Styling Boots for Fall 2025 | EP 261

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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 maintained, scuffed, or damaged boots.
o Loud rain boot prints (polka dots, ducks) in dry weather.

Boot Care 101

o Find a great cobbler to keep them in rotation for years.
o Use leather conditioner + water/stain protectors.
o Always store them properly to maintain shape.

✨ Featured in this Episode:

• Chocolate + Cream Lanai Skirt from the Wear This Not That Boutique—perfect with tall boots.
• Della Denim Trousers (Mid-Wash + Indigo) and matching Indigo Blazer—your new boot-friendly denim staples.
 

 

Fashion Besties—DM Holly your boot questions, send pics of your new fall looks, and let us know which styles you’re rocking after this week’s inspo.

Head on over to our IG and your Pinterest board for more boot style inspo!   💃👢

 

Check out this episode!