Started From The Bottom Now I'm Here: How Drake Inspired The Way I Get Dressed Every Day

The first time I saw the video I laughed. I laughed, a lot. I mean, c'mon, he says the same thing over, and over, and over. He hangs out of a white Bentley as snow falls. Need I say more? I love me some @champagnepapi, it's just this video:


I can't...Or I should say, I couldn't.

Cut to three years later and I'm now using this song for the basis of probably one of my most fundamental posts yet.

I still don't get the video, but the song stuck. Who's laughin' now? Well, not Drizzy. He's probably kind of busy getting ripped and being a mogul and all. But you get the point...



So, this is how I get dressed every, single, day: I start from the bottom of the outfit equation, and now I'm here.

If you think about it, your shoes are the foundation of every outfit, figuratively and literally. They set the tone and can also be one of the best ways to get your own unique sense of style across. You also need them to walk from point A to B.

Here's how I do it every morning:

I open up my closet and look at the shoes in there. Based on the weather outside, I decide between open-toe or closed-toe. In San Francisco, a closed-toe ankle boot is key, but it doesn't mean I go with that option daily. 

Once I know that piece of information, I look at my shoe situation (I'm not at Imelda Marcos levels mind you; I have a lot of shoes but not as many as some would venture to think. You don't need a gigantic shoe closet for this to work, you just need your shoe game to be in check), and see what pair of shoes will fit.

The inside of my brain sounds a little something like this:

"The black ankle boot maybe? Nah, that heel starts to bug me by the end of the day. Maybe I'll go with the neutral ankle boot from Splendid and then I can wear my J.Brands...But then what top do I want to wear because those are high-waisted flare legs. Oh, I know, I'll go with the camel pump and a skinny leg jean. Yea, no need for the extra fabric at the hem. It's Monday, I want easy. Ohhh, plus those fit loose so they're more comfy and I want to wear that new fitted Reformation top...I need more coffee...Did I pay rent? Oh right, the pumps..."

Once I pick the shoe (in this scenario my go-to classic camel pumps) I can start on what pants (or in my case, jeans as I wear them about 99% of the time because I can, but this theory still applies if you can go with denim in the workplace or not) will work.

Now that I know which shoe I'm going with, I know where I want the hem to hit. Again, I picked neutral pumps so I could go with a long pant/jean or skinny pant/jean. Both work. 

I wanted to keep it simple so I picked my favorite pair of skinny leg jeans that hit (and fray, so fun) at the ankle. The focus will be on that hem because the shoes are neutral. Perfect. 

Next, I figure out what top I'm feeling for the day that also works with those jeans. And so on, and so on. Got it? It all, starts, with, the, shoe.


Image source:

Here are a few examples because pictures are always more fun:

1. If it were me, I wouldn't opt for a flat shoe and a jean that hit that far above the ankle. I mean, it's Karlie Kloss, but she is a super model and has super model proportions. I, on the other hand, would pair this jean with a neutral color pump (or even the plum color) and go. 

2. Ok, in this case, there's no way I'm cuffing the jean so that it hits right at the top of an ankle boot. Again, you have to go with what feels right to you and also fits your body type (learn more here). If I knew I were going to wear a cuffed jean that hit at the top of my ankle, or even if this was a classic black ponte pant that hit at the same height, I would go with an ankle boot in a neutral color that didn't cut off the vertical leg line or, go with a black ankle strap sandal. Or, you could always work a classic black d'orsay pump into the equation. 

*Click the links if you want a 'visual' on the products I mention. Sometimes it's easier with pictures, I totally get it.

3. For this casual look, I would make sure I went with a pant that didn't drag on the ground with that low oxford heel, and also a pant or jean that extended below the ankle. I know this isn't rocket science, but clients have told me, 'oh, I didn't think of that,' often enough for me to learn that sometimes my most automatic thoughts can be something new and different to others learning how to put looks together. So, automatic thoughts, here you go...Knowing me and my style, I'd add a higher heel to this.

I would either go with my new Splendid ankle boots in a beige/olive color or opt for a mid-calf riding boot with a heel. If you feel daring, this would be a good outfit for an over-the-knee boot (if you have the height; if not, make sure that t-shirt hits below the hem of the jacket to create the illusion of a longer waist; I do it all, the, time). If you've been binge-watching Jessica Jones like I have, you could also go with a tougher motorcycle boot

4.  So for this look, if I'm getting dressed in the morning and feel like wearing those stacked heel sandals, I would want to show them off and go with a pant that cuts off at the ankle. In this case, she rolled the cuff to get the job done. These would also work well back to a skinny black pant. Then as I moved up in the outfit, I would make sure I added in layers to keep me cozy and counteract that open-toe action. An ankle boot would feel too bulky and normally I wouldn't go with a flat because I trip in them all the time, but again, it is totally up to you, your proportions, and let's be honest, your mood that day.


5. Gahhhh, I adore all things Burberry. I love this look, I love the coat, I love the pant, I love, I love, I will stop now...Ok so the shoe really doesn't matter. She could be wearing hideous lucite platform pumps with goldfish swimming in the heels for all I care.

When I'm in the mood to wear a classic high heel (pump or sandal) I will opt for one of my longer, flare leg jeans similar to these pants. All I'm looking for is height, and a slight platform at the toe will help with comfort. A high boot works too as long at it doesn't go too far up the leg and leave a line (all depends on the fabric of the pant; on a thick denim that won't be an issue). I will say that a pointed toe sometimes help extend the eye line here so if you want to look even more Amazonian, give it a try.


So there you have it...I start from the bottom and complete the look from there.

There are so many factors that come into the equation on the rest of the look (i.e. Is it cold out? Do I feel like getting dressy today? Am I walking around the city all day? Am I having a good hair day? The list is endless) so I try to give myself a clear starting point, something I can build on.

I find that this one change has made getting dressed in the morning considerably less dramatic for me. 

You can do it too, or at the very least, try it out. Start at the bottom and finish strong.

Simplify your life a bit. It starts with your closet oddly enough. And...


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Check Me Out in the January Issue of Real Simple! Gahhhh!

It is relatively impossible for me to express how cool it was to wake up this Sunday, stumble into the kitchen to get my coffee, and see the latest issue of Real Simple waiting for me on the counter.

The real dream-come-true scenario peaked when I flipped through the pages to find my name and quotes from my mouth woven into the latest feature on closet organization and decluttering. It was a big moment for me, IS a big moment for me.  

I break it all down in detail within the pages of my Closet Organization: The Crash Course, but there was something about being able to talk through those closet "theories" with the brilliant editor writing this piece, that had an unexpected, yet entirely welcome, effect on me.

As the words spilled out of my mouth on that call a few months ago, I remembered why I started this business in the first place. And for that realization, or re-ignition really, I am profoundly grateful. It lit a fire: 

The Bye Bye Closet Hang Tags are officially launched, and let's just say that book #3 is no longer just a thought in my mind, it's happening and it will be the most personal one yet...Sometimes all it takes is one epic conversation to breathe new life into your everyday and shift your perspective. 

So, if you haven't already, go pick up the January 2016 issue today!

Holiday travel time is upon us and I can tell you, this is perfect plane-reading material people.

Check out a preview below and thanks again to the amazing team at Real Simple. I'm SO happy to grace your pages:

A little closet organization inspiration...

It never hurts to get a good visual on where your closet could be right? Sometimes it's the perfect motivation when you need to jumpstart your wardrobe just in time for the holiday party circuit. Here we go: