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.

Pair #1

boot collection 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.

Pair #2

photo 4-11These 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.

Pair #3

Boot Collection 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.

Pair #4

Boot Collection 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.

Pair #5

Boot Collection 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.

Pair #6

Boot Collection 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.

Pair #7

Boot Collection 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.

Pair #8

Boot Collection 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!