Styling Boots for Fall 2025 | EP 261

Hey Fashion Besties – it's time to kick off pre-fall in style! 🥾🍂 This week on WEAR THIS NOT THAT, we're tackling one of the biggest questions Holly gets every season:

❓What boots are in right now, and how do you style them without committing a fashion crime?

Look no further, this episode is your one-stop boot styling masterclass for Fall 2025.

Read on for your complete boot style guide:

Whether you're a thigh-high trendsetter, a cowboy boot queen, or a bootie enthusiast, we are spilling ALL the style tea on which heights, shapes, and finishes work for your body type, outfit goals, and lifestyle.

Plus – how to care for your boots so you can rationalize the CPW- cost per wear. This episode breaks down the possible sting of paying for a pair of quality boots. 

📺 Watch the episode on YouTube
🎧 Listen wherever you get your podcasts
📸 Follow along on Instagram: @wearthisnot_that
🛍 Shop curated looks: www.wearthisnotthat.shop

🔥 Your boot style guide is here on your Pinterest board 

WHAT WE COVERED THIS WEEK:

Over-the-Knee + Thigh-High Boots

o Best for taller frames (5'6" and up) or those with slender legs.

o Works with shorter dresses, maxis, midis, or over skinny jeans.

o Materials: leather for structure, suede for comfort and softness.

o Pro Tip: Make them the star of your outfit—keep the rest simple.

Knee-High Boots

o Universally flattering for all heights.

o Creates a long, lean look when paired monochromatically with leggings, skirts, or dresses.

o Includes tall cowboy styles and slouchy/pirate boots you can wear up or scrunched.

Mid-Calf Boots

o Most common cowboy boot height.

o Authentic cowboy boots pull on. No hardware needed. 

o Cowboy STYLE boots have zippers or hardware for easy access. 

o Never go out of style and work for any age or gender.

o Style over jeans or with dresses to dress down a fancy look.

Ankle Boots / Booties

o Perfect under jeans, with leggings, or tights.

o Must fit snugly at the ankle—no gaping or blister-inducing tightness.

o Avoid cropped jeans + short booties combo for a cleaner line.

Boot Fashion Crimes 🚫

o Weather boots when it's not rainy/snowy.

o Out-of-season shearling boots.

o Poorly maint