My Cold Weather Shoe Wardrobe

If you subscribe to Wardrobe Oxygen and received my first exclusive content monthly newsletter, you know I worked on updating my closet for the season. A lot of you replied back to the newsletter saying you used my tips and also updated your closet. And like me, you may be looking at your cold weather shoe wardrobe and seeing some… opportunities for improvement.

My Cold Weather Shoe Wardrobe

There are some cold-weather shoes I've owned for years that continue to treat me well when the temps drop. However, I do find the need to update my wardrobe a bit to fit with the new trends and silhouettes and to replace those that can't be repaired or buffed up by my local cobbler. I thought it may be helpful to see my cold-weather shoe wardrobe.

For reference, I am a 49-year-old solopreneur who works from home or her office space in town. My job requires me to dress up on occasion, but in general I live in a casual to business casual wardrobe with shoes to fit. Especially after Lockdown, my focus has become on lower-heel shoes with comfort and support. That being said, I am a fashion lover and will whip out a comfortable heel when I know it really makes the look.

The Winter Replacement for the Birkenstock Arizona

From late spring to early fall, my go-to shoe is the Birkenstock Arizona. I have a few pairs in different colors to wear with dresses, jeans, shorts, and trousers. My feet love these shoes, and when I wear them I don't wake with back pain. However, they don't offer enough coverage and warmth for cold weather.

Last winter, I tried a couple of different Arizona alternatives and they all were wrong. Not roomy enough for my feet, made from synthetic materials that made me sweat, not enough grip on the bottom to feel secure on cold, damp pavement. With the popularity of clogs this season, I thought I'd have an easy time finding a good winter alternative. Notsomuch.

I ordered the Birkenstock Boston, and they looked really goofy on me (the proportions were all wrong). I tried similar styles from other brands (even wide-width options), and they were all too snug or had sweaty plastic footbeds. Dansko clogs made me feel wobbly on my feet. The chunky versions of Birkenstock mules and clogs looked cartoonish on my short, curvy frame and felt heavy. On a whim, I ordered these clogs from SoftWalk, and they're exactly what I was looking for:

• A brown that would go with camel, cognac, and chocolate belts and bags and wouldn't look bad if they get scuffed and worn
• Soft leather that would fit my wide and high volume feet, even when wearing thicker socks but not so thin they stretch out
• A lightweight sole that offers a bit of lift
• A footbed that isn't plastic and has arch support
• No goofy buckles or textures or hardware or finishes
• A silhouette that fits my feet without looking clownish

I got the color luggage; I usually get an 8, but if a shoe is wide, I've been able to go down to 7.5. I got an 8 W, and they are perfect for me, but they may be a tad short for others. If in doubt, size up. They are soft right out of the box, the sole looks like cork but is lightweight cushioning rubber, and they look expensive and not like “comfort shoes.” They are also cheaper than Birkenstock and Dansko (less than $120).

The SoftWalk Arvada Clog is available in four colors and three widths at the SoftWalk site, Nordstrom, DSW, Amazon, QVC, and The Walking Company for $119.95, Zappos for $94.80 (but limited selection), and Macy's for $83.97 (reduced options for colors and widths).

Some asked what socks I wear with clogs, and I wear fun socks, and when it gets colder, I choose a thicker sock with wool, and usually something marled, a fun color, or with a print. Some suggestions:

The Trendy Low-Profile Sneaker

Over the summer, I was a big fan of the New Balance 327 as my trendy sneaker, but I found the proportions wrong on me when wearing wide-leg and flared jeans (what I usually wear). I wanted something low-profile, and I didn't want white or black. Veja shoes are usually too narrow for my feet, but reviews said the Volley O.T. ran wide, so I took a chance.

The Volley O.T. from Veja comes in a range of colors; I was immediately drawn to the weird color they call “Liquor” that if it is a liquor it's absinthe or chartreuse. The color is so random it goes with nothing which means it goes with everything. They truly are wide enough for my feet and also feel really good!

I've had them for two months and wear them at least three times a week. While I wouldn't choose them to go for a hike or sightseeing, my feet are happy wearing them for a day of running errands, walking the mall, or a few blocks into town.

I don't care about the crew socks trend; I wear no-show socks with skirts (my favorite no-show socks, and a great no-show sock hack), and with jeans and pants, I wear fun socks. I've bought a lot of striped socks this season (these are fun, these are wool but not thick or itchy, love these too) and wear them so they peek out when I cross my legs.

I got my Veja Volley O.T. sneakers at Nordstrom for $145. There is more than one Veja Volley style; the one I have is $145, not $160. I found the same color and price at Maison Rogue and END. Clothing, neither place I have ever shopped before. The same price and style but in brown was found at Revolve and Bergdorf Goodman. I found a white version with the same name and price at Anthropologie and the same price with white and black options at Bloomingdale's.

The Nicer Than Sneaker But Just as Comfy

I bought a pair of these Vionic loafers this past spring and was thrilled with the comfort and support. Available in medium and wide widths and a bunch of colors, this is the shoe I wear when a sneaker isn't quite right, but I'm not feeling a structured boot or shoe. Super soft leather right from the bat, no break-in time needed, these have removable insoles so you can do my no-sock hack, though they also look cute with a fun “pop” sock.

I have them in cream, but I am tempted to get them in Vintage Blue Haze (I like the matching sole, it's fun), or maybe the Scarab (dark green suede with white sole) or Red (a tomato red suede with white sole). These are nice enough to wear with your work trousers and the Black Suede version has black soles, making them look even more professional.

I got mine at Nordstrom, where they are $129.95. Zappos has them for $130 as does the Vionic site, and these two retailers have the best selection of colors and finishes. DSW has them for $129.96, and Amazon has some options up to 50% off, but the sizes and colors are more limited.

The Reasonably Comfortable Dressy Heels

As mentioned, I occasionally like a heeled shoe, but these days my heels aren't terribly high, are often balanced with a subtle platform, and they have a block heel for more stability and weight distribution. This summer I got the Aerosoles Cosmos sandal in silver chrome and they have become a favorite.

I found them a hair too narrow, even in wide widths, so I used these shoe stretchers, increasing tension over a week which did the trick without hurting the shoe. The wide straps and block heels don't look summer, and even look on trend with hosiery. I wear with suits, with dresses, and they look very hip even though they are from a “comfort shoe” brand.

The Aerosoles Cosmos sandal is available in two with and a bunch of colors and textures on the Aerosoles site, DSW, and Nordstrom for $99.99, Zappos and Macy's for $94.50, and Amazon at a range of prices based on color, starting around $70.

The Elegant and Professional Loafer

I have been intrigued by Sole Bliss for a while. Touted as a luxury shoe brand for wide widths and bunions, Sole Bliss shoes have been seen on celebrities like Drew Barrymore, Helen Mirren, Gayle King, and Julia Roberts.

I wanted a loafer that was a bit more refined than my Vionic pair, something that I could wear to speak at conferences, attend networking events, and look cute peeking out of my pantsuits. Loafers are having a moment this winter, and I wanted a pair that like my Vejas, were a pop of color so unexpected, they go with everything. I bought the Sole Bliss Trinity Loafer in Lime Suede.

These are beautiful shoes and quite roomy. However, they do need a break-in period. The shoes are stiff and structured, and they run a bit high in the back (they could rub on your Achilles, depending on your foot and ankle shape). These shoes are $299 in some colors, and others on sale for $199. If you have wide feet or bunions and are sick of frumpy shoe options, check out Sole Bliss. While I am not in LOVE with these shoes, I like them so much I plan to buy another pair from this brand in the future.

The Flat for Cocktail Pantsuits

I talk often about why you need a cocktail pantsuit, and how they work so well with smoking slippers and flats and oxfords and some styles of loafers, yet I personally didn't own a pair that worked. I wanted something that looked dressy, had a pointed or elongated toe to peek out from the pant leg and look dressy, and have some sort of detail or hardware to make them look fun and stylish.

I tried these on a whim; the black fabric looked kinda weird online and I didn't know if I was a “shoe bow” kind of person. But they are pretty fantastic. They look dressy and stylish, and don't cramp my feet. I added these insoles to help with sweat and sliding, though I think they'd look chic with sheer hosiery like these or these.

The Naturalizer Havana Bow flat is available in four colors and two widths at the Naturalizer site for $130, Zappos for $129.99, DSW for $129.95, and Amazon, Macy's, and Nordstrom for $91.

The Versatile Black Leather Ankle Boot

Trends change, pant and denim silhouettes change, but for two decades I've been glad to have a pair of versatile black leather ankle boots in my closet. Something that looks elevated but is walkable, can be polished and reheeled and resoled at the end of the season, can be worn with a pantsuit, a pair of jeans, a fun pair of pants, faux leather jeans, even a midi- or maxi-length dress or skirt.

This is a shoe I recommend buying the best quality you can afford. If you keep them maintained, you can be rocking them for a decade or longer.

I bought my versatile black leather ankle boot a couple of years ago; it's soft black leather that can be polished up, has a subtle wedge heel and an elongated pointed toe. I like them so much I also got them in alabaster. They're from Naturalizer and no longer available, so here are the ones I would consider if I didn't already own them:

• Poppy Barley “Toujours” Boot: A stylish but not-too-high heel, smooth leather, a shaft high enough to hide under ankle-length pants and longer skirts, available in wide width, and from an ethical company. Use code Wardrobe-Oxygen-Fall-10 for 10% off your order of $100+.
• ALLY NYC Lower Block Ankle Boot: Spoiler alert, I own these in camel and they're gorgeous and comfortable and come in three widths and sizes 4.5-12. This company is woman-owned with an Asian owner, Latina designer, and Black podiatrist to ensure style and comfort. Use code WO2 for 10% off your order.
• Margaux “Simone” Boot: It's surprisingly hard to find an elegant boot that has a low to no heel, but Margaux made it happen with this boot. I own other shoes from Margaux and am impressed with the quality and also with the company's customer service. Available in three widths and sizes 3-14.
• Vince “Rockville” Bootie: I like the elongated modern toebox, the stylish yet low heel, and the reviews that this boot is soft leather and comfortable.
• Ros Hommerson “Elsie” Boot: Ros Hommerson is my go-to for truly comfortable all-day footwear, even with heels. These would be perfect travel boots, offering classic style, luxe leather, and plenty of support and cushioning. Sizes 6-13 with four widths, and use code OXYGEN10 for 10% off your order.
• Naturalizer “Deesha” Bootie: I love the sculptural heel and sleek style. I have luck wit Naturalizer booties and appreciate these come in regular and wide widths. These are also a nice price (currently under $120).
• Michael Kors “Cosmo” Bootie: Under $175, super sleek and elegant, this is a boot I would have worn 20 years ago and wear now and both times would feel very on trend. Appreciate the low slim heel and how these are free of adornment.
• Lauren Ralph Lauren “Willa” Bootie: Classic, chic, elegant, timeless, and currently on sale for less than $125.

The Non-black Versatile Ankle Boot

I have always been a person who has had black as her base color. Black boots and dress shoes, black bag and belt… they always match and the color never goes out of style. But this season with so much cognac and camel and brown leather, I wanted a boot in a warm neutral that would look on trend now, but also look stylish for years from now.

I have had a lot of success with the comfort and high quality of shoes from ALLY NYC; see my review of ALLY Forever Flats which are shoes still in my closet and worn often in spring and early fall. Knowing how well they fit, the quality, and how I know they'll still look stylish a decade from now, I got the ALLY NYC ankle boot with the lower block heel (there is a higher heel version, too). All the colors are great but I chose camel and LOVE them.

There is enough contrast to wear these boots with black or brown, they look so chic with jeans, but also with my cream corduroy jeans, my gray wool trousers, my wine red pantsuit, my black cupro wide-leg pants. And code WO2 will get you 10% off your purchase!

The Winter Boots

Another shoe I have had for so long and is no longer available… the winter boot. In 2016, I bought a pair of Merrell boots with shearling lining and Arctic Grip soles that would give traction even on black ice. I still wear these every winter and love every aspect of them.

They are all black so they don't look so outdoorsy if I am wearing them running errands or when I was on my work commute. The soles really have given me confidence and grip in the winter (I broke my arm in 2014 due to black ice), and they're so simple of a look they are timeless. If I didn't already own them, I would be considering these:

• Sole Bliss “Wonder”: These look amazing. Roomy toebox for bunions or wide feet, shearling lining, ability to fold down or have a higher shaft, zipper instead of laces, and a really innovative sole that has cleats/grippers you can flip to use when outside and retract when indoors.
• Merrell Siren 4 Thermo Mid Zip Waterproof: Vibram® Icetrek outsole, SOLARCORE® Aerogel insole provides underfoot superior warmth while being extremely flexible and ultra-thin, waterproof leather exterior, and a timeless look that won't feel dated years from now.
• Merrell Women's Antora 3 Thermo Mid Zip Waterproof Snow Boot: Vibram Icetrek outsole, Primaloft insulation, and a waterproof membrane.
• L.L.Bean Storm Chaser Boots: Vibram Artic Grip traction, cushioned EVA midsole, 200-gram PrimaLoft® polyester insulation, Waterproof leather upper with TEK2.5® waterproof membrane.
• Merrell Coldpack 3 Thermo Mid Zip Waterproof Boots: Waterproof full-grain leather uppers, SOLARCORE® Aerogel insoles, removable footbeds, Vibram® Arctic Grip™ All Terrain and XS Trek Evo outsoles, zipper closure.

The Indoor Slipper Shoe

On Threads, I asked folks what they wear in the winter at home in place of Birkenstock Arizonas and almost everyone said the Birkenstock Zermatt Slipper. The same support, but in a cozy closed-toe option. I haven't bought a pair yet, I can't decide on color and I won't need them until closer to the end of the year. What color do you think I should get?

The Zermatt shearling-lined slipper is at DSW for $99.96, Nordstrom and Zappos and REI for $99.95, and Anthro has a similar one in tweed or a different red for $100.

The Knee-High Dress Boot

It may feel like knee-high boots go in and out of fashion, but every single winter since 2006 when I bought my black leather knee-high dress boots, I've worn them. Not too high of a heel, smooth leather, a sleek toebox, and room for a slim supportive insole (love these), I have worn them under dresses and skirts, over jeggings and leggings, with short dresses and bare legs or tights.

As the temps drop, it's nice to have a tall boot to keep you warm and protected. Buy a quality pair, polish them and get them reheeled and resoled and update the insoles, and they can last you for decades. I have very wide calves and am in need of a boot replacement as mine are starting to crumble from the inside out. The ones I have been admiring:

• Ros Hommerson “WC MIX” 
• Dolce Vita “Gyra”
• DUO Boots “Dalia Petite”
• Poppy Barley “The Toujours Tall Boot”
• Seychelles “Rose”
• Journee Collection “Tullip”
• Vince Camuto “Avriah”

The Fitness Shoe

When it gets cold, my primary forms of fitness are indoor machines (I have a Hydrow rowing machine) and walking. With my rower, I just wear my old high-top Chucks. But for walking outside, I want enough cushioning to keep me a bit protected from the cold concrete and support to prevent pronation.

The best-fitting sneakers for my feet are New Balance and Adidas, and at the end of this summer, I got the New Balance Fresh Foam X 1080v13 in Limelight. They feel kind of like HOKAs with that bouncy sole and the color goes with all the chartreuse winter gear I got last year from Athleta.

In Summary…

I'll be honest, these aren't all the shoes in my closet. However, these are the ones I wear regularly and know I will wear over and over through winter and into spring. My winter shoe wardrobe may be much larger than many of yours. My job is about fashion and style, so I have a more varied wardrobe and prioritize it over many other things.

I don't live in the same climate as all, and don't have the same lifestyle as all. But I hope my collection can give you some inspiration of what may be stylish and practical and remind you that those really adorable shoes that go with nothing should not be added to your cart.

Buy less, buy the best quality you can find, stick to a primary neutral and have your shoes work with that so you can achieve big style with a smaller closet.

Have you done any recent shoe shopping for the cold? Do share your favorites in the comments below!