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When the first cold day arrives in early November, I’m downright delighted to pull out my cozy sweaters and slip on some heftier boots. Fast-forward two or three months and I’m bored to tears with my entire wardrobe—and there’s still quite some time until I can start wearing my spring pieces. But I’ve already sunk my funds into ski trips and new furniture for the living room. So what’s a girl to do? Not max out a credit card, that’s for sure!

Instead, I’ve started dedicating time to discovering the depths of my closet, and I’m now challenging myself to wear new outfit combinations I haven’t tried before. Through my sartorial boredom, I’ve found that these four steps work best when it comes to revamping your style without spending a single cent.

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dena wears fun leopard clothes
Dena Silver

1. Reorganize Your Closet and Drawers

When’s the last time you did a deep clean of every single piece of clothing you own? (And sorry, swapping out your seasonal wardrobe twice a year does not count.) I’m talking about taking every dress out of the closet and removing every T-shirt from its drawer.

Sure, this deep clean will be therapeutic to some, but that’s not the point. The real purpose is to inventory what you currently have, because there’s absolutely no reason I should still be holding on to that Bebe tube top from college. My personal rule is to toss anything that hasn’t been worn in the past two years—but I tend to hold on to anything that is sentimental or might come back into style in a few years. Figure out your own personal boundaries for tossing versus keeping and stick to it throughout this entire organizational process.

Once I take all the pieces out of my closet, I make sure to put away the keepers strategically. My tip is to sort items by category and then by color. This will look different for everyone, as we all have different closets, but my tiny closet is split in half, so on the right side, I start with sleeveless shirts, then short-sleeve shirts, then long-sleeve shirts, followed by dresses based on the same three categories. After that comes skirts, sorted from short to long, and pants, also by length. On the left side of the closet, I put blazers and other light jackets closest to the middle and put heavier coats and puffers toward the back of the rack. 

Once my closet is done, I do the same with my dresser. I tend to organize my drawers based on use, followed by color. For example, my favorite black leggings (all four pairs) are sitting in the front of their drawer, while the stack of pink leggings (ranging from baby to hot) are at the back.

What did I learn from the first time I did a deep closet clean? Well, I was very excited about my newly neat room. I also conveniently realized that I’ve acquired eight perfectly great white button-downs, even though I hardly ever wear this style. It also showed me that I’ve got summer dresses on lock, but I’m lacking in the long-sleeve dress department and I could definitely start investing in trousers instead of a new pair of jeans. 

Now that you’ve got a handle on what exactly your wardrobe is composed of, make a list of the items you want to wear more and where you’d wear them. I totally forgot about that blingy gold dress that’s just asking to be worn to a party, and I promised myself I will figure out a way to wear more white button-downs, like layering them under cashmere sweaters.

2. Try on the Pieces You Haven’t Worn in a While

While going through your clothes, take some time to do a fashion show...for yourself. Whether it’s the cold-shoulder blouse you bought a year ago and wore once or the leather skirt that feels too va-va-voom for most events, you might find the once lackluster piece actually fits better now or goes with a piece you’ve since acquired. Do this with the pieces you’re planning to give away too.

But rather than just trying things on for size, see if you can build a proper outfit with each piece. Go on, add shoes, a bag or other accessories to truly complete your look. If the outfit feels comfortable and like something you’d wear, then snap a picture.

dena triptych
Dena Silver

3. Reference Your Old Photos

Whenever I wake up on a weekday without a single idea of what to wear, my gut reaction is to browse Instagram...for an hour. That usually results in my being late for work and out $300 because I splurged on a blazer that looked so good on a Danish influencer who’s 5'10" (I’m 5'2"). In order to save myself funds and precious morning time, I’ve started browsing through photos of myself—specifically, outfits I’ve previously worn. 

I now keep a folder in my phone with looks I’ve worn and liked in the past, like a mirror selfie from an average Tuesday or a glam shot from the office holiday party. Some of the getups are so classic that I’ve easily replicated them for years, while some of the bolder choices are saved for the moments when I’m feeling more adventurous.

And while I might not wear the exact same skirt and tank combo that I did in 2016, I might remember that I still own the ribbed top and that it will pair perfectly with some newer leather pants.

dena wears fun clothes
Dena Silver

4. Try Unexpected Pairings

Love your snakeskin-print jacket but not quite sure how to wear it to the office? Or maybe you’re just feeling tired of the blue jeans you wear every third day? Wondering if you could wear that black dress one more time before dying of embarrassment?

The quick fix here is to try on pairings you’ve never tried before—and that you would never think to put together.

For example, try the snakeskin jacket with a black turtleneck, play around with shoe and belt pairings to spice up your blue jeans and consider layering a sweater over that black dress so it now looks like a skirt. As my mom always told me, “You never know what it will look like until you try it on.” (I regret to inform you that she was absolutely right.) What might look absolutely insane lying flat on your bed could look completely different on your body.

But don’t get too out-there with your pairings, because they have to be wearable after all. And now you’ve got a ton of new outfit options, without even a single swipe on your credit card. I recently rediscovered the light-gray cashmere turtleneck I wore every other day last year, and after it came back from a trip to the dry cleaners, I knew I wanted to wear it to work. But not with jeans. So I tried it with one of my favorite summer slip skirts that features a super delicate lavender pattern on a cream silk. And then I slipped into a pair of caramel-colored western boots. It totally sounds like it wouldn’t work, right? Well, it does and it’s one of my new favorite things to wear to work. 

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