How to Up Your Style Game Without Looking Like an Old Man

Tailored blazers and suits are great because they’re flattering and can therefore boost your confidence. As you find brands that fit and begin to wear more tailored clothing, however, one pitfall is they can make you look older, and not in a good way. You want to look sophisticated and mature—not like a grandpa. So how do you up your style game without looking like an old man? Here are some tips. It all comes down to fabric, fit, and design.

Wear dark colors in subtle textures

Fuzzier and plush fabrics in drab colors is what comes to mind when I think of grandpa—corduroy and tweeds in muddy earth tones. While those fabrics and colors can be worn in a youthful way, one simple thing you can do to veer away from old man connotations is to wear darker colors in fabrics with interesting surface texture you can only really detect up close. Navy, charcoal, or dark brown even; dark colors are flattering and provide contrast against lighter shirts and pants; or with a darker tonal fit can look great for an evening out. By going for subtler surface texture—hopsack wool or small patterns like puppy tooth, for instance—you avoid the extremes of either overly plush (grandpa) or chintzy and shiny.

Stick with cutaway and spread collars

I love the OCBD. It’s an all time classic American shirt. But here’s the thing: It’s kind of frumpy. The oxford cloth can look dingy in the normal range of colors it’s made; the collar has been ruined by heavy, stiff linings in ubiquitous Cintas plant manager uniforms; the fit is typically boxy. One reason I’ve spent so much time and money on so many OCBDs from so many makers is just trying to buy one that feels cool and breaks free from some of those connotations. And while I can appreciate the heritage of even the frumpiest ones, if you’re trying to avoid an old man look, here’s my simplest advice: just wear a wide spread or cutaway collar.

If you’re wearing it open-collar no tie, go cutaway. If you plan to wear a tie a reasonable percentage of the time, medium-wide-spread. The normal, more business-y fabrics like broadcloth, pinpoint, or end-on-end are all great (I like light blue and white, plain and in stripe configurations, particularly reverse stripes). Those can look great even with jeans, given you wear a layer on top, whether that be a blazer, sweater, or some type of outerwear (bomber, chore coat, peacoat, etc.). Also give faded indigo shirts in chambray or denim a try like what you can get from Proper Cloth or Spier & Mackay; those have interesting surface texture, pair well with dark or white jeans, but can also dress down an outfit with tailored pants.

Get things tailored to fit

I like a little bit of drape in my tailored clothing—a slightly swelled chest, slightly wider shoulders, some room in the thighs and seat of my pants to hang well—but always fitted to give some shape to it. A nipped waist in the jacket, a tapered cut in the pants. Many jackets—particularly American ones—fit boxy. Combined with low-cut armholes and baggy sleeves, it creates an overall frumpy look. This is why I recommend brands like SuitSupply, Spier & Mackay or Natalino on the more affordable end and the No Man Walks Alone x Carrara line, Ring Jacket and Anglo-Italian on the higher end. They’re either made in Italy where the art of a well cut armhole and sleeve is still in active use, or inspired by the Italian cut and made to match it. The only mainstream American brand I can think of that does a good job of this is Ralph Lauren, but only in their Polo line and better. The Ralph RL or Lauren RL lines found at department stores are garbage that fit terribly.

A slim-straight or tapered pant silhouette is part of this, too. Depending on your body shape, it can be tough to find pants that fit you well and are flattering. I personally feel that way with my physique, so once I found a company (Spier & Mackay) that made pants I liked on me, I’ve run with them. For tailored pants the fit will be looser by default—super slim wool dress pants are weird and not flattering; they need to drape. But for chinos, denim/five-pockets and other casual pants, a more tapered, fitted look is fine. Just avoid the carrot stick shape created when your hem is too narrow. And don’t be afraid of stretch—my most-worn pair of jeans right now are ultra stretchy slim-straight jeans from American Eagle, that cheapo mall brand. They let you sit properly, lunge deep if you need to and will save your back.

Get jackets that work well with denim

Just throwing this advice out there is tricky because what exactly works well with denim is a huge topic going both directions—not only what jackets look natural paired with jeans, but also what jeans look good worn with a jacket—but I must because our contemporary world makes a full blown tailored outfit look a little out of place in many contexts. A buddy of mine started a new job recently in a casual workplace, and he explained how he prefers wearing a blazer because it’s flattering and he feels more confident wearing one. But he gets comments every single day about being dressed up, despite dressing it down with jeans and desert boots. So a tailored jacket still does feel dressy to many people, but imagine if my friend were wearing tailored pants with a crease in the front and wingtips instead of jeans and desert boots—he’d be better dressed, in that case, than his company’s founder/CEO.

What makes a jacket pair well with denim is essentially this: 1. Fabrics with a bit of texture, not smooth fabrics like worsted which are typically used for suits. 2. Fabrics in more casual patterns, like plaids, houndstooth, herringbones, etc. (Not that those can’t be suit fabrics, but in larger scale and higher contrast designs they’ll be more at home as jackets on their own). 3. I like softer shouldered, less structured jackets with jeans more than padded, structured ones. That isn’t to say a strong shouldered English jacket in tweed doesn’t look great, but to me the unstructured look is more at home in our contemporary world.

There’s a useful thread over on Styleforum where people post photos and debate jeans/sportcoat pairings here, which is helpful because there are some well dressed people who do the look well you can learn from. I recommend it to see examples of a range of people (not just me) whom you can gain insight from.

As you train your eye to determine what looks good abstractly and on your body in particular, you’ll begin to hone in your own preferences for how much drape looks good but not old-man. Your style game can be improved, and as I like to say, it’ll make you look great, feel cool and be an expression of your personality. Good luck!

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