My 5 Most Worn Shoes this Winter

I can’t believe my wedding is now less than two weeks away. I’m starting to list out what to bring on the honeymoon and how much to pack. The goal is to fit everything in a carry-on. One thing I always struggle with though is bringing too many shoes.

Which, got me thinking about my favorite shoes in my closet versus the ones I wear the most. I certainly have somewhat of a work uniform I’ve created for myself. This includes wearing the same five shoes on rotation throughout the week.

This changes from season to season. Right now my most worn shoes consist of shoes that can be worn year round and ones that are winter specific.

So, I had the idea to think about my five most worn winter shoes and analyze why they’re my most worn. My closet contains more than five pairs so why are these the ones that get the most wear?

5 Most Worn Shoes This Winter

Suede Ankle Boots

My suede ankle boots are worn really frequently in the office or out to dinner. I like them for work because they dress up my causal outfits a bit. They’re pretty comfortable to wear and are actually decently warm. All my other shoes on this list are fairly casual so these get mixed in for the occasional days I want to add a heel or boot.

Suede Ankle Boots || Similar $198

New Balance

These New Balance shoes are so incredibly comfortable. I call them my dad shoes. I wear these when I walk to work if I plan on changing into shoes that aren’t so great for walking. Most of the time though I end up not changing out of them. These are also perfect for walking all over the city. Paired with thick, wool socks, it makes sense why these are top five most worn.

New Balance Sneakers || $80

White High Top Converse

Similar reasons to the New Balance shoes that I wear these a lot. These shoes I find a little more cute and less sporty though. It usually depends on my mood or how much walking I plan on doing when deciding between white high top converse or my extremely comfy New Balance.

White High Top Converse || $85

Everlane Day Glove Flats

These flats are my only black flats, my only flats I wear actually, and go so well with everything. They’re light, comfortable, and chic. Not the best for wearing outside during winter, but such a great shoe for the office.

Day Glove Flats || $115

Madewell Leather Oxford

I had been wanting a pair of Madewell leather oxfords for years and finally purchased a pair over Christmas. I deem it a good decision considering they made it into my top five most worn shoe list. They’re actually pretty comfortable with a pair of wool socks. I love the way they look really with anything.

Madewell Leather Oxford || $148

Outfit Details Stripe Top || Everlane Cheeky Jeans || Madewell Oxford


That’s the list! My five most worn shoes this winter. Before I wrote this article, I knew I definitely was wearing some shoes way more that others. It was fun to sit down and define them as well as analyze why it is I wear these certain ones so often.

The common theme: comfortable and versatile.

What are the most worn shoes in your closet?

You can shop the items in this closet and support Exploring Simple by using the affiliate links listed below.

Outfit Details

Stripe Top || Everlane Cheeky Jeans || Madewell Oxford

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