The Guy’s Guide to ‘The Bold Move’

3 easy ways to step your game up—for good.

I have always loved the expression, “That’s a bold move.” I throw it around a lot with my friends, but sometimes I think it’s a bit of hyperbole. Is eating cured meat the day after the sell-by date really a bold move? Is taking the E train to JFK airport instead of an Uber really a bold move?

Quitting your job without another one lined up? That’s a bold move. Proposing to a women when you’re not entirely sure she’ll say yes? Say it with me: Bold. Move.

It shouldn’t surprise you to hear that the entire SG team and I are all about daring behavior in all aspects of life, from work to relationships, and of course, style. To that end, Style Girlfriend has partnered with Ace Marks—a shoemaker you’re about to be obsessed with—to share a few tips on how you can infuse your life with a little audaciousness (yes, that’s a fancy synonym I found on the internet).

Ace Marks has built their brand around distinction and a taste for the unique; they’re known for statement-making shoes (think unexpected contrastic colors and fabrics) you won’t find anywhere else. Working with artisans in Italy, they handcraft their luxury brogues, boots, monk straps and loafers in small batches, making each style and colorway a uniquely limited run.

Ace Marks also runs a one-of-a-kind buyback program that donates customers’ old pairs of Ace Marks shoes to men in need through Career Gear (also SG’s social impact partner)! Just send in your old pair, and you’ll receive a $50 credit towards purchasing a fresh style. Right now actually, they’re so confident that guys like you will love their shoes that they’re buying back any brand of dress shoes in exchange for a $50 credit to their site, so you can try a pair for yourself at a discount while also helping out a fantastic cause.

Ahead, we’ve outlined three ways you can be a little more courageous in your everyday life—ways that might even inspire a pal to shake your hand and say, “Now that was a bold move.”

Below, three tips on how to be bold:


At first, my suggestion for the bold move here was going to be something like “Call her on the phone!” or “Ask for her number in person!” But I read the Style Girlfriend comments, and I know that many of you astute, intelligent gentlemen out there happen to think it’s crazy not to call a woman on the phone. So I’m skipping ahead a few levels and going straight for cinematic-level fearlessness. I’m talking about making a Grand Romantic Gesture—heretofore referred to as the GRG.

Remember that moment when Seth asked Summer to stand on top of the kissing booth and declare her love in season one of The O.C.? Or how about this extremely cheesy proposal video that makes me cry every time I watch it (which I swear is not that often)? Those are amazing GRG moments that I think we could use more of in our actual, not-made-for-YouTube-streaming lives.

Here’s the thing: If you usually text the women you date, a GRG can be a phone call just to talk and catch up. If you usually order in takeout on date night, cooking something and picking up a bottle of wine totally counts as a GRG. Showing up with flowers just because? You guessed it— GRG, big time.

What makes a romantic gesture “grand” is the way it feels set apart from your routine, and from the way things usually are. It doesn’t have to be lavish, expensive or coordinated with sixty of your closest friends; it just has to be sincere, and sincerely unexpected.


I once had a very serious internet crush on a man who lived for a good pair of double monk strap shoe. I found the look so appealing, mostly because it was unlike anything the IRL men in my life ever wore. The GRG is an occasion worth dressing sharp for. Tuck a micro-floral shirt in a dark color into a pair of slim chinos, buckle into the Ace Mark Monkstrap and prepare to make your main squeeze swoon. The double monkstrap style is an SG-certified bold look that will take you far—the rich ‘Brandy’ color will go perfectly with your best navy suits and formal looks too; think weddings, work events, etc.


I don’t know about you guys, but about 90 percent of my travel plans since age 28 have involved shuttling myself by planes, trains and automobiles to get to someone else’s wedding or pre-wedding event. Ceremonies in Seattle. Bachelorettes in Sonoma, engagements on the Upper East Side—you name it.

I’ve recently decided to cut back on earning miles for celebrating other people’s milestones (as much as I love them) and to start hitting some of my own. I haven’t really traveled alone since I studied abroad in college, unless you count that time I went to a Sandals resort by myself. I’m desperately in need of an adventure—and I bet you are too.

Maybe it’s something as low key as driving to Portland to visit your grandparents and taking an extra day to explore on your own. Maybe it’s a full Eat, Pray, Love sabbatical overseas. Perhaps you just need to rent a tiny Airbnb upstate to unwind with a book and a bubble bath for a day or two.

Traveling on you own is a bold move because it will challenge you to get outside yourself. You’ll either plan your trip down to the minute or you won’t—and the only person it will affect is you! You could make new friends, check something major off your bucket list (Niagara Falls, anyone?), or find out that you absolutely cannot behave normally while eating alone at a restaurant.


The savvy, intrepid traveler has no room in his carry-on for superfluous footwear. Along with your favorite slim-cut jeans, layering pieces on top, and one great piece of outerwear (like a peacoat), pack a versatile pair of boots. Ace Marks’ Troy Chelsea Boots are equal parts business and pleasure thanks to their contrasting brown leather and suede design—perfect for days spent exploring the cobblestone streets of Dublin and nights chatting up Irish girls in Temple Bar. (I’m just spitballing here.) Packed alongside your passport—or at least your E-Z Pass—you’ll be ready for anything.


To say that national tensions have been running high since the election would be the biggest understatement of 2016. Every day, I’ve logged onto the ol’ internet machine to a near-constant stream of encouragements to get out there and “Do something” on my social media channels. (If that’s a bubble, it’s one I’m totally okay with.)

I’ve been thinking about what I—Taylor Davies, 31-year-old female living and working in New York City—can actually do. For the past six years I’ve volunteered my time with a non-profit that aids orphans in Malawi. More recently, I’ve been trying to convince my roommate that we should foster a pet that’s up for adoption at one of our local animal shelters.

Whatever your time availability might be, whatever causes stir something inside you—try getting out there and doing something about it. Anyone with the means can give money (and we think that’s great!), but in the age of Netflix binge-watching, it’s extra-bold to give up your free time to someone or something else—especially this time of year. It makes a difference and it can change a life, including yours. (Exit stage left from my sappy speech!)

THE LOOK: Remember that awesome program I mentioned at the beginning of this post? Ace Marks ‘Leave Your Marks’ program is the perfect example of going above and beyond in an unexpected way. I bet you could think of a pair of shoes in the back of your closet right now that you barely wear, ones that would make an excellent donation for Career Gear, and give you some extra incentive to spiff up your everyday wardrobe with a fresh pair. The Ace Marks’ Cap Toe Griffin has a cushioned leather insole, extra-flexible construction and is lined from heel to toe in calf-skin for some serious softness—lace those bad boys up and pair them with your favorite sport coat and chinos for a sophisticated office-ready look with a bit of an unexpected twist.



Presented by Ace Marks. Thanks for supporting the great brands that make Style Girlfriend possible.