Ask Sissy: Our New Fashion Editor-at-Large

Looking for a way to break the rules with a few new ones to live by, we teamed up with Sissy Sainte-Marie last year for a series that broke us free of skin-tight jeans and body con, and made us appreciate coat season a whole lot more. If you’ve been following along, you’ve probably already met Sissy and taken a few notes. So we are beyond excited to announce this rad lady is now our Fashion Editor-at-Large. She will be penning a column every month and sharing her sage style advice, and signature deadpan. Man, we love her.

To kick things off, we compiled a few of your frequently asked questions and outfit woes for her to answer.

Q. I’VE READ A LOT THIS PAST YEAR ABOUT THE CAPSULE WARDROBE. WHAT CLOSET STAPLES SHOULD I REALLY BE INVESTING IN? – Christine, Washington, DC

A. I am a person who dreams night and day of the ease of a daily uniform and a capsule wardrobe. But, I love clothing and tend to lack impulse control in acquiring more and more of it. In my line of work I get offered a lot of gifts, store credits and trade. Sometimes I end up impulsively choosing things I never end up wearing more than once. Or I pounce feverishly on one item that goes with nothing I own and end up buying four more things to build an outfit around that thing I didn’t need in the first place. An overflowing closet paired with a depleted bank account is never a good look.

I know I’m not the only one going through this cycle of absurdity. I think the renewed focus on a capsule wardrobe is a reaction to the relentless flow of trends we are bombarded with ad nauseam. It can get to a point where we feel suffocated by our stuff and begin to radically reject the constant pressures of consumerism in order to protect our mental health, our savings and our planet. It is only natural to see an interest in buying less, choosing versatility and practicality over ephemera.

When you find that perfect black turtleneck sweater. Isla Sweater by Shaina Mote
When you find that perfect black turtleneck sweater. Isla Sweater by Shaina Mote

 

The particular items for your capsule wardrobe should be determined by your individual lifestyle, tastes, and day-to-day needs, but I can give you some guidelines for investing. I have actually been devising a point system for smarter shopping because I’m a geek like that.

The questions:
– IS IT A STAPLE? CAN IT BE WORN ON A REGULAR BASIS / EVERYDAY?
– IS IT APPROPRIATE FOR A VARIETY OF OCCASIONS AND SETTINGS?
– DO YOU NEED IT RIGHT NOW?
– IS IT VERSATILE / ABLE TO BE WORN WITH AT LEAST THREE THINGS YOU CURRENTLY OWN?
– IS IT WEATHER APPROPRIATE RIGHT NOW?

Scoring: 1 point for each yes answer. Prioritize purchases accordingly.

TIER 1: 4-5 points (Example: a black turtleneck, canvas sailor pants, black ankle boots, a trench coat)

TIER 2: 3-4 points (Example: a warm coat, a white cotton shirt or blouse, vintage jeans)

TIER 3: 1-2 points (Example: low heel pump, suede sandals, a black dress)

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White shirt, black pants, never goes wrong. Lemaire Two-Pleat Pants.

 

Fine tuning:

Buy now or later? Determine what to buy now and what to save for later. I know I will need some new sandals soon, but today I’ll buy black ankle boots to replace the ones I wore to oblivion over the last two years.

Buy this one or that one? Determine what’s the most practical and durable. I had my eye on four white prairie-style blouses. I opted for the one with the least embellished neckline and I chose cotton over silk. Avoid items that require dry cleaning and feel fussy on your body or too fancy to wear in your daily life.

Is it too similar to something I already have?
Unless it’s a second black turtleneck that you need for rotation due to frequency of wear, avoid buying redundant items. Instead, purchase something that fills a gap in your wardrobe rather than say, a fourth leather bucket bag. Maybe a camel sweater, but not a forest green one, or Kamm pants in a new neutral color, if that’s what will round out your capsule wardrobe.

Is it a safeguard? Sometimes we must make precautionary purchases that will provide peace of mind when the inevitable day comes. Rain boots, sure, but more importantly heels. You’ll no doubt need a pair of heels for more formal events and occasions. Invest in a simple closed-toe pump in black. Whether or not you end up wearing them as often as loafers or boots, they will be essential in a pinch and you’ll be glad you have them handy when you get that last minute invitation. Same goes for a party-ready black dress or jumpsuit.

Is this right for my lifestyle? Can you wear beautiful flowing wide leg trousers on the daily or is a fine cotton twill more your bag? What’s the dress code at your place of employment? Do you attend a lot of meetings and events for which you need to look spiffy? Or do you need to get down and dirty at work? Be careful to not buy clothing that doesn’t suit your needs. It will end up unworn and wasting space. Buy what you’ll get the most use out of.

But…but… Do I just like it and want it despite it being completely impractical and something I’ll only wear fewer times than I can count on one hand? Sometimes a “yes” answer to this question trumps the point system, moving an item to the top of the cart. You gotta have a little fun! But these purchases are only advisable once you have your capsule wardrobe firmly in place. Without starting the cycle of suffocating consumption all over again, strive for 90% practical and 10% trophy items–or whatever ratio brings you the most peace of mind. So, if you really want that tassel choker, honey, you go and get it!

Try it now. Go fill up your Garmentory cart with anything that strikes your fancy and follow the steps outlined above. I can’t wait to see what you choose!

Shop Sissy’s Picks >

 

Q. HOW DO YOU KNOW WHEN A TREND IS RIGHT FOR YOU? IT’S FUN TO TRY SOMETHING NEW BUT HOW DO YOU KNOW IF IT WORKS OR IF IT REALLY DOESN’T? – Laura, Toronto, ON

A. Well, I think it simply comes down to how you feel in it. I never thought I’d be a jeans person until I tried on the right pair. I wish I could be a sneaker person, but I’m just not feeling it, or any sportswear for that matter. But I sure love seeing it on other people who wear it well. Somewhere between being in a style rut and being a try-hard, there’s a world where comfort meets courage at the heavenly axis of our own truth. I do advise looking to runways, street style photos, print magazines and Instagram influencers for inspiration and fresh ideas. You may want to try a small fraction of them. But when you’re in front of the mirror, search for an honest feeling inside. You should always feel at ease, and unapologetically fabulous in what you’re wearing. Weather you are walking on Bic lighter heels or cushy Air Max soles, you should feel like you are walking your in your own lane. Always keep in mind this quote from Iris Apfel: “The worst fashion faux pas is to look in the mirror and not see yourself.”

Have you given off-the-shoulder tops a go? Signature Annie Top by Sincerely, Tommy.
Have you given off-the-shoulder tops a go? Signature Annie Top by Sincerely, Tommy.

 

Knowing who you are style-wise may take years to master through trial and error. That is why I advise trying things on just for the hell of it. How else are you supposed to know? Avoid trips to anxiety-inducing, big brick and mortar stores with their overly crammed racks, tiny dressing rooms, bad lighting, and pushy salespeople. Impulse buys under these circumstances will be a set-back on your journey. Take advantage of the sweet return policies of online retailers and order up a storm of trends so you can try whatever you want in the privacy of your own home at your leisure. Do this alone. Don’t go taking polls from your friends, family, roommates or social media followers. It needs to look and feel right to you and you alone.

What you find may surprise you. A beige linen suit that you imagined would be so conservative and mumsy on you, might feel radically fresh and unexpectedly rebellious in it’s smart simplicity once you give it a whirl. A modest, oversized dress may make you feel more dignified than dowdy. You may feel more tough and empowered in a waist cinching sundress than a borrowed-from-the-boys ensemble. That Issey Miyake that looks all crazy on the hanger might touch you in all the right ways and be your magic portal into a new style dimension. Or, you might try a bra top over a button down shirt and say, “I look like a frumpy dumb dumb.” Ah-ha moments abound with an adventurous spirit and free returns.

Shop Sissy’s Picks >

 

Q. I LOVE LOOKING AT ALL THE BRIGHT HUES DURING FASHION WEEK, BUT I HAVE A PRETTY SEVER PHOBIA OF COLOR IN MY OWN WARDROBE. HOW CAN I TRY IT AND FIND WHICH COLORS WORK FOR ME? – Shannon, Minneapolis, MN

A. Funny you should ask because I was on a similar journey in 2016. My go-to palette mostly runs the gamut from cream to beige, but like you I’ve been thinking a lot about trying to get outside the box, even dedicating a Pinterest board to colors and combos.

When I was a kid, all the moms and grandmas went to these Color Me Beautiful parties to determine their “season” which would act as a guide to which colors looked best on them. (Peach and turquoise if you were lucky in 1985.) Since you’ve already admitted to being color-phobic, taking Carole Jackson’s season analysis quiz may only serve to induce a panic attack if periwinkle and magenta show up on your swatch of advisable colors.

To start, ease into color by opting for garments and accessories in muted tones like sage green, mustard, plum, garnet and amber. These tones can act as new neutrals, pairing well with black, brown, beige and ecru currently in your closet. Evolve into brighter colors starting with accessories such as lime green sandals or an egg-yolk-yellow bag. These colors will also pair well with more traditional colors like charcoal, navy or olive, likely already in your wardrobe.

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Pairing a bold skirt with neutrals softens the blow. Maryam Nassir Zadeh Renata Pleated Skirt in Acid.

 

Once you’re ready to take a further plunge into bright colors, don’t start mixing it up right away. First opt for a dress or jumpsuit in a bright color that looks good on you. Remember all the chic ladies who were photographed wearing the tangerine-colored Rejina Pyo dress during fashion week? You can do it, too. Get yourself a brightly colored dress or jumpsuit to wear to an event or occasion this spring. Feel good? Feel powerful? If so, start wearing dresses and jumpsuits in similar colors for everyday. Then try pairing it with with statement footwear.

After you feel a sense of mastery with dress/shoe combinations, you’re ready to move onto separates. Try pumpkin-orange pants with a sky blue top and fire engine red shoes. (But please don’t wear khaki pants with a red top unless you work at Target.) If you’ve found your calling, you’ll soon be playing sartorial-jazz like you’re on Alessandro Michele’s Gucci catwalk, piling on prints, textiles and accessories of every hue. If, on the other hand, you felt like a Teletubby in that chartreuse pant suit you wore to your cousin’s wedding, let yourself off the hook and run back to those ride-or-die neutrals. Bright colors aren’t for everyone and that’s okay. We can’t all be as fly as Miss Frizzle. True style is about knowing what works best for you. But, at least you can say you tried.

Shop Sissy’s Picks >

Have a burning style question you want answered? Comment below! Our Ask Sissy column will be back in the Spring.