Lessons from the Best-Dressed List

Lessons from the Best-Dressed List

What you can learn from the heavy hitters
lessons from the best-dressed list jeff goldblum vanity fair

By Megan Collins | Last Updated: Jan 27 2019 | 3 min read

As we start to research the seeding for SG Madness 2019, we’ve been digging through plenty of best-dressed lists from the past year. From Vanity Fair to GQ, there’s plenty of variety when it comes to recent style leaders. Think: heavy hitters from entertainment, business, fashion, and even royalty. And whether it’s Hollywood newcomers like Lakeith Stanfield, or music phenoms like Mark Ronson, there is a lot of latitude for what constitutes great style. So we thought we’d share a few lessons from the best-dressed lists. Why not share the wealth?

These men offered up wisdom for the well-heeled man, whether those heels come attached to wingtips, sneakers, or a boot with just a little extra heel even (we see you, Harry Styles).

Below, five lessons from the best-dressed list:

lessons from the best dressed list


The men on these lists were quick to name their favorites—from watches to sneakers to tailors. The lesson? Finding what works for you and sticking to it isn’t boring, it’s smart! Life becomes abundantly easier when you have fashion fall-backs. Pieces you know work for you, every time. Personally, for me, it’s a dress and tights combo that, when all else fails getting dressed in the morning, I can throw on and walk out the door feeling confident. Wisely, I keep plenty of tights stockpiled, further lowering the likelihood of fashion paralysis.

Though tights are (probably?) not your thing, it’s worth considering what is. Because the more pieces you have like this in your closet, the better.


Designer Alber Elbaz, a roly-poly little thing of a man, is instantly recognizable in the fashion industry for his standard uniform of velvet blazer and floppy bow ties. Ryan Gosling has his trucker jackets. Elbaz and Gosling embraces their respective fashion wheelhouses.

Ask a friend, “How would you describe my style?” and if the answer comes easily (preppy/sporty/urban/etc) you’ve mastered a look that’s distinctly “you.” Of course, you can always incorporate new trends and pieces into your wardrobe by pairing them with your favorite standbys. That way, you’ll never feel like a fish out of fashionable waters.

> Need help figuring out your style? Read this


When asked to name a “style idol,” several names came up again and again, like Steve McQueen, Paul Newman, and Cary Grant. Don’t be afraid to play copy-cat; the greats have always relied on the wisdom of mentors. From Kobe and MJ to Mark Zuckerberg and Warren Buffet, it can be helpful to look behind you to clarify what you want your fuure to look like.

Feel free to crib fashion notes from your own style mentor. After all, imitation is the sincerest form of flattery. And yes, those mentors can be fictional. If you want to name check suave spy James Bond as the man whose look you want to emulate, imagine how helpful that will make your shopping trips. Hmm, would 007 wear these pleat-front khakis? No? Put ‘em back on the rack.


Over and over, the terms “well-loved,” “broken-in” and “classic” came up when these men discussed their style. What goes around, comes around. Nowhere is this more true than fashion. Whether that’s your dad’s retro elbow patch corduroy blazers to a pair of classic Aviators—if it looked cool growing up, it could again in 2019.

The lesson behind the lesson? Buy quality pieces and your wardrobe will work harder for you! Well-made items—like good leather boots and a durable topcoat—will age with you.


Rapper and producer Pharrell Williams’ list of favorite clothes includes several designer pieces…and his Spongebob Squarepants socks.

Put simply: if you like it, wear it.



I started Style Girlfriend to help guys look, feel, and act their best.