31 Days

Day 24

Break Out
of Your Style Rut

Man outfit dressing illustration

When it comes to getting dressed, you know what you like. You know what you feel good in. But that's what makes it easy to fall into a routine of the same 'ol, same 'ol when it comes to your wardrobe. And that's not always a bad thing. Developing a personal uniform can save you from making a lot of choices in the morning and ensures that you always look and feel your best.

But if you're getting asked “Didn't you wear that yesterday?” or if you've noticed that you look the same in every photo people post of you, it might be time to switch things up. Maybe you look at the clothes currently hanging in your closet and feel a little uninspired. Now is a great time to shake things up and experiment.

Man outfit dressing illustration

We're not talking about a complete overhaul, just injecting some freshness into your everyday outfits. What we wear plays a big part in the way we think about ourselves, so these suggestions will help you shift to a new vibe without looking like you completely abandoned your signature style.


Start With
a Declutter

A smart starting point is to get rid of the items you don't wear. You probably know the ones—there might even be a little dust on the top of those hangers. Items you got on sale and thought you'd wear, but never quite felt right. Things that no longer fit and older items that were replaced by more beloved clothing. If you haven't worn it in the last year, you're probably not going to wear it in the future. Getting rid of them not only gives you a clearer view of what you have, but it helps you identify gaps that need to be filled.

Todd Snyder Dylan Italian Suede Snap Jacket

Dylan Italian suede snap jacket
from Todd Snyder

Todd Snyder Dylan Italian Suede Snap Jacket

Dylan Italian suede
snap jacket from
Todd Snyder

Layer Up With
a Jacket

It's the subtle difference between merely being clothed and “getting dressed.” The right jacket can make an otherwise simple outfit look outstanding. If you favor clean lines and classic styles, this will help you turn it up a bit. A plain turtleneck gets a monochromatic boost with the addition of a bomber. Your average T-shirt and jeans get instantly elevated by a simple chore coat or luxe suede jacket. And a pair of chinos, fatigue pants or dress trousers suddenly look much cooler when paired with a worn-in denim trucker.

Experiment With Colors

Most men have a color or two that they lean towards when shopping. You find a shirt you like, pull the navy one and when you get home, you hang it in the closet with the other shirts in a near-identical shade of dark blue. Sound familiar? It's a safe approach—you know what you look and feel good in, but it can get boring. Try experimenting with new shades. If you wear a lot of blue, try an olive green which pairs nicely. Or if you've got a lot of browns and tans, opt for pink or purple which go great with earth tones. And if stronger colors feel a bit too bold, ease into things by incorporating more patterns in neutral shades.


Paraboot Michael Leather Derby

Michael leather derby
from Paraboot

Funkify Your Footwear

Classic sneakers will always be in fashion. So will sophisticated dress shoes. But there's something to be said about the wild options stylish men are sporting these days. From chunky-soled loafers and hardy Tyrolean-style lace-ups to laidback suede mules and slip-ons. Even the most simple outfits get an unexpected boost from grounding the look with some unexpected and interesting shoes. The overall result is at once effortless and considered, rather than strait-laced and run-of-the-mill.

Break Out With Texture

There's no reason why even your off-duty outfits shouldn't pack a punch, right? We are of the view that good style never takes a day off. And texture makes everything a bit more interesting. There's something about unique, textured fabrics that makes even the simplest of outfits look cool and considered. Incorporating a texture instantly makes it look like you spent a lot of time putting your look together. Try on a shaggy cardigan, corduroy pant or some shearling/fleece outerwear.

Go Wild on Vacation

Curious about switching up your style? Traveling is the perfect time to test-drive fashions that you're interested in but maybe don't have the courage to wear in your everyday life yet. You're already stepping out of your comfort zone when you're away from home, and no one in this foreign place knows what you usually look like. So pull on a few fresh styles and see if you like it. By the time you get home, you'll be much more comfortable and thus much more confident.


A 2015 study revealed that students who considered themselves more formally dressed than their peers were more likely to engage in abstract thinking and more likely to reach their long-term goals.