
I get very excited when I see a trend that checks off three key benchmarks: I like it, it fits my lifestyle, and it fits my climate. AND, I tend to run with it. Or in this case, I am splashing through puddles with it. The chunky boot trend is one of the best things to happen to me in the last year.
I would not describe myself as trendy, but I do find trends fascinating to observe. (My thoughts are covered more extensively in this video on 2021 trends). Engaging in the just-right-for-you trends can lead to your style feeling updated, fun and fresh.
But more often than not these new shifts in style come with a learning curve. Remember when we were all trying to figure out how to style wide leg pants? Remember back even farther when we were all trying to figure out what shoes to wear with skinny jeans? I find the best way to speed up the learning curve is to PRACTICE! Set aside an hour or so to dive into your closet, and be prepared to try on numerous combinations. I love doing this (even though changing my clothes drives me crazy!) because the net return is so worth it. A few hours of styling and re-styling, and you have quickly learned how you like to wear a new style.
And that’s exactly what I’ve done in creating this blog post! As mentioned, I am a big fan of the chunky boot right now for its sartorial and practical merits. But how on earth does one wear such an overbearing-feeling shoe? Never fret my friends, I have several ideas and tips to share with you!
Outfit Ideas for Chunky Boots:
For the purposes of this post I’m styling two pairs: one very chunky boot – the Sinclair Platform Boot by Dr. Martens, and one lug-style boot, the Emi Lug Combat Boot by Freda Salvador (use code ANDREA15 to save!). The latter is still chunky, but I’d call it a bit more moderate.
1. Cropped Jeans + Pants

sweater / scarf / jeans / boots / bag


To me, this is the most clear cut way to wear big, chunky boots, with jeans or pants that are cropped enough to show them off! When I was combing through my Pinterest boards recently, I noticed almost all the pins with chunky boots featured a cropped hemline. This definitely showcases the boots in all their glory. It’s straightforward, and functional too, no ankles showing, and an inseam short enough to avoid puddles.
As seen by my overzealous amount of examples photos, I love wearing chunky boots this way. See examples of cropped pants in the photos below.

top* / pants* / jacket* / boots / bag is vintage // *gifted

2. Cuffed Jeans


merino turtleneck* / jeans / boots / bag / *gifted last season
This is essentially the same as number one, but with pants that are cropped via cuffing! Sometimes this look can feel ‘busy’ so I prefer a single cuff for a more streamlined look. If you have jeans that aren’t quite cropped length and want to still show off your boots, just flip up the hem. I also think chunky boots look great with full-length jeans, though it’s a vibe that some people need more time to warm up to.
3. Jumpsuits + Faux Jumpsuits


jumpsuit* (use LOULOVE15 to save) / cardigan* / boots / bag / *gifted
This one is SO fun! Many of us have jumpsuits in our closets these days, or even faux jumpsuits (two piece sets). I would even go as far as to say a sweatsuit or lounge wear set could be subbed in here too. (I have seen some very cool two-piece sets!) A chunky pair of boots is an EXCELLENT way to finish a jumpsuit outfit or make a loungewear set look intentional.

top + pants* (use ANDREAHARTMAN25 to save) / boots / bag / *gifted

4. ANY Dress or Skirt


dress* / trench (thrifted) / boots / sunnies / bag / *gifted
I feel like I am stating the obvious here, but chunky boots are spectacular to wear with dresses and skirts. You can pair them with long or short hemlines. (See chunky boots with a midi skirt here.) I love how boots like these can make a skirt or a dress feel really wearable in more inclimate weather. Style-wise chunky boots pair particularly well with dresses and skirts with feminine detail. Think: florals, full skirts, blousey sleeves, satin-y fabrics, etc.
5. Wide Leg Jeans + Pants

shirt* / jeans / boots / bag / *gifted
Chunky boots are an excellent footwear choice for wide leg jeans and pants because the high-volume shoe looks more proportional with the high-volume pant. This look can turn 2000’s really fast, so keep an eye on the supporting details to make sure they feel streamlined and modern.

top (old) / pants / boots / bag (no longer available)
If you’re in the market for some chunky boots, I’ve linked a few of my favorites down below. Most of these I have at least tried on. Also, shop the Emi Combat Boots here, and use ANDREA15 to save 15%.
My #1 Style Advice:
My biggest piece of advice: don’t be afraid to take risks. Enjoy the clothes you are wearing. Don’t be afraid to experiment, you can’t have reward without risk. Most of all: have fun! Life is so serious, but your clothes don’t have to be.
The sole purpose of style isn’t to showcase your figure or how cute you can make yourself look. It’s to showcase your personality, your creativity and communicate to the world around you the statement you want to make about yourself.