Menswear Muses feat. Karyn Bailey

March 11th, 2014

Maybe it’s just me, but I find that well-tailored menswear looks just as sexy (if not sexier) on women than it does on men.

The best part is, women have more freedom (and therefore more fun) with fashion styling, making them the perfect muses of classic menswear. Naturally, they take more risks with colors, fabrics, proportions, pattern-mixing, accessories, etc. so their combinations can be very inspiring.

For example, two of my female style icons Esther Quek and Sarah Anne Murray (both international editors of The Rake magazine) are known for their womanly take on sharply tailored menswear. In fact, this colorful separates look was the inspiration behind my “turtleneck undershirts” post. 

I wanted to have some fun with this concept, and play a little dress-up with my beautiful friend Karyn. She’s not typically such a dapper menswear dresser, even though she’s secretly been helping me develop the Articles of Style brand for years. So here I styled Karyn in three classic menswear ensembles – to encourage our female readers to try some classic menswear and remind our male readers to look toward the more fashion-inclined sex for inspiration.

1. Bolo Tie Revolution


Bolo ties are just beginning to trend in menswear (although Alex and I both saw them regularly growing up in the country). It’s a great alternative to a classic necktie, and an easy way to take a grey suit + white shirt combo in a non-corporate direction.

I found this polished rock & leather bolo at a local LA flea market, but eBay is also a great place to score them. If you’re apprehensive about trying a bolo start by trying it loose around the neck, more like a necklace than a tie.


Suit by Hugo Boss, Shirt by Brand, Bolo tie Vintage, Hat by Stetson, Shoes by Saks Fifth Avenue. All clothing available at Saks Fifth Avenue (Beverly Hills and select locations.

2. Old Money Prep


The classics always look good, like a navy blazer, pale french cuff shirt, knit tie, and grey glenplaid trousers.

The tailoring is menswear-inspired, but the accessories (watch, cufflinks, tie bar, umbrella) are vintage men’s pieces from my closet.


Navy blazer by Akris Punto, Pink french cuff shirt by Hugo Boss, Wool glenplaid trousers by Theory, Kilted oxfords by JCrew, Gold jewelry Vintage (Dan’s). All clothing available at Saks Fifth Avenue (Beverly Hills and select locations).  

3. Country Weekend


Another universal combo that will never get old: brown felt hat, tweed blazer, preppy striped shirt/tie combo, dark denim, suede boots.


Hat by Stetson, Tweed riding jacket by Ralph Lauren, Shirt by Saks Fifth Avenue, Tie Vintage (Dan’s) Jeans by Levis, Suede boots by Dolce Vita. All clothing available at Saks Fifth Avenue (Beverly Hills and select locations).

Thanks for reading, and special thanks to Karyn for participating (and putting up with my sh-t). I am a very lucky man to have such a beautiful, worldly, and supportive best friend and bride-to-be.

Yours in style,

Articles of Style

Photography by Alex Crawford.