s a one and done garment that makes it perfectly comfortable piece for a girl on the go who wants to look chic in a blink of an eye. And, with black as a choice of color, it never fails you. Style Tip: Remember that you need to be aware of your body type and try on something that brings about balance. A belt is a strategic way to visually separate the top from the bottom, giving some balance and structure to the outfit. The joy of going with a black jumpsuit (or any little black outfit) is that it will work with virtually any color or pattern when it comes choosing accessories: purple, red, blue, green, brown, pink…or animal print, you name it. People. Bucket hat is back and I am HERE. FOT. IT. So I finished the look with the fuzzy leopard printed bucket hat (It’s so soft – I can replace it with my pillow!), it’ll be the easiest outfit you’ll ever put together.

PS. Did I tell you yet I’m a fan of jumpsuit and anything leopard print?

Not sure what hats to purchase for fall? Read my top 10 hat trends you can’t live without this fall/winter 2019.