Written by Sasha

(Lainey: I have been forwarding all your mail to Sasha – thank you so much for the messages! The style questions have been awesome, and the lifestyle/sex/relationships ones have been really insightful too. We’ll be separating those ones from the fashion articles and posting those soon. We are very, very humbled and grateful that you’re sharing your personal stories with us. Keep sending!)

Hi Sasha,

I have a question about how to wear socks and shoes…strange I know but let me explain. I live in the San Francisco Bay Area, so in the winter it’s cool enough that you can’t always go sockless (i.e. sandals or flip flops like the rest of the year), but I also don’t want to wear boots every day. So if I want to wear shoes, say for instance ballet flats or any other slip on shoe, what do I do about socks? Can you wear socks with slip ons? I think not but then am limited to only boots all winter. What do you think? Thanks, Sarah


When I think of shoes and socks the only thing that pops into my mind is old Chinese ladies walking around in their gigantic athletic flip flops with their paper thin socks. You’ve seen this right? I don’t know what it is about the Chinese but they really dun’ give a sh-t about their loungewear. I also don’t get why grown Chinese men like to ride children’s bmx’s to do errands.

But I digress.

Sarah this is a really good question because the sock and shoe pairing is definitely a thing right now—it was all over the runways for fall and spring. And it’s definitely one of those trends that can go from runway to real-way.

But first off, the shoe has to be a bit special for this to look good. And by ‘special’ I mean don’t you dare do it with a croc or anything that looks like it. It’s gotta be cute because this look is all about the cute. Do I think you can do this with a ballet flat? Not so much. Do I think you can do it with a brogue, a utilitarian flat boot, a high heel, or even a cute Bensimon runner? Yes.

Now onto what you do with the sock. I’ve seen quite a few women hiking theirs all the way up to their knees or even over their pants. If you’ve got the fashion bravado to do this, be my guest. Otherwise find yourself a finer fabric sock and just give them a mild scrunch but please refrain from an elementary school fold.

The outfit also plays a very big part in this because you really don’t want to tip into granola munching territory. So pretty it up and play around with dresses and skirts and if you plan to wear pants or jeans make sure they’re cropped.

Knock your socks off (I’m sorry, I had to) and make sure they match.

I've been out of the game for a couple of years now, I have an 11 month old daughter. And yes, that means I'm back to work in 1 month. I'm also starting a new position and I want to look good, after not really looking too good for a long time. Problem is, I'm at a loss on how to dress my new body - some things will never be the same! I think I'm lucky though, because it seems like tops are longer and looser these days, and I THINK I can do the skinny bottom thing, looking forward to buying boots for it!

I have a limited "parental leave" budget, what are some new modern stylish staples that I need for office wear in Toronto (with casual Fridays woo-hoo). Also keep in mind that I haven't bought anything but "bootcut" and v-neck sweaters for the last decade. Thanks! Emma

Hi Emma,

New mom bod--I hear about it all the time but still don’t know what it really looks like but I’m terrified to find out when I finally decide to procreate.

I’ve received a couple mommy emails (shout out to Sara & Laura—this applies to you too) and the biggest gripe is trying to find something easy to put on in the mornings because lord knows you have sh-t to do. So here are some staples that you should start looking out for.

The dress is always life saver when you’re having a major clothing crisis in the morning. Check out the Bay, French Connection or even Sears’ line Attitude (yes, Sears is getting great buzz – click here to see) for a simple black dress--it will save your life when your kid just barfed on the floor. Put on some black opaque tights and a wedged heel and you’ll be good to go. If you do a kitten heel, we can never talk again.

And yes as you pointed out, longer and looser tops are still the silhouette of choice. So go the Gap, Jacob, Bedo and Joe Fresh and find some simple tops in either a jersey or a silk blend –pick up darker colors like a heather grey, black, and navy. And show off those milk jugs! It’s really easy to get good quality scoops and v necks and you can find them on the cheap so you won’t be pissed when your kid decides to barf on you instead of the floor.

Also think about buying an animal print knit. I’m not talking hooker animal print; I’m talking something a bit more subtle. Line Knitwear has a really great grey and purple animal printed cardigan (click here to see) and Aritzia has a soft coloured printed sweater that will look great with a pair of black jeans or pants. It will give the impression that you’ve read an InStyle magazine in the last year.

A classic white blouse is a staple every season so here’s where you could stand to invest a little. Theory and Pink Tartan are some great labels that know how to tailor. And if you lean more to the girlie side of things pick up a slightly ruffled one. Banana Republic and Zara always have a good sale rack of them. Throw a cardigan over it or dig out one of those v-neck sweaters and toss it on over the blouse.

Also blazers and long chunky cardigans/wraps are going to be your friend. It always looks like you put in some effort and you can literally wear the same top underneath all week long and no one will pick up on this laziness.

And I know you’ve heard it before but the most affordable and most effective way to update your look is going the accessory route. So look out for a few fun printed billowy scarves, go to Aldo and pick up some earrings, and then go vintage hunting and find some great necklaces and rings. I’m always surprised at what some good accessorizing can do to a boring outfit.

Hope this helps with the mental prep of going back to work!

What is the deal with leather pants? I have a pair of black ones, super comfy and am wondering if there is any scenario in which they will still work. They have a slight flare to the leg, so I can't wear them as skinny pants. Thanks,Erin

Erin, NO to the slight flare. Just NO. I want to be more helpful but all I can muster up is NO. I am your friend. I only want the best for you.

Photos from Pascal Le Segretain/Michael Buckner/Gettyimages.com