High Heels and Training Wheels: Closet Building 101: An Easy Step-by-Step Guide to a Wardrobe Overhaul

One year ago, when I made the decision to drag myself out of my "mom wear" of sweats and yoga pants and to start consciously dressing myself, I had to build an entire wardrobe from the ground up. Having literally nothing as a starting point and having to completely break down my closet it to rebuild it back up again was extremely intimidating. Not only could I not afford a wardrobe overhaul, I had no idea where to start. How could I get the most bang out of my buck? How do I know what pieces to buy? Where do I begin??

The big, bad, scary beginning

In the beginning, the task of starting completely fresh seemed to be so big and scary. And, although it took me a while, eventually I learned the whole process could be made easy just by breaking it down and following a few simple steps. The tips and steps themselves are so simplistic and really common sense, but when you're diving headfirst into the unknown and starting something new like this, "simple" can sometimes be elusive. It was for me anyway! I was over-thinking the whole thing and making it so much bigger and complicated than it needed to be. I mean, it's not science, it's just clothes! But I was incredibly disorganized and went about it all in a very haphazard way that left me with a closet that I couldn't do anything with. No bueno!

So the tips I'm sharing today are very basic and really just about how you can simplify this whole process and make it easier on yourself. They may not seem all that insightful to some of you seasoned veterans, but I'm targeting the rest. Yes, you! I wish I had something like this to act as my guide when I began, it would have taken so much intimidation out of, what seemed like, a huge task. So if you've built a wardrobe solely for functionality and now you want to turn it into a wardrobe for function and style, this one's for you. Hopefully I can help take a little bit of the fear out of starting all over again for you because I promise it's not as scary (or expensive) as it seems!

How can this work for you?

If it still sounds like this is more complicated than you're willing to take on, don't worry! This "guide" is for absolutely anyone; any size, any age, any style. I am not breaking down specific items or wardrobe staples that "everyone" should have in their closet or anything like that. Those posts can be really helpful, but we're thinking in broad strokes right now. This is more like a method for determining what you want in your closet. You need a direction, you need to figure out your style and tastes, and you want to stay on budget.

How to upgrade your wardrobe without spending a lot of money

Step 1: Find your Inspiration

First and foremost, you need a direction. The only way to begin is to find out what you like. That might sound unnecessary; you might think you already know what you like. But chances are you don't! If you've spent years without a sense of personal style, or without thinking about what you're wearing, you might surprise yourself at what appeals to you now. And when was the last time you dressed for style anyway? I can guarantee your taste and needs have changed since college; what you liked 10 years ago probably isn't going to work for you now. I mean, I know my flare jeans and platform sandals ain't cuttin' it anymore. Naw mean?

So how's the best way to do this? Go to the mattresses! No, wait, that's the Godfather. I mean, go to Pinterest! Seriously, Pinterest has been my sole source of style inspiration. That might sound silly or over-simple; what's so secret about Pinterest? Nothing. Everyone and their cousin is on Pinterest. Heck, you probably got here from Pinterest! But it's the easiest way to get a sense of your own personal style with what's already mapped out right in front of you. So step 1: spend a day going through Pinterest and pin every single thing you like. And I mean every single thing. Don't worry about "I could never pull that off" or "That would never look good on me". We're going to get to that. Plain and simple, if there is something that appeals to you in any way, maybe it's just the color combination or maybe it's just the shoes; pin it anyway! Don't worry about "trendy" or popular, pin what you like.

This step doesn't necessarily have to be Pinterest specifically, they're not paying me to send you to them or anything, I just like the ease of having everything digital and in one place. If you felt up to it, you could even do a style board and use looks out of magazines or something like that. Whatever floats your boat. The general idea is just to find as much inspiration as you can. But, however you choose to do it, you really don't want to skimp on this step. It is honestly of vital importance if you don't want to be overwhelmed in a store. It's essential for organizing our tastes and likes so we don't find ourselves walking into a packed Old Navy and buying everything we see (because it's 60% off!), only to end up coming home and thinking "Why did I buy this?" or "What the heck am I going to wear this with?". I like to think in terms of "outfits" first and then break them down. It's just the easiest and most efficient way to not end up with a bunch of random "trendy" pieces we can never wear.

Step 2: Divide and Conquer

Now that we have a good base of inspiration to work with, we want to create our Vhen diagram. Nah, I'm kidding. But we are going to start grouping together similarities. Basically we're going to divide all of these pins by grouping like-items onto more specific boards. I have 3 boards; "Fall and Winter Style", "Spring and Summer Style", and a general "Style" board. But it can be really helpful in organizing by getting even more specific and I recommend that you do. It's definitely on my "to-do" list. I can get lost in all my pins every now and again so it'll be easier down the road if you're very specific. Like a whole board filled with just outfits that have skirts in them, or outfits with just stripes, or just muted colors, etc. You want to group your pins in a similar way so you can figure out the common thread between them. What is it that appealed to you out of these looks? Why did you select these particular outfits?

Breaking your inspiration down and grouping it will help you find all that out and get a more specific idea of what your taste and style is. Maybe you notice that you have a lot of pins with stripes, maybe you like a lot of black, maybe you like a certain shape or silhouette, these are all things we want to know because it is going to help steer us in the right direction when we begin rebuilding. We're going to figure out, with our Sherlock-ish deductive reasoning, what styles appeal to you most so we can piece together a cohesive closet that is going to be functional and versatile.

Step 3: The Overhaul

Now's when we're going to start to go through our closet. Is there anything in there that fits into any of your Pinterest outfits? Maybe one of your inspiration groupings were pins that had red coats in them and you just happen to have a red coat stuffed in the back of your closet. Maybe you never wore that red coat because it didn't "go" with anything or you didn't know how to style it. Or maybe it's not necessarily the same exact color, but it's the same shape and style. Well this is perfect! This step is when you're going to find out what pieces you already own that can come into play in your new wardrobe. "Overhaul" does not necessarily mean you have to overhaul everything. In fact, ideally, we want to build off of our existing wardrobe as much as possible. For instance, I had a denim jacket I was given as a gift and I had never worn it. Not even once. But once I went through my pins, I realized a lot of looks I liked had a similar jacket. So instead of tossing it, I kept it to build "copy cat" looks around it from my inspiration outfits.

Step 5: Rebuilding

Ok, now we're getting to the fun part. Now that we know what we can recycle and reuse from our existing closet, we can determine what we still need to add. Back up there a couple steps ago, we categorized our outfit pins by similar looks/items. This is what is going to save you gobs of money. For example, let's say I really loved an outfit that had green jeans. Yes, green jeans. Roll with it. But let's say it was the only look I found with green jeans and I can't recreate any more of my inspiration looks with them. Obviously it's not going to be very economical for me to purchase that particular item because I can't build off of it for anything else. Make sense? Maybe further down the line, once I have a good base built up, I might want to get adventurous and get a pair, but right now I want to know what I can get the most use out of. That's why dividing and being specific before is going to really help out now. We want to take those common threads we found when we were categorizing outfits by similar pieces, and see which ones we came up the most with. A lot of looks with a leopard print scarf in them? Put it on the shopping list. Lots of chambray shirt looks? Add it to the list. And so on, and so on.

When you're starting at the beginning, your list might seem long but don't let that intimidate or discourage you. It has been a year and I am still rebuilding! But that's not to say that I don't already have plenty of combinations I can make out of just the few pieces I added in the beginning. You don't need to run right out and buy it all up at once, just to be able to make something out of your wardrobe. That'd be suuuuuper costly. And unnecessary. So don't think because your list is large, you need to spend a lot to make a difference. You'd be surprised at how many combinations you can create with just a few pieces. Seriously, check out the 30x30 remix and you can see where it's totally doable to make a month of (different) outfits with only 30 basic pieces. My advice is to start with a practical base of classic items and then each season, choose a few more pieces you want to add.

Winter Additions

I just did my winter closet additions so I'm going to share it with you as an example of how I think about what I add to my closet and how I use this system. You can see how I categorized and used my inspiration, how I built off of it, and how I can recreate these looks mixing the old with the new. This can give you an idea of the whole process and how easy it can be.

1. Gingham Button-Up- $18.48

Out of all of my winter pins, I noticed I had quite a few looks with a gingham button up shirt. Obviously that's a bright red "buy me" flag. It makes sense for me to add this, as I know I will get a lot of use out of it. Gingham has long since been on my "to buy" list but it is a perfect example of how you don't need to rush right out and buy everything all at once. For example, I already have the black leggings, the mustard scarf, the black pumps, the green pants, etc. that are in these looks and those staples are obviously necessary to have before I can recreate these. So these were things I started out adding in the beginning of my overhaul; the neutral classic pieces. Now, when I choose to add this gingham shirt further down the line, I can recreate all of these new looks with this single $18 addition.

2. Camel Sweater- $25.62

Now this sweater is a very neutral basic that can be worn many different ways. But as you can see, I had a lot of inspiration pinned with similar sweaters, which also influenced me to get it. I can already see 4 potential ways it can be worn. I already have the riding boots, leggings, a leopard scarf, a chambray shirt, leather shorts, distressed jeans, etc. So this one sweater opened up at least 4 more looks that I can create with just the addition of a single piece. Never mind all the combinations I can put together on my own! A good fitting, neutral sweater is great for any wardrobe and can be worn over and over in completely new ways. Plus, it's a classic piece, not a scary "trendy" piece that you would feel uncomfortable in. And it still serves a warm, functional purpose too; it's not just for style.

3. Wool Shorts- $20.16

Now this item isn't necessarily a staple. In fact, it was somewhat of a splurge. Not in terms of it's cost, but just in that it can't be worn in as many different ways as the others; shorts in winter is definitely more for style than functionality. Especially as I am cold-natured and loathe being cold...we'll see how much use these actually get. But it's an example of adding something adventuresome after you've built a strong base. I want to stick to the method of adding things that are versatile, but I'm reaching the stage in my journey of wanting to play around a bit and push myself. After you've got a good base, you can start branching out and trying new things. I'm finally starting to shop more for fun than just necessity and I gotta say, it's a great stage! :)

4. Plaid Scarf- $7.56

Plaid screams "winter" to me so I knew I wanted to bring some into my closet. And scarves are a great way for you to introduce new prints in a small, subtle way. A lot of people are afraid of prints, but with something small like a scarf or a belt, it doesn't have to feel overpowering. We want to expand our comfort zone but we don't want to feel uncomfortable when we try something new either. My first run-in with a neon I opted for a bold dress and it made me feel like I wanted to hide myself all day. Trying something new should not make you feel like that! Scarves with prints are a great addition to a new closet for this reason. We can dip our toes into a new print, without diving straight in and feeling like we're sticking out like a sore thumb. It's also a easy and inexpensive way to add interest to something simple you already own.

5. Grey Knit Infinity Scarf- $13.00

Like the last scarf, this item adds visual interest and appeal to just about any outfit. Two things I did already have in my "mom" wardrobe were sweaters and jeans. But they always looked boring. Adding a scarf or an accessory like this is an inexpensive way to help stretch what you already own. And adding one in a neutral color like this makes for better versatility and allows it to be worn with many different things. Any boring outfit can be made better with a scarf!

6. Stripe Sweater- $26.88

Now this sweater is something I really should not have waited so long to add to my closet; it should have been in that first run a year ago. I am a huge fan of stripes and a basic stripe sweater/tee/blouse can be the equivalent of, say, a pair of jeans. It's just that versatile and that neutral. My advice is to start somewhere in this realm. It's also another great "non-scary" way of adding a print into your wardrobe. Prints can seem intimidating but a stripe is not. You're still wearing something simple and functional with a sweater/tee/blouse, but it adds a nice pop that turns an outfit from boring to fun and well thought out.

So with the addition of only 6 items for just over $100, I am now able to recreate at least 24 new looks this winter. That is the most important lesson when overhauling your closet; it doesn't necessarily mean overhaul and binge shopping. 24 new looks from only 6 items! Yes, I've already built a good base but I've been operating on this same principle and using these same steps since the beginning. In the beginning you think you need to throw it all out and begin anew, but beginning anew does not mean going out and buying out the entire store. It's just about shopping smart! Find out what you like, what existing pieces you can build on and what multipurpose items you can add. Once you break it down and figure these simple things out, all of the complication melts right out of it. You will still have hits and misses but don't get caught up on them; they're just another way to figure out what works and what doesn't!

All of these inspiration looks were pulled from my Fall/Winter Style board, feel free to browse and pin away!