Written by Sasha

(Note from Lainey: thank you for all your style/sex/relationship/ questions for Sasha. I’ve been sending them to her! I’ve also been sending her all your comments from yesterday’s Colin Farrell eyef-ck episode. I particularly like the person who told Sash that she totally should have touched his dong. If you have questions for Sasha related to style or anything else, please email me at [email protected]. Now on to this week’s Sasha mailbag.)


Is there such a thing as wearing anxiety? I have a few items in my closet that I wear infrequently because I'm afraid to wreck them. Especially if they are a splurge piece. My biggest problem seems to be with a pair of Belstaff boots that I bought last year and haven't worn yet. I know. For shame! At least I took them out of the cloth bag and they are in the front hall closet now. You know... ready to go... whenever! What can I wear them with? My calves fit them very snugly so there is no chance of tucking in a skinny jean. Can I still wear leggings? It's cold here in northern Ontario.

Here is a photo of the boots.



Hey Rebekah!

Wearing anxiety—I’m glad I’m not the only one. Why are we such idiots? I mean we spend all this money and at least for me, money I don’t actually have, just to let things sit and go out of style. I don’t know about you but I mostly buy stupid things when I’ve decided that I should dress more like a grown up and then the realization kicks in that I still dress like I’m in high school.

Before I clicked on the link I anticipated some really impractical shoes. But damn Rebecca there’s no excuse for your boots to be sitting at home doing jack sh-t. Those are meant to be worn and they’ll actually look way better after they’ve been worn a bit. Get to it.

My advice is yes, you can still wear leggings but don’t just go for those regular thin ones--you know the kind that should be left for the gym or lounging at home. Step it up a notch. Look for ones with mild detailing like some slight ribbing or go with a different fabric like a soft cashmere. I was actually at BCBG this weekend and saw a great selection. Just be sure that you find the right pair so that you’re not rocking a camel toe, ya dig?

Also something you’ll see a lot his season is leather leggings. They’re not for everyone but if you can pull it off--do it. And dare I say jeggings (fuc* can someone come up with another term?) will do the trick too. You don’t have to drop a lot of cash on them but if you can spare extra change, one of my favourite denim lines is Genetic Denim. Their Shane Cigarette jeans are the sh-t.

And if all of this still doesn’t convince you, have one of your friends try them on. Once you get all jealous at how good they look on her, you’ll be glad they’re yours and ready to wear.

Hello Sasha,

I am going to Vegas on Nov 3rd. While there my husband and I are going to re-new our vows under the Welcome to Las Vegas sign at night. Super Corny, but fun! After that, it's off to dinner and who knows what else. It will be our all out splurge night.

I just bought a super cute black jersey 3/4 sleeve short dress. Think the length of the orange dress Gwyneth wore recently. It has a very slight A line to it. There is a peacock feather print on one sleeve that runs down the side and wraps around the bottom of the dress. It sounds a bit crazy but I love it!

So, here's my question. I am fairly tall almost 5"9' and I do have long legs. I thought it would be striking to wear black tights and black ankle boots. People keep telling me to wear strappy sandals and no tights because it's Vegas. I don't think so, right? I'm also considering ankle boots and no tights. I am super pale though. What do you think?

Thanks so much.



Well aren’t you and your long legs going to have such a good time? Bitch. I’m sorry, that was just reflex. I often have bouts of jealousy Tourrettes.

Let’s get straight to it. I agree with your friends.

I’ve got a few questions though: What do these ankle boots look like? Are they closed-toe? Are they high? Do they show foot skin (for lack of a better word)?

Here’s my gut feeling. If said bootie is totally closed off and on the chunky side I say ABORT. More often than not this look comes out looking quite unbalanced and can make your feet look like horse hooves.

However, if you opted for a short tighter dress then I think this look could work because there’s that element of edge. But by the description of your dress it sounds like there’s some flow to it and sounds far too pretty for this type of shoe.

Plus, you’re going to be in Vegas and from what I hear it’s tits and ass 24/7, so if there is any weekend to skank that sh-t up and show some skin, I think this would be the time to do so. Shave your legs, slap on some Jergens self tanner for the next week and go tight-less. And yes, wear the strappy sandals it will make your already long legs look longer. Bitch.

Dear Sasha,

I work in a super casual office, and I’ve gotten really lazy. Really lazy. I wear flats all the time. Frye boots are about as high as I go! I’ve decided its time to step things up -- I want to start wearing heels… daily!! I’m looking for an amazing pair of comfy booties. Nothing too fancy or too high because I want to wear them to work. Can you help a girl out?

xoxo Jen


This is a tough because I don’t have much to work with regarding your personal style but I’ll try my best to get all John Edwards on your ass and tap into what you might be looking for.

This season you’ll find quite a few bootie options. One look that I’m into is the lace up utilitarian boot. During TIFF Lainey stomped around the office in THIS pair --I wanted to rip them off her legs. She wore them with jeans and dresses and looked great. I can’t promise comfort but I think I would’ve heard her complain if they weren’t.

Another trend is the desert inspired boot. They’re not like the ones we used to rock back in the 80’s. This updated version is way better looking and to be honest the only reason why I think they’re called dessert boots is because they’re suede. Nevertheless I love the look. Click HERE and HERE and HERE to see a few options.

And for the more price friendly option check out these from Urban Outfitters.

Lastly there’s the hiking boot look. And I’m a fan of this style because it’s the least dressy of the bunch but still gives you some height. It’s the perfect pairing with jeans and an oversized knit. So easy but it will look like you tried.





So there you have it Jen! I hope you find something for you new work look.

Thanks for all the questions and keep them coming!

File photo from Jason Merritt/Todd Williamson/Jeff Vespa/Gettyimages.com