This week, we are pleased to bring you the first installment of what we hope will become a regular segment on this blog: Ask TST! Our inaugural question comes to us via Facebook from our dear friend (and unofficial marketing advisor) Adrienne, who bought some killer kicks and came to us for ideas on how to make the most of them. Read on to see how we responded, and don’t hesitate to drop by and ask us some questions of your own. We live for this shit.



Dear Adrienne,

Hi, it’s me, your “cool friend” Taylor. First of all, these are fucking awesome. As someone who is obsessed with both sneakers and metallics, these are a holy grail shoe, as far as I’m concerned. Second of all, thank you for giving me an excuse to look at clothes on the internet, because I’m broke and have been avoiding even browsing as a result. Since I know you personally, I was armed with some useful information on this mission. Firstly, I know you’re a badass professional lady working in an office environment, but you also recently had foot surgery, which means you can get away with wearing Adidas to the office. Second of all, I know you are a storyteller and performer with lots of cool friends, which means you’re out and about in Chicago of an evening. And third of all, I know you’re a wonderful mom to an amazing seven-year-old son, which means you have a lot of errands to run and children’s birthday parties to attend, so you need something cute but comfortable to zoom around in. So you need three different templates to work with, as well as some options–and lady, I’m here for you.

Let’s start with your working girl ensemble:

Adrienne 1
MANGO blazer
Monki pants
BaubleBar necklaceA cool shoe deserves a cool jacket, and this one is fun while still being totally appropriate for the office. To balance things out, I kept the rest relatively simple–the necklace, although big and chunky, is a simple metallic, and the blouse is as streamlined as it gets. However, I think you could totally also do a blouse with some interesting but understated details like this one by Just Female, or this one by Modcloth. The shoes, although they’re funky for the office, are neutral enough that you could really play around with jacket options, too. Here are some more from Mango. (And, okay, that last one is a bomber jacket and you totally can’t wear it to work, but I still think you should have it.)

Speaking of things you can’t wear to work, next we have a formula you can use for your other job, which is being an acclaimed storyteller, comedian, and writer/producer/star of your own one-woman show:

Adrienne 2

One of my personal favorite combos for going out is a sneaker and distressed jeans with a flowy, dressy shirt. The looser silhouette of the shirt (and the stretch in the Topshop jeans, which are some of my favorites for that very reason) means that you can eat and drink your face off without your clothes feeling too tight and also look relaxed and fancy-free. It’s a win-win. This is a super simple and endlessly variable pattern, which means pretty much any silk or silk-like blouse will do. And I know you like a print, so I found a graphic alternative at (where else?) ASOS. You can also try colors. As mentioned above, I love maroon and gold together, so this embroidered satin shirt would be a great option, too.

Last but not least, we have your errand-running supermom lewk:

Adrienne 3

MANGO sweater

Northmore Denim boyfriend jeans
Adidas Originals tote bag

The essential here is the boyfriend jean, of which there are many different versions. This one is slouchy but still polished, which felt right for a recovering Ann Taylor addict. The sweater is a no-brainer: a cozy sweater is everything, and also Chicago is about to be cold as a witch’s tit. I included this Adidas tote because a) it’s awesome, b) it’s big enough to hold a bunch of crap, and c) I didn’t know Adidas made totes, and for some reason found it funny. (In a good way. I kind of want it for myself.) I also found this sweater, which I think would be a great choice because it’s so aggressively feminine that it sharpens the interest of the more casual pieces and turns this into an intentional Look.

Although I could go on forever, I’m going to end here and hope you feel sufficiently inspired to take these ideas and run with them. Because, as corny as it may sound, the thing that really makes a great outfit is putting your own stamp on it.


Congratulations on your new shoes, babe. I think you’ll be very happy together.


CU Next Tuesday!




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