Home Fashion 5 Fall/Winter Outfits: Styling My Favorite Shoes

5 Fall/Winter Outfits: Styling My Favorite Shoes

by How She Styles

I picked my top five shoes of the season, and decided to create fall/winter outfits. I love how each look turned out and I hope you do too!

Dr. Marten Boots

My doc martens are my favorite shoes that I own for many reasons. First, they are super comfortable. They took about one wear to break in, and then it was like putting soft leather gloves on to my feet. Second reason that they are my favorites is that I don’t have to consider the weather when I wear them. At least most of the time. Obviously, I cannot wear these when it’s too hot, but otherwise any type of weather is fine for these boots.

I don’t have to worry about rain or snow because these are waterproof and I can vouch for their effectiveness at keeping water out. Finally, these shoes make me feel like a badass. I could be wearing sweatpants I would feel like I could conquer the world if I am wearing these boots. That my friends is the power of fashion.

With this idea in mind, I decided to lean into the edgy style of these boots, and go for a look that would make me feel powerful. I started with these leather pants that I thrifted to add to the to edgy look that these boots are already giving. To complete the outfit I went with a plaid shirt from Uniqlo to give a bit of color contrast. I personally love how a button up shirt buttoned all the way up looks so that is how I styled it. To finish the look I painted on a dark lip to add one more element of edginess.

& Other Stories Loafers

Next pair of shoes are these monk strap loafers that I bought secondhand in 2019. They are originally from &Other Stories which is a brand I absolutely love, but always felt that it was too expensive for me to buy new. When I found a pair secondhand in my size I actually gasped in the store and I have been wearing them ever since.

girly fall/winter outfit

I love wearing loafers. If I am between wearing a pair of ballet flats or a pair of loafers I will always choose a loafer. Which made these the perfect addition to my wardrobe. I was also drawn to was the mixing of textures and the color. To me, these shoes don’t look like anything else that I own, I love that they feel unique. I decided to pair them with these green Everlane pants because I love the way purple shades mix with green. Then I finished the look with a cream sweater with a feminine ruffle collar and balloon sleeves to contrast the masculine details in the shoes.

Blondo Booties

These are a pair of boots that are weatherproof so I love wearing them in the winter. This taupe color is a nice addition to my wardrobe because all my other boots are black or brown.

casual fall/winter outfit

I love pairing these boots with creams and browns to give a neutral cozy look. For this outfit I paired these boots with a rust colored Madewell dress to add a feminine touch to these more masculine boots and then made it fall ready with a cozy cream tunic length sweatshirt.

Franco Sarto Loafers

These are a shoe that I love wearing because they are a super soft suede that is really comfortable to walk in. The color is really what sets them apart from everything else in my wardrobe.

For this outfit I decided to contrast the green shoes with a red top and make this an outfit that could work for Christmas. To finish off this outfit I chose a pair of jeans with no distressing to make the other two pieces the stars of the look.

Aldo Boots

These are another pair of boots that get a lot of wear in my wardrobe, but have a completely different look from the other two boots from this list. I love the high boot shaft and the super pointed toe on these. They elevate any outfit I wear them with.

Dressy fall/winter outfit

I generally wear these boots casually with jeans and a tee so for this look I decided to try to put together a dressier outfit. I started with the Uniqlo skirt to mix two different textures that are the same color. Then added to black tights to connect the two pieces. I finished off the look with a black and green printed Zara blouse that added an elegance to the entire outfit.  

I hope you guys loved the outfits I put together, let me know which outfit was your favorite in the comments.

Want to see more styled looks, check out some of my other posts

Wear To Work Monochromatic Look

Orange and Purple and Blue Oh My!

Contrasting Colors For Fall

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