I love the cold weather for one reason, boots! Yes, I may be suffering from a serious lack of Vitamin D and I loathe the fact that it gets dark by like lunchtime, but, boots, I love them. I don’t think I wear anything but boots once the cold weather arrives.
In today’s accessorizing post, I want to talk about building a functional and stylish boot collection by welcoming you again into my wardrobe. Below are all the boots I own, along with my tips on how to figure out which types of boots you need. Just like my jewelry, I am very discerning when it comes to buying boots. I don’t like to have duplicates of what I already own, and once I have a pair of boots that play a certain function I don’t buy anymore. Being this conscientious really helps with shopping as it can get so incredibly easy to get swept up by all the pretty shoe styles. Before you set out shopping check out all my tips below.
How to Build a Functional and Stylish Boot Collection
Geography The first and most important thing you need to consider is geography. I live in the northeast, it gets cold here, and if this winter is anything like last year it is going to be like North Pole cold. Not only do I need to think about stylish boots, but I need to think about covering all bases. I am a New Yorker, my mode of transportation is my feet. I don’t just get into a car to travel from point a. to point b., I walk. I need to think about being covered in boots for inclement weather.
Look at your own life and use this to be really practical in your approach to buying boots. If you live somewhere warmer it’s not likely you’ll be putting your money towards a pair of snow boots. Geography is an important factor in figuring out what you need. It may not be fun to have to pull back, but you will appreciate it later when you actually wear what you own.
Lifestyle Do you spend a lot of time on your feet? Are your evenings spent going out to fancy places? Do you have kids, do you work from home, do you work in a conservative office environment? These are all things that are crucial to consider when buying boots. I have swooned over a pair of 4″ suede stiletto boots but have put them back after reminding myself that I spend a ton of time on my feet and that my lifestyle is way more casual than the boots I am considering calls for.
It can be hard to not “wishful wardrobe”, which means to buy clothing for the lifestyle you wish you had vs. the one you actually live. However, it’s even harder to stare at a pair of boots in the closet with nowhere to wear them. Boots can be expensive, save your money for the pairs you will wear.
Personal Style Lastly, personal style. Not only do you have to consider your personal style and what you are drawn to when it comes to boots, but you have to look at your style on a whole. Are you drawn to booties but really don’t have the personal style that warrants owning them? Many times we can find ourselves drawn to shoes but we don’t have the wardrobe to make them work. When you pick up a pair of shoes, be clear with yourself on what in your existing wardrobe would work with the boots you are considering.
My boot collection
Below are photos of all the boots I own, with the exception of my trusty UGG boots in chestnut and my Hunter rain boots. It is important to remind you that I don’t wear black, so I don’t own black boots. What is also important to point out is that what makes practical sense for me to own may not make sense for you. However, as I explain the rationale behind each pair I own, my hope is that you will start to figure out better ways to identify your own needs.
I’d seriously be lost without a pair of cognac riding boots in my wardrobe. I have had a steady pair in my closet for at least five years. This is my second pair from Sam Edelman, the Penny style in Whiskey, that I bought last season after I spilled salad dressing all over my previous pair and ruined them. It’s okay, they were on their way out the door.
I always own a pair like this for a few reason. First, they are flat, which is important to me. Second, color-wise, they work with my warm based wardrobe. Third, I like the versatility of them and wear them with jeans, skirts and dresses. I also like that if I am wearing a pair of black leggings (yes, I do happen to own black leggings) cognac doesn’t just work with warm, autumnal shades, but it adds a richness to black. I should also point out that these boots have a generous shaft. They zipped right up my ample calves with room to spare.
These boots from Steve Madden (I wish you could still get them because they are fabulous), are one of my favorite pairs because they really speak to my edgier side. Often, they can work the same ways my riding boots can, but, when I am feeling a bit more casual or want to be a bit more rugged looking, these are what I grab. I would say that I wear this pair and my riding boots the most.
This is another pair I love, from the comfort brand, Naya. Like my boots above, they are more rugged and definitely my style. The reason I have these is because there are times that I want to wear a pair of boots like the cognac Steve Madden pair above, but I want something tall and with a heel. What I also like is that these are brown. These boots are a nice hybrid for me when I want to look dressy but casual.
I will let you in on a little secret about these boots. I got them on Ebay for like $25 at the last minute when I needed to find boots like this that would fit over my large calves. I don’t even know who makes them and I can’t say they are the best quality. However, I have owned them for nearly six years and I still get compliments. They have remained a staple for me because they are much dressier than my boots above, they look gorgeous with brown opaque tights and work for those times where I want a dressier pair of boots but don’t want to wear anything with a stiletto heel.
These are the only booties I currently own. They are by DV by Dolce Vita and I love them more than I wear them. I only wear them with dresses or skirts because I find my body looks ridiculous in them with my very small feet and large thighs when worn with skinny jeans. Last year I found that I grabbed my other boots more often than I did this pair. However, I plan to try wearing them more this winter. This was a good test for me. Before I go out and buy more booties, I am taking note of this observation. Yes, I love booties, but my natural inclination might just be to to grab my boots more often instead.
These grey boot from Naturalizer are like a palette cleanser for me. I think having one pair of grey boots was a great test to see if I really needed more boots in this color. I do wear a lot of grey and these are obviously different enough from the rest of my boots to warrant being a part of my collection. There are some outfits I own where grey would be better than cognac or brown. These boots work.
I have had these brown boots from Corso Como for several years now and, admittedly, I wear them the least. However, I would never part with them. When the need comes for a dressier, more elegant pair of boots, I can count on these. I don’t think I have ever not had a pair of boots like this in my wardrobe. I think they are important, even if they don’t get as much regular use. The leather is also like butter.
If you live in a cold climate, especially if you are frequently outdoors or walk a lot, having a pair of boots, like my trusted Sorel pair, is crucial. I bought these last year and they were the wisest purchases I ever could have made. Sorel boots remind me of Cabbage Patch Kids, so ugly they’re sort of cute. I had to search high and low for olive and cognac pair. I mean, if I was going to be stuck in Sorels most of the winter, they had to be stylish and work with my wardrobe. I love these boots and am SO incredibly grateful for them.
Boots that I am shopping for this fall
Like most women, I am always looking for new shoes. There are definitely some styles I am considering. Below are some styles and the reasons I think they may, or may not, make a good addition to my wardrobe. One thing you can count on is that I will not be buying anything that looks similar to what I already own. The only time I buy similar styles is when a pair I currently own is in need of being replaced.
Flat lace up boots Lately, boots like this have been on my mind. When they first made a comeback I couldn’t wrap my brain around buying them after I lived in them in high school in the 90’s. However, like most things, they started to grow on me. My only reservation with buying them is if they are different enough from what I already own to warrant being purchased. While I have nothing that necessarily looks like them, I do have boots that will function the same as where these lace up boots would. To avoid splitting your wears, it is important to think this way. Even though two boots may look different, they can still wind up playing similar roles, which means that neither pair will get as much use as they could.
Olive booties While I have definitely established that I don’t really wear booties that are more like shooties, I do like booties with a longer shaft, like my Steve Madden pair. I also love olive, especially in suede. I am definitely looking to add this color to my boot collection and think that a more casual rugged style could be a great addition.
Grey heeled boots I only have one pair of grey boots and they are flat and casual. On my radar screen is a pair of heeled grey boots, preferably in suede. I have to be careful, however, I don’t wear stiletto style boots that often. If I am to purchase, I will probably buy a pair with a stack heel for comfort.
Burgundy booties I don’t wear colorful shoes in the fall and winter like I do in the summer, but I certainly am in love with the idea of burgundy booties, so rich, so luxurious, so…yummy. But do I need them? I don’t know if I will ever truly need burgundy boots, but I definitely have been wanting them. I would probably not go for a style pictured above because, while they are gorgeous, they are incredibly impractical for my life, especially for the price tag. On my radar is a more rugged, lower, stacked heel bootie in burgundy that I can wear with dresses and skirts as well as skinny jeans.
Heeled oxfords Heeled oxfords are technically not boots, but they are the closest thing to shoes I would actually consider for fall. The only way I am liking oxfords for myself is in heeled styles and I really only see myself wearing them with opaque tights and skirts and dresses. What I have to really consider is if I wear enough dresses in the winter to justify the purchase. If I do buy them, they will probably be very similar to the ones above, a muddy brown in a suede; something versatile that goes with my lifestyle and wardrobe.
As you look to buy boots for yourself, I hope showing you my boots and the reasons I own each pair was helpful for you. Any questions about boots or what to look for? Feel free to ask me below!
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Thanks for showing us your boot collection! I’ve been looking for a couple of months now for a low-heeled waterproof boot to wear casually with jeans and trousers. I just received several pairs to try on yesterday and decided to keep these La Canadienne (http://www.zappos.com/la-canadienne-sue) because they are comfy, stylish and very well made. While searching on Zappos I found a pair of bordeaux booties you might like: http://www.zappos.com/rieker-r9170-adora-70. 🙂
You can never go wrong with La Canadienne!! They are great for bad weather and of amazing quality! I am glad you found them. Thanks for sending those boots along! I really like them. Only problem is they have black in them and I probably don’t have anything to wear with them because I have no black in my wardrobe. I think I want a pair in burgundy suede. I just love suede boots in the fall. But thanks for sending! Definitely worth the look!
My eldest dog, Robin Hood, made a snack of my favorite cognac riding boots recently, ones that I’ve had for about 15 years. So, what I’ve done is cut them off (they are unlined) and kept the extra leather for either having them altered into booties or using the extra leather for moto-inspired patches on denim. Meanwhile, I’ve rolled the cuff to expose the suede while I decide. I do have another pair of cognac tall boots but they are slightly cowboy inspired and don’t fit the same role in my wardrobe.
Ugh, my cats love the insteps of my leather shoes. I got int he habit of always storing my shoes in boxes as a result, or keeping them up high. If you want another of cognac boots I can’t recommend the Sam Edelman pair enough. Funny, I got them last year but they are all over the stores this season. Only issue is if you have narrow calves, the shaft is quite wide.
Alas, my calves are like toothpicks
I love your explanations of the roles your boots play! It really helps me understand why I reach for certain pairs more often in my own wardrobe. I love your Steve Madden pair and wonder what search terms you would use to find something similar? I think a pair of burgundy booties would be a very versatile addition. I purchased a pair of Rebecca Minkoff booties in burgundy last year and wear them with everything!
I am so happy to hear this! I am glad it was helpful for you to hear my own thought process. Sometimes I am definitely a little too pragmatic, but I think it is important to be realistic. I’ve never been a ridiculously wealthy person who has had a ton of room for mistake purchases. It’s sort of like people who don’t like wasting food. I’m the same way with clothing.
And, you’re in luck, I have a habit of remembering the styles of shoes I buy. That Steve Madden bootie is the Brewzzer. I would say the closest you can get from SM this season would be the Yale bootie, only it has a heel. http://rstyle.me/n/svsdi8d2e But if you want to do a general search, I think a moto bootie would be your best bet. I hope that helps!
Thank you! This article is exactly what I needed!!! I continue to love your blog so much, it has so much practical information I look forward to each entry as my daily must read. As someone who also doesn’t wear black and needs a professional plus casual wardrobe, but still wants to look stylish your inspirations/outfit combos are perfect.
It gives me nothing but glee and happiness to know that what I write resonates with others! Thank you so much for sharing that comment with me!
I love these posts that explain things by looking in your own closet! Both this and your recent accessories posts have been so useful to me.
I like your “one and done” rule and your explanations of both the boots you own and those that you’re thinking about buying make a lot of sense to me. But as I think about how to apply that to my own closet I wonder how you decide when something is “different enough.” For example I can see how it makes sense to have both brown dressy tall boots that are in your closet and gray dressy tall boots that you’re considering purchasing. Similarly I have a pair of gray tall boots with a casual, riding boot feel and would really like a pair of brown/cognac riding boots. But what’s the line between “these serve a different purpose/go with different outfits” and “buy all the colors”? (I’m not saying you’re on the wrong side of that line, I’m genuinely wondering if there’s a more general principle that can be articulated here.)
Hi Sarah, That’s a great question. I don’t know if I can give an answer that will work for everyone, but I can certainly try. I think there is nothing wrong with having more than one color in a boot classification (classification meaning like riding boots or dressier boots, for example), just as long as that color belongs in your wardrobe and that the color aren’t so close that they can essentially do the same thing. I also think that having a variety can change up an outfit, if that makes sense. For example, I will wear my cognac Steve Madden moto booties or my Naya brown boots with exactly the same thing as I would my cognac boots, but with a boot change the outfit gets a different feel. However, at the same time, I can see that having a brown riding boot and cognac pair would probably get too repetitive because they can probably fill the same need or look I am going for. I don’t know if my answer is confusing things more or helping. If I am not understanding your question clearly enough please feel free to elaborate further!
Thank you, Bridgette! Actually that is really helpful — the combination of “does this color have a place in my wardrobe?” And “will this help me create a different look?” Seems like a good way to gauge the usefulness of a potential purchase. Probably for items other than boots, too….hmmm, I am going to do some thinking about that. Thank you for your thoughtful reply!
I am glad it helped! So much of it is just routine for me in my head so you really made me think. We can’t always be super strict about everything but having guidelines does help with avoiding unnecessary purchases. Any other questions about this feel free to drop me a line.
Your “one and done” rule is a very clear guide to use when contemplating adding something to your wardrobe.
I guess how many items you have in your wardrobe depends on your goals. And maybe where you are on building that part of your wardrobe.
For example I own 2 pairs of boots: 1 knee high dark cool brown riding boots & 1 suede navy 3cm chunky heel booties. I wear my booties more than the riding boots, but will not buy anything similar in colour or style for my 3rd purchase. I prefer a more minimal boot collection and don’t see myself going past 6 pairs even if I had unlimited funds.
To someone else, for their fashion style & lifestyle needs they may have a smaller or larger collection.
Exactly, Ebony! I was thinking about this a few days ago. If I was a corporate women who had a lot of tailored pants in my wardrobe I would probably have a lot more shooties, but my life is really casual and when I do get dressed up I will always grab a dress or skirt first. I don’t even think I own a pair of tailored pants, actually.
I have some clients with very small wardrobes and others who need two closets. There really is no ‘one way’ or pieces that every woman must own. I really laugh when magazines call me for a quote about what “must have pieces a working woman must own”, for example. There really is no single answer to this. Instead, what is important is for a woman to be able to look at her own life, needs and style and figure out what is right for her. All I can really do is make some suggestions and give her tips on how to navigate that.
Am I the only one who sees a brown pair of boots whenever Bridgette posts photos of her grey boots? It’s so weird that they would skew brown in a photo.
I counted and have 9 pair: Rain boots, UGGS, Sorels similar to yours only grey, a fancier pair of Sorels that I love but were made for someone with *really* wide calves, a funky pair of Fluevog riding boots, a more classic pair of Frye riding boots, a pair of tall Keen boots that are great in the rain and on the playground but have no traction in the snow or mud, a pair of burgundy Clarks moto boots that I want buried with me when I die, and the newest, a pair of charcoal grey Clarks Moto boots (same line but slightly different style) that come up mid-calf. I got rid of my kitten heeled Kenneth Cole boots a few years ago and am sorely regretting it, as they were my “fancy” boots. I only wore them once or twice a year, though, so I figured I’d pass them on. Lesson learned… Am now stalking eBay for a new pair..
I had to check the grey on those several times also…
I had to check the grey on those several times also…
Oh, that’s because they are a very warm grey, like a taupey grey.
I find that heel height affects the use for me more than anything. I admit to having too many pairs of boots but I need a few pairs that are flat for when my feet bother me. I just ordered a pair of olive engineer boots and note that they satisfy two of your shopping list items. I also like to have a variety of booties to add interest to outfits but realized that the reason I am not wearing them with skirts/dresses is that they are dark and chop up the leg line too much so I am looking for a taupe bootie for this purpose. I think I need to adopt your strategy as I sit here contemplating my wants vs. needs.
Thanks for a great read and some valuable insight.
You had me at olive engineer boots. I am glad this post helped you!!!
Tsubo is one of my favorite brands! I have a pair of pumps from them. I am always looking for comfort and style and Tsubo definitely falls into that category! And I seriously love the pair you shared!!! Thank you for sending my way!
I really love Corso Como shoes. The boots I have are almost like socks. I have actually worn them barefoot. I can’t say that after a full day my feet are completely comfortable, but the way the leather molds to my feet and legs is like butter!!!
And if I can suggest this, get your Sorels now. Last year I waited until the last minute and it was almost impossible to find a pair I liked. I almost had to settle on a pair of ugly ones that were not in colors I liked. I can’t even remember the website where I found mine, but it was like finding a needle in a haystack. Winter boots are sort of like air conditioners. At the first summer heatwave you can’t find one anywhere. Same is true about the first freezing day, there isn’t a boot to be had…at least a stylish one! Let me know which Sorels you get. Mine are the Tofino and I know the Joan of Arctic style is also very popular.
I absolutely love your blog! I keep checking back for new posts. Your accessory post was amazing. After I read it I looked thru all my jewellery (most of which I never wear) and low and behold all the earrings I’ve been wearing are slight variations on the same idea. Time to shake things up!
I own a similar pair of boots to your #2, but from Zara, in suede, the heel is higher but so comfy, I could wear them every day. I’m from a cold climate too, so I’m surprised that you don’t have on your wish list an alternate style of winter boot. My winter boots are also similar to yours, but a cheaper version by London Fog in caramel brown and olive green, have a pair of leather, fur lined booties too I got last year for dressier cold occasions (rare too, but always looked clunky in my too casual boots vs everyone else). I feel that I need to get another everyday pair with a bit higher heel to wear with longer pants and also because the London Fogs are a distinct color I always look like I’m wearing the same thing every day (it’s that cold here, all your other boots I could only get away with in fall). So I’m looking at a wedge, mid length boot. Just wondering if you’ve thought of adding a new winter boot and what you’d go for?
Bridgette…thank you for your wonderful blog. I look forward to each post! This boot article and your personal accessories post were just excellent! Though my geography and lifestyle are so different (Southern California & retired), I find your professional experience and advice extremely helpful. Please keep up this great work!
I’d not heard of this brand before but when I checked out your link (so pretty!!!) I spotted these (in harvest) to hmmm over 🙂 http://www.6pm.com/tsubo-loe-black?zlfid=192&ref=pd_sims_v_1 I’ll have to see if I can find them in my size.
Hi Bridgette, great post! I have wide calves and am looking for a dressy pair of black boots but have trouble wearing heels due to foot problems. Would you consider wedge boots to be dressy or not?
Thank you Mare! The grey ones are coming for me to try on. 🙂
Brilliant! I hope they are just what you’re looking for!
Oh boots, how we love you so! I have a horrid feeling that I donated my black booties to the charity shop at the end of last winter so now I desperately need a new pair! I’ve also got grey suede and a warm beige bootie plus brown low heeled boots and black riding boots (which I wear several times a week and all weekend…)
Bridgette, another great post. I’m in the Midwest so we are still in boot weather. My problem has been finding boots that aren’t too tall. The Penny’s hit me right on my knees. Ideally I need about a 14 in shaft max. Any Recommendations?