Help Me Dress Myself: Changing Your Look (Without Being Obvious)

Stylist Jessica Chance shows us how to update our day-to-day look without it being too noticeable.

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Are you one of those guys who wants to look stylish but finds it doesn’t come all that naturally? We feel you. Don’t fret: With some advice from Jessica Chance, men’s stylist at Rag & Bone and menswear blogger, we’re all going to learn how to dress a little better. In this edition, we’ll be looking at how to subtly change up the day-to-day button-down, jeans and sneakers wardrobe that you’ve grown tired of, without drawing too much attention to it.

Step #1: Wear Button-Downs Sparingly

Because it’s the go-to office shirt, wearing button-downs every single day is something many men end up doing. And according to Chance, changing your look doesn’t have to mean sacrificing the professional aura (and ease of dressing) that comes with that. “Swap in a dark-colored crew neck t-shirt with a bomber jacket every once in awhile, or throw on a henley rather than a button-down,” she says. “One of my favorite at-work combinations is a dark grey henley with a black chino.” Yay for fewer broken buttons!

Step #2: Rotate Your Pant Styles

Rather than wearing the same pair of jeans for the rest of your days, Chance suggests adding a little incognito versatility to your wardrobe by flip-flopping between pant styles every other day of the week. “For guys who get caught up wearing only jeans, I recommend adding a pair of chinos into the mix every other day. You’ll still have that casual, going-to-work vibe about you on those days, but you’ll also have a completely new and different look.”

Step #3: If Jeans Are Your One and Only, Buy a New Pair

If the thought of wearing anything other than jeans has you out of your comfort zone, don’t stress: Chance says revamping your look is as simple as buying some new denim. “If you’ve always worn blue jeans, try on a pair of black jeans. And if you’re attached to one style in particular, I still recommend purchasing a new pair—it will fit better, the color won’t be so faded and it won’t look dingy. Hell, I see guys buy five pairs of the same exact jean all the time for that exact reason.” We know saying goodbye to your favorite old blues isn’t easy, but trust us, it’s what they would have wanted.

Step #4: Find Yourself a New Jacket Every Year

One of the simplest ways to add variety to your wardrobe without having to put in a whole lot of effort is to pick up a new coat or jacket each year. “We all tend to wear the same old jacket every single year because it’s our favorite jacket, but in reality, it’s probably dingy and out of style,” Chance says. “If you really love that style, look for an updated version of that jacket. I’ll bet you can find one in a different color that fits better and adds a noticeable, but not too noticeable, change to your look.”

Step #5: Own Multiple Pairs Of Shoes

For being perhaps the most overlooked aspect of many men’s outfits, shoes are a surprisingly easy way to add a little flair to your look. Chance recommends designating a different pair for each of your daily activities: “You know you need to buy another pair of shoes when you’re going running in the same shoes you’re wearing to work. Having a pair of athletic shoes for running, a somewhat nice pair of sneakers to wear to work, and a fancier leather shoe for formal events will help you add versatility to your everyday look, without having to put in a bunch of effort.”

If you have any questions about getting the look you want—fits, cuts, colors or anything else fashion-related—email us at bm@dollarshaveclub.com. We’ll have Jessica answer it in an upcoming post.