Last week I wrote a post about shopping for clothes you’ll actually wear and talked about knowing  something is a must-buy when the need nags you.  I recently noticed my own nagging need that I want to touch on today: casual shoes that I can wear in the winter for doing things like running errands and quick trips around my Brooklyn neighborhood.

For the most part I am well covered in the casual shoes area. On super freezing days I will usually put on my classic UGGS, when it is snowing I will wear my Sorels, and on inclement rainy days I love my Sam Edelman chelsea style rain boots.  Once the weather gets a bit warmer, I usually grab my ballerina flats or my suede oxfords, and during the summer I am good with my Birkenstocks or Fit Flops.  Yet, I have found this tiny sliver where I am not covered; shoes for mild winter days where it’s too warm for my UGGS, not inclement enough for my rain or snow boots and not yet warm enough for my ballerina flats or oxfords.  I found myself grabbing my tall cognac boots, which is fine, but considering my daily morning errands can be accomplished within a two block radius, and then I’m back home to work for the rest of the day when not seeing clients, I have a nagging need for a casual pair of comfortable shoes or boots that I can easily slip on and go.   They don’t have to be super stylish or glamorous, just functional, practical and not ugly.

So I went on the search for shoes that could fit this area of need and, knowing I can’t be the only one who finds themselves lacking in this particularly specific shoe area, I decided to share my findings.

Casual Shoes You Can Wear in the Winter


casual shoes

I started with these chelsea boots from Miz Mooz because I am actually happy when it is rainy outside.  My cheslea style rainboots are so easy to slip on that I have been wishing I had the same pair in leather.  This is the type of casual shoes I am looking for, styles that I can just slip on.

For this casual look, I used these skinny jeans from Lucky Brand, a basic burgundy sweater from Ann Taylor, casual grey bag from Kipling, stud earrings and printed scarf from Halogen to wear with the boots.


casual shoes

Theses booties from Dankso also got my attention because they’re likely comfortable (they’re from Dankso, after all) but they’re not clogs.  In fact, I have seen a lot of women wearing booties like this around my neighborhood.  I like that they look easy to slip on and have a slight heel but aren’t high.  I don’t need a pair of heels to walk a few blocks.

For the rest of the look, I added these skinny cargos from J. Crew, v-neck sweater from Modcloth, a casual Baggallini bag, this whimsical mermaid necklace and leather wrap watch from Tory Burch.


casual shoes

Even though I don’t personally wear black, I know most people do, and I liked the style of these boots from Anthropologie.  They’re flat and can be slipped on.  This is the level of ease I am looking for.  No buckles, zippers or even lacing up.  You just put them on and go.

I styled these boots with a pair of ponte leggings from Theory, a relaxed funnel neck sweater from Madewell, burgundy scarf from Zappos and black tote from Topshop.


casual shoes

While on my search for casual shoes I seriously started to question if there are actually shoes out there that are easy to slip on but aren’t dorky looking.  I have to say, the pickings are slim.  It’s hard to find casual shoes that aren’t boots.  Not that I am against wearing boots all the time, but not everyone wants to exclusively wear boots.  It was then that I found this easy-on style from Modcloth.  They’re actually sort of cute and will certainly work for a quick trip to the corner for milk or for getting some things done outdoors before I start my day.

With these shoes, I styled this outfit with ankle length skinny jeans, a classic white button down, cardigan from Zara (sold out), small brown handbag, simple drop earrings from Ann Taylor and bracelet from Banana Republic.  Obviously, I wouldn’t get this accessorized to pick up a gallon of milk, but wanted to evolve the outfit beyond just the basics.


casual shoes

This last pair from SoftWalk I chose because they looked like the perfect hybrid of a stylish pair of booties but with a soft rubber sole.  You kind of get the best of both worlds, super functional, comfortable yet stylish.  Plus, they’re from a well known comfort brand.

For the look above, I added these dark brown skinny jeans from Madewell, a printed top from Modcloth, Uno de 50 earrings, an orange beaded bracelet from Stella & Dot and bag from Dooney & Bourke.

Rarely do we think about wardrobe needs when it comes to total function, yet find ourselves without these basics that may not be the height of fashion but still have a place in our closets.  We all have a need for casual shoes to get us from point a. to point b. and with the styles above, there actually are shoes out there that can enable us to do get to where we need to go in style.