How to Be Bold in Your Life

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

By Taylor Davies | Last Updated: Aug 7 2019

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? Maybe not.

Quitting your job without another one lined up? That’s a bold move. Proposing to a women with a ring you picked out without even peeking at her Pinterest for inspiration? 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. So I’m sharing a few tips on how you can infuse your life with a little audaciousness.

AKA, how to be bold in big ways and small.

So! Check out 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:

Ready to get bold? Well then, read on…



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 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, instead, 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 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.

A bold look for a bold move:

Double-monk strap shoes

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 a monkstrap shoe and prepare to make your main squeeze swoon. The double monkstrap style is an SG-certified bold look that will take you far—a style in a rich brown or 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.

As much as I love them, I’ve recently decided to cut back on earning miles for celebrating other people’s milestones 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.

A bold look for a bold move:

Wear-everywhere athleisure shorts

There’s just something about the evolution of guys’ casual shorts that we’re very into at SG HQ. It probably has something to do with each and every one of us having major crushes on boys who rocked basketball shorts pretty much every day through middle school.

Today’s version of “wear everywhere” athletic shorts are in copious supply with athleisure brands like Rhone, Olivers Apparel, and Outdoor Voices. Wear yours with everything from your favorite pocket tee to your most-loved OCBD.


Career Gear (via GQ)


To say that national tensions have been running high recently would be the biggest of understatements. 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, 30-something 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!)

A bold look for a bold move:

via Bonobos

A still-stylish suit you’re ready to part with

I bet you could think of a suit in the back of your closet right now that you barely wear, one that would make an excellent donation for Career Gear. Maybe you’ve outgrown it, or maybe you just never get to wear it at your dress code-free job.

Whatever the reason, lighten up your closet’s load and do some good at the same time. Everybody wins!


Ready to make big moves in your wardrobe? Tell a member of Team SG what you need, and she’ll put together a personalized shopping plan, built just for you, your personal style preferences, budget, and body type.