Style by Joanie

style post no.3: fall/winter boots

Dear readers, a few dated elements of my old theme broke last week. So I am reconstructing and reimagining this blog space. It’s not perfect yet. But seasonal footwear goes on, and we have a few favorites from my sister Joanie this week. Thank you Joanie!

Madewell Chelsea

Sam Edelman

Freda Salvador


Madewell Regan



LL Bean

Cole Haan

Okay, let’s do fall/winter footwear! Yes, I live in Los Angeles but I take several cold/snow trips every year to Michigan, New York and Colorado so I’m well versed in the subject. I have to keep my shoe lineup tight as I’m generally packing things in a suitcase and don’t have a ton of room. When I’m traveling, I like to bring one boot with a stacked heel that I can wear with pants or a dress with tights, one all weather boot that’s waterproof and a boot that’s weather appropriate but maybe a bit more stylish for when it’s cold but not sleeting or snowing.

Something that took me way too many years to learn is that when you’re investing in a boot or a shoe, take it to a cobbler and get the sole and heel re-enforced before wearing them. It will add a lot of life to your boots and also prevent you from having to do damage control down the line when you wear a hole in the sole. Many fall/winter shoes are expensive and should last you for years. Properly caring for them from the minute you buy them will help. This doesn’t apply to rubber soles, but ones like the Madewell or Everlane pairs below.

a. Madewell Chelsea

b. Sam Edelman

c.Freda Salvador

a. I went to Ireland in November and only brought a carry-on suitcase, these were the boots I brought with me and as you can see from the two photos below I wore them everyday with dresses and with jeans. They are chic and comfortable, I walked a lot in them. They recently came out with this version which I also love. The tough sole makes them extra versatile.

b. I also own these rain boots. They are a great price point and I like that they are more narrow than most options out there. I recommend ordering up a size. I only wear these with thick socks and don’t think they’d be comfortable without them. I also really like this option from Everlane.

c. This one is a pricer option but I’m a big fan of the shoes that Freda Salvador makes. They are a San Francisco based company that make their shoes in Spain. I have a pair and the quality is excellent. These boots are fully waterproof. I love the little bit of lift of the sole and the fitted upper. I linked them at Bloomingdales because they are currently 25% off and these boots never go on sale!


e.Madewell Regan


d. These boots are not weather proof but they are a very flattering and a fun option for the fall. They have tons of great colors and I recommend picking any of them but the bone color which looks like you’re wearing socks. The black is your safest bet and will give you a great long line when wearing them with dark pants.

e. I own this boot and love them. I have recommended them to so many people. They look good with jeans or dresses. I’ve worn them in all types of weather and they pair wonderfully with socks peaking out of the top or with no-show socks. This is one of the times I wish I could have gotten the sole and heel reenforced before wearing them but they are still holding up well 3+ years later.

f. I’ve become that person that travels with a pair of slippers. I wear them all fall and winter, even in California and there is something about having your own pair when you travel that’s comforting. These Uggs are my favorites. If you want cozy feet and don’t have room to pack slippers, these are my favorite socks. They have grips on the bottom which is a nice touch for walking on wood floors.


h.LL Bean

i.Cole Haan

g. Sorel knows a thing or two about winter shoes. I love this pair, they make a version of it every year and it sells out quickly. This is a serious boot that can see you through low temps and snowy days.

h. No cold weather shoe post would be complete without this classic pair from L.L bean! This boot has been around for ages, they are timeless. You can wear these for years and they’ll always be in style. Make sure to pay attention to their sizing tips that they offer. They also come in a high version but I personally like the low one best.

i. And this surprisingly lightweight and very comfortable pair from Cole Haan which I also own and love (I guess I have a lot of boots for someone who lives in LA). I personally love the winter white color but the black would be a safer option. I wore them all over Telluride last winter and didn’t get cold toes!



Hansel from Basel

One very important last note: socks play a big role in fall/winter footwear! I think the chunky knit sock is underutilized. I love this pair from J.Crew and own it in every color. I pair them with ankle boots and jeans or pants that are fitted all the way down. I like the sock showing.

It can get repetitive wearing the same pair of boots all winter long, socks are a fun way to mix it up. I also like these from Amazon. And for other fun socks, I’m into Hansel from Basel.


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