Grandpa Style feat. Ashley Owens

October 6th, 2014

We’ve featured several women wearing tailored menswear as inspiration, such as AmberJenilee, and Karyn. For the most part, though, their jackets and trousers have been sharply fitted and body forming. Ashley Owens, founder of Grandpa Style, on the other hand, wears full-cut menswear. And she wears it very well.

Turns out Ashley and I have a lot in common. We’re both Canadians, basketball players, and tailoring junkies. She’s a trained designer with experience working in world-class tailor shops and she’s a true believer in craftsmanship. ‘Quality over quantity’ is a value that was passed down to her from – you guessed it – her grandfather.

What I love about Ashley’s style is she proves that tailored clothing doesn’t have to be modern or trendy to be stylish. Nor do they have to be slim-cut and body-shaping to be sexy (which applies to men or women). As we’ve discussed in recent Articles of Style articles, there is a certain romance and mystery to the drape of fully-cut cloth that is often lost in today’s overly-skinny silhouettes.

Here Ashley gives us a taste of her personal style near her home/studio in Brooklyn, along with a little background about how she’s making her way in the menswear industry.

1. Grandpa Knows Best

Ashley (9 of 56)

“I grew up all over the lower mainland of British Columbia, Canada. Moving annually for my first 5 years of school, I quickly learned to become an observer… I finally settled down for a longer period of time, living with my grandparents for a few years. I was very close with my grandfather; he’s always been a huge influence on me. He would make furniture in the basement and taught me many things, most notably that good things take time.

My earliest memories all have to do with clothing and style… I’ve always had mixed reactions to my style because I’ve always been very definitive about what I do and don’t like, which doesn’t always resonate with everyone. It definitely meant being teased a lot, but for some reason that never deterred me. Even now I get negative comments but it’s how I like to express myself and how I feel comfortable.

For me individuality is very important, and style can express that immediately.”

Vegasss (1 of 2)

“It’s important to have things properly tailored. Or at least, a fit that is very intentional.”

Slim-fitted or full-cut, what’s really important is the fluidity of the overall proportions. Ashley’s oversized look is consistent and clearly intentional. It’s done with a confidence and expertise that only builds her character.

Ashley (16 of 56)

“The pants were actually my moms, and I had them recut.”

That’s another beauty of tailoring; pieces can be manipulated, updated, and re-purposed in a completely different context.

Ashley (18 of 56)

HVRMINN double-breasted blazer, Shirt by J. Crew, Trousers are mom’s vintage Peter Nygard, Boots are vintage

2. Hone Your Craft

Ashley (24 of 56)

“Before fashion, I was an athlete and played a year of college basketball while studying Political Science. I took a drawing class on the side and came to realize that making art was really fulfilling to me. It showed me that I was missing a creative element in my life. I left school and won a competition that allowed me to go to Milan and shadow Giorgio Armani before one of his shows during Fashion Week. I came back and started working with a painter in Washington State who mentored me and helped me put together a portfolio to apply to Parsons The New School (in NYC). I was accepted into the Fashion Design program and studied for the next four years in their grueling curriculum.

During that time I met some key people that really pushed me to pursue my love for tailoring. One of which is still now my close friend, HVRMINN [aka the soft spoken gangster]. He encouraged me to work with master tailor Rocco Ciccarelli, who I apprenticed with for a summer. In my final year at design school, I worked at his studio to create my thesis which was a line of suits tailored for women… After graduation I interned with the men’s design team at Thom Browne before leaving for a full-time position as Associate Designer with a young locally produced brand, designing tailored goods and outerwear inspired by menswear by cut for women.”

Ashley (29 of 56)

Styling cues we can all use: black hat, black jacket, black jeans, black loafers.

You can’t deny the cool factor of an All Black look.

Ashley (33 of 56)

Ashley (37 of 56)

HVRMINN single breasted blazer, button down, personal custom trouser, Bostonian loafers, stetson hat

3. Breaking Out

Ashley (48 of 56)

“After almost two years working in design I felt the need to work with all the different talented people around me in a collaborative way. I had already purchased the name and had the idea of using it as a platform to talk about ‘slow fashion’, quality over quantity, craftsmanship, etc. More than anything, it was an opportunity to work with others in the industry and share what was important to us.

Now I spend my days meeting with collaborators to put together the next printed issue of GRANDPASTYLE…developing partnerships to make that process easier. I’m also relaunching our website to add a web shop and a more behind the scenes look at our process and our artists…”

Vegasss (2 of 2)

It’s always refreshing to see someone use their personal style to carve their own lane in life. That is what style can do that fashion cannot. Ashley confidently goes against the grain regardless of what others think. She stays true to her aesthetic, her passions, and her point of view.

That’s style. And that can be life changing.

Ashley (54 of 56)

“These pleated trousers are from HVRMINN’s senior thesis at Parsons. They’re pretty special since he handmade them.”

Clothing items are always better with a personal back-story, and in “slow fashion” there’s often room for several.

Ashley (55 of 56)

Denim jacket by Pepe, Vintage waistcoat, Shirt by J. Crew, Trousers by HVRMINN, Loafers by Bostonian



Thanks for reading and special thanks to Ashley for participating!

Yours in style,

Dan Trepanier


Photography by Alex Crawford

  • Frmnytotx

    She’s pretty fly

  • tuba

    Beside having great style, she is beautiful- thought I’d put it out there guys.

  • JoeFromTexas

    That last look is the best – those pants are perfect, or maybe it’s the blacked out look. But who would have expected a flowing DB to look so great on a woman, maybe that’s the best look.

    Y’all have had a few features that gave tips for different body types, and I think this post could fit into that, since Ashley is an athlete. What I really like is how the proportions and drape really flatter her athletic build without hiding her femininity. From this post and her site linked, it’s clear Ashley is quite a talent.

  • Levitate Style

    The all black everything look is on point!

  • Vic

    This much like your other women in menswear posts are one of your all time greats! Keep up the good work guys because you truly inspire.

  • K

    SUCH A GREAT POST. Inspiring style and attitude.

  • ghg

    the day i found a girl like that i would end my bachelor life

  • Ali Naaseh

    First look is dopey, second look is money, third look is solid

  • Steven Santander

    Ashley is amazing, I’ve had my eye on her work for a while and she is one of my favorite people in menswear. Her eye for proportions and minimalism is incredible. Beautiful woman with beautiful looks as always. Thanks for this one TSB!

  • ChrisD

    Love the 2nd (all black) look, even the untucked shirt. Grandfathers are special people. I will definitely be watching her site.
    Great content lately.

  • TO

    Amazing story, amazing lady. Her story makes her sound like the Steve Nash of fashion! :)
    Look 3 is an absolute masterpiece. Treading perfectually equal between feminine and masculine– I was just enamoured with the trousers (and their perfect slow top-to-bottom taper) at first look, and from reading their origin I can see why they are special.

    • buster curley

      Ya, great story. It gives me pride and hope when I read about middle class white people making it in the fashion biz.

  • Juan Zara

    It’s really inspiring to see this kind of determination and passion about clothes. Like Ashley, I’ve also inherited my passion for menswear from my grandfathers (both of them), and I can really feel her style draws a lot from that source of inspiration.
    Great photographer (check out HVRMINN’s profile on her website!) and such a beauty!
    Great piece, thanks TSB!

    • TO

      Nice Juan — I also was originally inspired to menswear by my “Bampa” [grandpa]… Have any photos to share?

  • Nate

    She’s a goddess in every way. Intelligent, creative, confident, stylish and beautiful. Great post gents.

  • Vincent Nappi

    Absolutely love what she does over at Grandpastyle. Her aesthetic and photography are ridiculously inspiring. Great that you guys put together a feature with her!

  • Amelia

    This is such a great post, it really goes to show that women can get into the world of menswear. All of these are great, but look three is especially on point: vest and denim jacket is such a killer combo. Thank you so much for featuring a girl!!

  • AdamE

    Great post, although in the description for the first look, I believe you’re referring to the manufacturer for the shirt, not the shit…

    • JoeFromTexas

      I don’t know – JCrew makes some dope shit…

      • AdamE

        They make some dope shirts too…