Style Sense: Condessa Croninger Wears Many Hats

. July 12, 2017.
Summer 2011: Very dramatic, but also very “costumey.” It’s what I wore to Zoo-to-Do that year. (1999 Jacobson’s Teen Shop dress, self-painted snow leopard adornment).
Summer 2011: Very dramatic, but also very “costumey.” It’s what I wore to Zoo-to-Do that year. (1999 Jacobson’s Teen Shop dress, self-painted snow leopard adornment).

Name: Condessa Croninger
Age: 48
Occupation: Art Director, 20 North Gallery

You’re so elegant— have you always been this way?

Since childhood, I have been fascinated with the possibilities inherent in defining identity through clothing. I loved playing “dress up,” and I have always loved clothes. I am fortunate to come from a family of very stylish women— my grandmothers, especially, were extremely well turned out, each in her own way.

Tell me about your hats. When did you start wearing them?

I first started wearing a hat (a Bombay Bowler pith helmet) as a fashion accessory at age 17, when the film Out of Africa debuted. Meryl Streep! Robert Redford! Sweeping vistas! Timeless romance! All this was mine when I wore my hat. I’ve been hooked on hats as a “fashion necessity” ever since.

(LEFT) Fall 2008: Great outfit—but not at all seasonal and taken at a gallery that closed in 2011. Showing my favourite bespoke skirt and my ladylike high heels, black kid gloves, black patent leather MaxMara bag (Jacobson’s 2002), 2004 fitted jacket from Ann Taylor, Wolford turtleneck, hat (by bMichael, under the joebillmiller label, from Jacobson’s, 1998), vintage mink boa (estate of Joe Ann Cousino). (RIGHT) Summer 2011: Very dramatic, but also very “costumey.” It’s what I wore to Zoo-to-Do that year. (1999 Jacobson’s Teen Shop dress, self-painted snow leopard adornment).

(LEFT) Fall 2008: Great outfit—but not at all seasonal and taken at a gallery that closed in 2011. Showing my favourite bespoke skirt and my ladylike high heels, black kid gloves, black patent leather MaxMara bag (Jacobson’s 2002), 2004 fitted jacket from Ann Taylor, Wolford turtleneck, hat (by bMichael, under the joebillmiller label, from Jacobson’s, 1998), vintage mink boa (estate of Joe Ann Cousino). (RIGHT) Summer 2011: Very dramatic, but also very “costumey.” It’s what I wore to Zoo-to-Do that year. (1999 Jacobson’s Teen Shop dress, self-painted snow leopard adornment).

How do you decide what your hairstyle will be?

You may not believe it, but as far as grooming is concerned, I am actually a very low-maintenance individual and very much a creature of habit. I have had the same haircut since 4th grade: one length, pulled back, out of the way. Now I wear it up in the exact same ballet bun, every-single-day (although I do change chignon styles about every 10 years). Wearing the hair up makes it fit nicely under hats.

What’s more important: your hair or outfit? What decision is made first?

Always the outfit! If it’s vintage and the occasion warrants a specific look, I will sometimes modify my updo to reflect a certain decade.

Do you focus on any specific designers or time periods when collecting vintage?

I haven’t really collected vintage so much as inherited it. The occasional estate-sale hat or pair of kid gloves notwithstanding, almost all my vintage outfits and accessories have been either gifts from friends who are happy to know that their ancestors’ beloved ensembles will continue to be loved (and worn) by me, or they come literally from my favorite vintage outlet: “grandma’s closet.” Both of my grandmothers ended up with closets filled with exceptionally lovely clothes. And both were my size!

Style icon?

Other than my gorgeous and stylish grandmothers, mother and aunts? If I had to name someone outside the family, she would be Diana, Princess of Wales. Not so much for her clothing choices (far more colorful and contemporary than mine), but because her look was always uniquely her own. Once she established her personal style, it was her gauge for every outfit, adapted to the occasion. Her clothes were never really in style, they were her style. The fashion world copied her, rather than the other way ‘round— truly iconic!

Early spring 2013: Summer attire. Purse, shoes, hat (by bMichael, under the joebillmiller label, from Jacobson’s, 1994) are mine, but jewelry and “luncheon suit” are what I was modeling for a friend’s used/vintage clothing shop. However, the suit is the exact same one I almost bought (Terri Jon for Rickie Freeman label, from Sophia Lustig in 1999) for the Kentucky Derby. So I guess you could conceivably call it one of my (very nearly) style choices…

Early spring 2013: Summer attire. Purse, shoes, hat (by bMichael, under the joebillmiller label, from Jacobson’s, 1994) are mine, but jewelry and “luncheon suit” are what I was modeling for a friend’s used/vintage clothing shop. However, the suit is the exact same one I almost bought (Terri Jon for Rickie Freeman label, from Sophia Lustig in 1999) for the Kentucky Derby. So I guess you could conceivably call it one of my (very nearly) style choices…

What type of garment or accessory do you have the most of?

Unquestionably, the hats—my collection currently numbers 344, ranging from the 1880s to this season. Bonnets to boaters to Bretons to (my Mud Hens) ball cap! The “accessory” I have least of is space enough to store them all. It’s probably time to start deaccessioning…

What do you feel best when wearing? Describe that feeling.

My favorite outfits are amalgamations of vintage and contemporary pieces, replete with accessories that “finish” the total ensemble. I prefer well-fitted, tailored skirts and jackets because they stand out and make a distinctive statement today, causing me to feel confident and assured. And if part of the day’s outfit is something that was my grandmother’s, it feels like wearing a warm hug. That’s even better.

Less or more?

Just right— one knows when it’s achieved.

How long does it take for you to get ready on a typical morning?

Surprisingly not that long, although it depends on the occasion. I always lay out at night my outfit for the following day (since I never make my best decisions in the morning!) and the rest of “daily me” is easy to throw together. For meetings and the gallery, I can go from coffee to key-in-the-ignition in 45 minutes or less. Ironically, it is casual occasions that stymie me the most—those outfits can take hours to put together. I have a horror of looking like I am trying to pull off a very unconvincing disguise of “casual me.”

(LEFT) Winter 2015: Dressed for “winter sport,” in vintage 1980s fox fur hat, my grandmother’s skates and sweater that she knitted herself, combined with puffy vest and jeggings. (RIGHT) Early spring 2015: Work attire—contemporary bag and (favourite) shoes & gloves, my hat by bMichael (Jacobson’s 1998), fitted jacket (from Ann Taylor, 2004), my grandmother’s skirt (made by herself, ca. 1950) in our family tartan: Maclaine of Lochbuie, with matching man’s tie (I purchased in Scotland in 1998).

(LEFT) Winter 2015: Dressed for “winter sport,” in vintage 1980s fox fur hat, my grandmother’s skates and sweater that she knitted herself, combined with puffy vest and jeggings. (RIGHT) Early spring 2015: Work attire—contemporary bag and (favourite) shoes & gloves, my hat by bMichael (Jacobson’s 1998), fitted jacket (from Ann Taylor, 2004), my grandmother’s skirt (made by herself, ca. 1950) in our family tartan: Maclaine of Lochbuie, with matching man’s tie (I purchased in Scotland in 1998).

You’re stranded on a desert island and can only bring five things from your closet — what do you grab?

What’s the weather like on this island? If it’s 70◦F and partly sunny (not to mention well-paved and dry), I’d pick my bespoke 19” black pencil skirt in 4-season wool crepe; my opaque black tights (always 2 pairs, actually, for warmth and extra opacity); my ladylike black suede high-heeled, pointed-toe pumps (matched with the tights, they visually lengthen and define the legs); my Wolford seamless fitted black turtleneck (from the Sophia Lustig Shop!); and a pair of wrist-length, single-button, black kid gloves. Presumably, I will be able to fashion a smart broad-brimmed hat, shell purse and jewelry from island botanicals to add colour and complete my ensemble. Rats! I don’t have any way to provide myself a tailored jacket; maybe I can get it shipped from home?

How big of a bag do you pack when you go away for the weekend?

You say “bag” as if it is only a singular item?

Best sartorial rule to break?

The fashion industry would have one believe that comfort, informality and appropriateness are all synonymous—this correlation is largely apocryphal. Therefore, throw “fashion” to the winds! Dress appropriately to be truly comfortable.

Best sartorial rule to follow?

If in doubt, it’s better to overdress a little. By doing so, one pays a compliment to others by demonstrating respect for the importance of the occasion. (And it’s always easier to tone it down, rather than try to dress it up, once everyone else arrives.)

Most memorable style advice?

Style is all about demonstrating persona through clothing choices. Every outfit, every day is a small piece of performance art that becomes the hallmark of the wearer’s identity. So— dress yourself!

Best compliment you could ever receive (or have received):

Oh, you look so much like your grand/mother!” (Beautiful ladies, all).