My Must-Have Shoes for Fall and Winter

In the warmer months I get creative with my shoes. Yellow wedge sandals? Why not? Silver Birkenstocks? An unexpected staple! But come fall and winter, my shoe collection gets far simpler and more utilitarian. This is my current cold weather shoe wardrobe for 2014/2015:


must have shoes fall winter

1. Sneakers. Now that I’m walking almost every morning, my sneakers have become some of my favorite shoes. These aren’t the exact ones I have but a similar style and price to my discontinued and nicely discounted New Balances via 6pm. New Balance fits my chubby feet and short toes.

2. Brown Riding Boots. Pictured are the DUO Santanas, the very boots I have (seen here and here). As a petite woman, I love how these boots are a bit shorter, elongating my leg and ending at a comfortable height. As a woman with large calves, shins, and ankles I love how these boots fit comfortably (you order DUO boots by the centimeter so they’re a great choice for narrow, average, or wide calves and the customer reviews help you narrow down the styles best for your specific leg shape). I wear these over skinny jeans or with tights and skirts or dresses.

3. Black Heeled Booties. For many years I have worn the Cole Haan Air Talia bootie (discontinued, very similar and cheaper option) and while I still have and love (in fact just got back from the cobbler for a reheeling), the round toe looked weird with fuller trousers. I just picked up the ‘Coolen’ from Jessica Simpson and love the pointed toe, sleek heel, and the wider top that is more comfortable with my thicker ankles and shins. I wear under jeans and trousers, but also over skinny jeans and with tights and dresses.

4. Statement Heels. Last winter I picked up a pair of silver pumps from Nine West (no longer available, similar concept) and was surprised by how much wear I got with them. They add some fun to dark jeans, jazz up an LBD, and look cool peeking out of black trousers for an evening out. The closed toe is more comfortable on frigid nights but the pointed toe, high heel, and silver color makes them dressy enough for most affairs on my social calendar.

5. Wedges. A wedge is far easier to wear for long periods of time; these are my go-to when I know I’ll be on my feet but still want a bit of lift. The booties I have are the Nine West ‘Lottie’ which are discontinued (and not as tall as the one pictured), but this one from Anne Klein is similar in style. I wear with black tights and dresses, but have also worn under fuller trousers where the wedge isn’t as prominently on display.

6. Leopard Pumps. I have more than one pair of leopard pumps, but the ones featured are the Nine West ‘Ugogirl’ which are my newest leopard purchase and my current fave. A leopard shoe is extremely versatile and adds interest to an outfit of neutrals (which I often wear in the winter; hello black with more black and maybe a splash of denim). I like that these have a chunkier heel giving me more support, but a pointed toe which elongates my short frame.

7. Stylish Waterproof Boots. SOREL sent me these boots in September (review here) and they’re a great option for folks like me who have all her pants hemmed for heels. These can tuck under trousers or be laced up over skinny jeans and the grippy sole makes me feel more secure on slick DC sidewalks.

8. Casual Winter Boots. I picked these Treton boots up last winter on clearance at 6pm and they’re one of the best winter purchases I have made. Lined with shearling, the boots are super cozy and comfy. The wide opening makes them easy to slip on over thick socks and when still half-asleep letting Cindy out in the morning. I keep these at the backdoor to go to the compost and let out Cindy; slip leggings inside them and my track or snow pants over them for snow shoveling or sledding, and often slip them over skinny jeans to walk Cindy or a quick run to the grocery store or Starbucks. Previously I had a pair of duck boots (RIP), and even earlier (and likely somewhere in my attic or at the bottom of my office closet) I wore Tims.  Winter happens and function trumps fashion when it comes to weather.

9. Classic Black Pumps. I wear these almost year-round with skirts, dresses, and trousers. Come the coldest months I switch out to booties, but these still hold a place in my closet for the occasional client meeting or day wedding.  My personal favorites are MICHAEL Michael Kors ‘Flex’ and Nine West ‘Flax’.

10. Tall Black Boots I actually have two pairs; a black flat riding boot I bought two years ago from DUO Boots (very similar, same retailer), and a sleeker heeled boot with an almond toe that I got at Wide Widths almost a decade ago (same style, same retailer).  I wear riding boots over jeggings, leggings, skinny jeans several days a week come winter.  I use a protective spray on them so they keep me dry and salt doesn’t eat away the finish.  Tall boots are warmer than trousers alone; I usually add warmth with a pair of knee-high wool or cashmere socks (and sometimes a sock liner for extra tootsie insulation).  Heeled boots are worn with tights to make dresses bearable past Thanksgiving.

11. Slippers with a Rubber Sole. My shearling mocs from Lands’ End are what I put on as soon as I get home from work, have at the side of my bed when I go to sleep, and the first thing I put on when I wake. I like having a rubber sole so I can step out to the recycling bin or mailbox but also to not slip and slide on our hardwood floors and stairs. To keep down utility bills, I wear a cap and these slippers all winter long when indoors and these are uber comfortable.

What are your must-have shoes for fall and winter?

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What I Wore: Seeing Spots

Wardrobe Oxygen What I Wore LOFT Leopard Dress Wardrobe Oxygen What I Wore LOFT Spotted Dress Wardrobe Oxygen What I Wore LOFT Abstract Animal Print Mini Dress
Dress: LOFT | Tights: Spanx | Shoes: Jessica Simpson | Bag: HOBO (similar)

I picked this dress up about a month ago and love its easy one-step dressing. The dress is advertised as a mini dress so I went with a Regular Large to have more length. It’s sort of ponte, sort of sweatshirt material and can easily dress up or down and work three seasons of the year. So far I’ve only worn it in this manner – with thick black tights and ankle booties. However I can envision it with a denim jacket over or chambray shirt under it and come spring with boots and bare legs!

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Ask Allie: Best Boots for Plantar Fasciitis

I’ve been searching your web site for info on boots – how to find a good pair that doesn’t hurt when worn all day, for example. We will be moving to northern Michigan (think: SNOW) to retire in a few years, and by that time I would like to have a good pair of boots. But if I’m going to spend extra money for good quality boots, I just want a pair that I will want to wear a lot. What brands do you recommend for problem feet? I have plantar fasciitis and large feet with large big toes, medium width.

When shopping online it’s hard to know what will work before it arrives on your doorstop. That’s why, for unknown brands and styles I stick to companies that have free shipping and liberal return policies:

  • Zappos – Free shipping, and you have 365 days to decide to return (and returns are also free). To try from Zappos, it’s important to wear socks and try them on a clean carpeted floor; they do not take back worn shoes. I’ve been known to order a pair and have them sent to my office and wear them around the workplace which is clean and carpeted. If they go home, there’s a chance that they will get dirty, dog hair, or never gotten around to being returned.
  • Planet Shoes – A great site for eco-friendly, vegan, and USA-made footwear, Planet Shoes has free shipping and free returns on unworn merchandise if sent back within 90 days of purchase.
  • NordstromNordstrom has a stellar shoe department, free shipping, and free returns. While it’s unethical to return clothes you happily wore, it’s nice that with Nordstrom if you get a pair of shoes you think are comfortable but then say wear sightseeing and end up with pain, you can still return them.
  • Online Shoes – While returns cost $7.95, exchanges are free at Online Shoes and they have categories for footwear such as orthotic-friendly and up to 4X wide shoes and healthy-feet brands like Rockport, Dansko, Cobb Hill, and Sofft. It’s a great site if you’re more familiar with a brand and its fit but wish to try a new style in their collection as they have selection and also customer reviews.
  • The Walking CompanyThe Walking Company’s return policy kind of sucks, but if you have a store nearby (and there’s one in Ann Arbor which you mentioned in your email), you can return in stores for free. The Walking Company breaks down book categories by style and brand like other retailers, but also by comfort level with a specific category just for plantar fasciitis.

If you have plantar fasciitis, you want to find a shoe with good arch support, plenty of cushioning, and a shock-absorbing heel. This can be achieved with a shoe brand and style that provides this, or a shoe that has room for an insert to achieve these goals. Brands like Aravon, Dansko, ECCO, Naot, and Orthaheel are highly rated by those with plantar fasciitis, while brands like David Tate, Munro, Cougar, and Cobb Hill are known for being orthotic-friendly and are more likely to have a roomy toebox for your toes. Searching online, these are tall boots I found that are a classic style, well-rated brand, and would work for plantar fasciitis.

keen tyretread boot

KEEN Tyretreat Boot

With KEEN’s metatomical footbed design, this boot cradles the foot, has excellent arch support, a shock-absorbing polyurethane midsole, and still room for orthotics. Reviews say these are as comfortable as a pair of sneakers and roomy in the toes. Made with waterproofed leather, this classic style comes in black, brown, and tan; there’s also a waterproof version in black and tan that has seam-sealed construction and a moisture wicking lining which would be even better for a snowy climate.

naot viento boot

Naot Viento Boot

This is a classic leather riding boot with simple styling that will be fashionable for seasons to come. What makes this and other Naot boots special is the anatomically shaped cork and latex footbed that molds to your unique foot shape with wear. The footbed also features arch support for pronation control, a heel cup for added stability, hallux support to prevent foot slippage, and an elevated footbed center to release pressure in the joints located in the central area of the foot. Naot claims that wearing this boot, you’ll gain better posture, balance and body alignment. Available in black and brown leather, while this boot isn’t waterproofed, some waterproofing spray and regular maintenance can protect them from occasional splashes and interaction with salt.

Cobb Hill Britney Boot

Cobb Hill Britney Boot

Cobb Hill, a New Balance Company, sent me some of their shoes to try earlier this year and I was highly impressed by the comfort and support of their shoes. The Britney has a stability shank embedded into the midsole which supports the arch and helps create a smoother gait; the TR outsole provides traction control while absorbing shock and maintaining stability. Though the Britney does sport some ankle straps and hardware, the look is still classic enough to withstand footwear trends. As with the Viento, I recommend prepping this boot with a waterproofing spray.

naya abira boot

Naya Abira Boot

The Abira is a classic riding boot in buttery leather with a cushioned footbed that massages the foot with every step and a rubber outsole that delivers long-lasting durability on a variety of surfaces. The foot is roomy enough to fit an orthotic, and the style can dress up or down quite nicely. Naya is a brand known for quality and comfort but can often be found on discount sites like 6pm; when researching this post I found the boot almost 50% off in tan on 6pm.

Now I wish to hear from you readers; any suggestions for this reader? Do you deal with plantar fasciitis? If so what shoes and boots have you found that are supportive, comfortable, yet still stylish?

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