You don’t need to follow trends to be stylish.
I know that sounds backwards when every Instagram and TikTok video is telling you otherwise. Yet after spending over 10 years helping guys master their personal style, I’ve learned that the most confident, well-dressed men aren’t trend-followers. They’re selective about the things they incorporate into their wardrobes.
The pressure to stay “current” can make you feel like you’re always behind or missing something. But constantly chasing trends leaves you with a closet full of pieces that don’t work together and don’t represent who you actually are.
So today, I’m sharing my simple 3-question filter that will help you decide which trends deserve your attention (and your money)—and which ones to skip entirely.
Let’s dive in!
Question #1: Does This Genuinely Feel Like “Me”?
Before you buy into any trend, ask yourself: would I gravitate toward this even if it wasn’t popular right now?
For example, I’ve been noticing lots of giant vibrant prints on men’s button-down shirts everywhere lately. If bold, colorful patterns align with your personality and you’ve always been drawn to statement pieces, then this trend might be perfect for your personal style.
But if you naturally prefer clean, minimal aesthetics and the only reason you’re considering it is because you saw your favorite Instagram star wear it, that’s your cue to pass. That being said, if you want to try it on to test the waters, go for it.
The goal here is distinguishing between genuine attraction and trend pressure. Your personal style should feel authentic to who you are, not like a costume you’re wearing to fit in.
Question #2: Can I See Myself Wearing This in 5-10 Years?
This is where most guys make expensive mistakes. They buy trendy pieces without thinking long-term.
And it’s something I keep reminding my styling clients of: every piece you add to your wardrobe should have staying power. You want to build a collection of clothes you genuinely love, not a museum of fashion moments you got caught up in.
Take the current trend of wide-leg pants. If you think they look cool now, but can’t imagine yourself wearing them in a few years, don’t go swapping out every pant for wide leg. Instead, try one and see how it makes you feel.
Building great style is about making strategic investments that compound over time—that’s where the magic of actually saving money on more expensive clothes comes in!
So instead of constantly replacing your wardrobe every time a new trend flies by, ask yourself if you’d wear it in 5 years (when it’s not trendy anymore).
Question #3: Does This Work with My Existing Wardrobe?
The biggest style mistake busy professionals make is buying isolated trendy pieces that don’t work with the clothes they already own.
Let’s say cargo pants are trending and you decide to try them. Great—new fresh pants, but do you have shoes, shirts, and jackets that work with the baggy aesthetic? Or will you need to buy a completely new wardrobe to make one trend work?
Smart style building means choosing trends that enhance and expand your current wardrobe, not replace it entirely.
If a trend requires you to start from scratch, it’s probably not worth the investment.
Your Next Action Step: Practice the Filter
Want to put this filter into practice right now? I’ve created a guide with 12 current trends from GQ Magazine—each one paired with these exact three questions.
You can literally see trending pieces like “gentlemanly gorp,” “torpedo shoes,” and “bootcut jeans” and practice asking yourself whether they pass your personal style test.
Check out the trend filter guide here
It’s the perfect way to train your eye and build confidence in your style decisions. No more second-guessing yourself or buying something just because it’s popular.
Remember: being stylish isn’t about following every trend—it’s about being intentional with your choices and staying true to your personal aesthetic while remaining current.
You’ll save money, reduce decision fatigue, and end up with a wardrobe that actually reflects who you are.
PS – Speaking of making intentional choices instead of following every trend… that’s exactly what Module 7 of The Style Game Plan is all about.
In this 1 out of 10 modules, I walk you through my complete strategic shopping system, including how to build your personal brand directory, recognize quality construction, and time your purchases for maximum value.
You’ll discover my 50+ curated brand recommendations organized by style and fit, plus the exact quality recognition techniques I use with my private styling clients. No more expensive shopping mistakes or closets full of pieces that don’t work together.
Want a sneak peek at what strategic shopping actually looks like? Check out the image below!
Each module includes a Welcome video, a ~1-hour main video with blog-style text for guys who prefer reading, and an assignment so you know exactly what to do next.
Ready to rock intentional style? Click here to get The Style Game Plan!
