Published on September 14, 2018 — Leave a comment

Master Every Fall Look With These 4 Items

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Ever look at your closet and think, “I have nothing to wear”? Getting dressed in the morning does doesn’t have to stress you out. Check out this easy fall outfit formula that can be easily tweaked to make a cute look everyday of the week. We already created an easy-to-follow denim jackets outfit formula, now check out this guide for an effortless chic look with booties.

It’s time to say bye-bye to summer sandals and hello to fall booties! Booties are the perfect fall shoe because you can wear them no matter what kind of day you’re having. If it’s raining, there’s a bootie for that. If it’s windy, there’s a bootie for that. If you work in an office, there’s a bootie for that. If you going out, there’s a bootie for that!

With so many different bootie styles, it can be hard to know what tops and bottoms go best with them. Don’t worry! We asked lifestyle blogger, Madeleine Raiford-Holland, to create a fall outfit that could work for any and everyone. Use this super easy, 4-step bootie outfit formula all season long to make getting dressed a breeze. Whether you’re running out of the house, or taking your time in the morning, this outfit formula will create a stylish and weather-appropriate look every time.


Madeleine Raiford-Holland is a travel and lifestyle blogger from Vidalia, Georgia, a small town close to Savannah. Her blog is called Moderately High Maintenance, and she explains that she “serve[s] women by helping them save time and money by curating [her] favorite experiences and products at the best prices.”

Madeleine’s Style in Her Words:

I would say my style is more classic and less trendy, but I like to incorporate trends on my own terms. I love browsing magazines and seeing what my fellow fashion bloggers are wearing to see how I can incorporate trends into my personal style.  My outfit must work for me, not the other way around. No one has time for clothes that aren’t practical or don’t fit. I have a hobby farm with goats and chickens so if I can’t move in my clothes they aren’t the clothes for me!

In South Georgia, it’s hot (like 90 degrees) into October so our trends reflect our climate. Our trends include lightweight fabrics in dresses and tops and lots of layering! I try to make my warm weather fall look seasonally appropriate by bringing in “warm and toasty” fall colors like burnt orange, burgundy, and red. Booties are my one must-have for the transitional season! They look great with dresses and pants.

How to Wear Booties All Day, Everyday this Fall

STYLING TIP #1: Start with Booties


Booties are a perfect year-round shoe so they are essential during the transitions between seasons. So whether you like black booties, brown booties, or patterned booties, they can always serve as the anchor for your outfit. Madeleine bases the colors of her accessories on the shade of her booties. This styling technique will always tie your look together, making even a casual version of this outfit look polished.

Madeleine says:
My rule of thumb to tie a look together is to be consistent with an anchor color. In this case my anchor color is black with my jacket and booties. As long as your anchor color is consistent you are sure to look effortlessly pulled together!

STYLING TIP #2: Cuffing Season


Depending on the color of your booties, you may want to experiment with the wash and fit of your jeans. Madeleine opted for a dark wash with her black boots. We love this combo because it elongates the legs and creates a cohesive look. If you want to learn about which jeans go best with which shoes, check out our last post: Find Out the Top 6 Jean and Shoe Pairings.

Madeleine says:
I styled this look by choosing a classic denim skinny jean. Cuff your jeans to show off your booties and give your outfit a more casual feel. I got these perfect pair of Paige skinny jeans at thredUP.

STYLING TIP #3: Play with Patterns


Patterned blouses are the perfect top for transitional weather. From lightweight silk to comfy cotton, they are essential for layering. Because there is an endless selection of patterned blouses, you can create a ton of different outfits just by swapping out the top. Though the booties are the anchor of the outfit, the blouse is your opportunity to bring in a pop of color or pattern.

Madeleine says:
I love that this top is made of a lightweight material because it is perfect for layering during the fall transition. I love adding a knot to the bottom of just about any shirt. You don’t need anything extra and it draws the eye inward for a flattering silhouette.

STYLING TIP #4: Layer Up!


The final step is adding a stylish jacket. For this outfit, a solid, black jacket worked perfectly to balance the pattern of the top. If whether is a little warmer in your city, you can try a denim jacket. Read our denim jacket outfit formula to learn how to incorporate a jean jacket into your fall looks in 4 easy steps.

Madeleine says:
I finished the look with a black leather jacket and added a belt in my anchor color for a more tailored look. The knot in my top at the waist is perfect because it is the same length as my jacket, helping accentuate my waist.

As you get more comfortable with this outfit formula, you can make adjustments that fit your personal style. Maybe your boot will have a leopard print or perhaps the jacket will have some patches is on it! However you decide to style your fall looks, you can always come back to this bootie formula to get ideas.

Let us know in the comments below, which style of booties is your favorite? Black or brown? Flat or heeled? We would love to hear from you!