I’m a bit embarrassed to admit this, but once upon a time I used to regularly have two pairs of shoes — flats and heels — on me almost all of the time. I preferred the look of sky high heels, but would always keep a comfier pair stashed in my bag for when I needed to walk. It was inconvenient and honestly a big hassle, but back then my priorities were a little different than what they are now!
It’s been a few years since heels were my preferred form of footwear. Nowadays comfort is key and, especially since Miles came into the picture, practical shoes have become even more important. After all, comfort and versatility are key when handling a baby and all of the things that come with it! The important things for my shoes these days are that they’re not only comfortable, but also durable and non-slip.
That being said, here are the pairs I’ve had on constant rotation all winter long. In addition to the fact that they’re all well made and suit my current lifestyle, they also align with my personal style and work pretty seamlessly with my wardrobe. If you’re in the market for a good pair of shoes, these are my picks!
Veja V-10 Sneakers | The first time Brian saw these he said they looked like the sneakers of a 90’s teenager, but I definitely took that as a compliment! Veja shoes seem to add cool factor to even the most basic black denim and white tee. These did take a few wears to break in as they’re made from a stiffer leather, but they’re now my go-to shoes for everyday. I like that they’re wide enough to accommodate my flat feet, and the structure actually provides good ankle support for longer walks.
When I wear them: On a daily basis as long as it’s not raining too hard. I prefer these when I’m wearing a lighter coloured bottom, as they’re more flattering on the leg than a heavy black boot.
How they fit: Slightly large. I went with my regular size and I have to wear thicker socks with them – I could’ve sized down half a size.
Everlane Rain Boot (c/o) | Though these aren’t the sleekest looking pair of rain boots on the market (Alice + Whittles makes some good ones if you’re looking for something a bit more feminine), they sure are comfortable! If you haven’t already noticed, I’m a big fan of Everlane’s shoes, and the brand has managed to make a pair that don’t feel super clunky on and have a good amount of cushion inside. The tabs make for easy on-off, and they feel nice and snug around the ankle area. I’ve often found with rain boots that it feels like I’m lugging around big rubber tires and, while these aren’t the lightest shoes I own, that’s not the case with these. They’re also a good price point!
When I wear them: Whenever I know I’ll be walking somewhere muddy or rocky. They’re super easy to clean and maintain, and they have good grip. Oh, and I also wear them when it rains I guess 😉
How they fit: True to size if you plan on wearing thick socks with them. As Everlane says, they’re “made to be worn in your usual size with thick winter socks. Otherwise, size down.”
Frye Samantha Hiker Boots (on sale) | A couple of years ago, I convinced my husband to invest in a pair of Frye boots after he went through several pairs of cheaper leather boots in just as many years. He tends to really use the things in his closet and can wear them out rather quickly, so I’ve been really impressed with how his Fryes have held up: they look even better now and have aged beautifully! This year, when I was looking for a pair of cold-weather boots, these caught my eye. As far as a winter boot goes, I think these are pretty chic! I’m not sure how they’d fare in a colder climate, but they’re perfect for staying warm and dry in our West Coast winters. The only downside to these boots is that they take a while to put on and take off, which can be a little annoying with a baby.
When I wear them: In the snow, and on winter walks with Miles when I know it might be a bit slippery out.
How they fit: True to size. I usually size up for boots, but not for these; the shearling lining means I can wear thin socks and still stay cozy and warm.
Acne Jensen Boot | The Jensen boot by Acne is definitely an investment, but by now they’re also a classic. This is my third winter with them, and they get just as much wear as they did in the first year. The pointed toe elongates the legs, and the pebbled leather feels luxurious and makes the leather more hardy. I also really like that the sole is rubber instead of leather like a lot of high end shoes. It makes me think that they actually thought of practicality and long term use!
When I wear them: All the time, with anything from denim to trousers to skirts. They’re super versatile and are able to withstand some rain as well.
How they fit: True to size
Everlane Boss Boot | I (fittingly) bought these for myself a few years ago after getting a promotion at work. Though I normally would’ve chosen the black, I went for the cognac since I already had my Jensen boots. Because of the black heel they’ve surprisingly gotten a lot more wear than I’d anticipated — they go with a lot of different looks! It likely also has to do with the fact that they’re hands down the most comfortable leather boot I’ve ever worn. Unfortunately this colour is no longer available, but they have several black options as well as a bone colour and burgundy.
When I wear them: Anytime I need to be a little dressier but still comfortable. The 2-inch heel makes them a bit more refined, but they’re still totally walkable. I love wearing them for date nights!
How they fit: A little bit small and narrow at the front. I sized up half a size.
There you have it: my top 5 cooler weather functional footwear picks! My shopping weakness is definitely shoes — so the ones that made this list really stood out for me. I hope these mini reviews are helpful; let me know if you want to see more posts like this!
Your Boss Boots are very cute and I can see how they would compliment many outfits. The pointy toe is something I haven’t worn in a long time, but guess I should reconsider that element in a shoe. Hmmmm. . .