How Not To Dress Like Your Grandfather

I was recently contacted by a young gentleman in Sweden who asked that I help him with his style of dress.

This 25 year-old man is drawn to a very classic clothing; so much so, that his friends felt he dressed like an old man. “You need to dress for your age,” they said. Black, all black, was the recommendation.

Preferring East Coast Ivy League sensibilities, this sharp fellow contacted Off The Cuff for some advice.

Let me just say up front that my Swedish friend has made some changes to his style and now presents a truer, age-appropriate classic version of himself, as the lead-off image above shows (yes, that’s really him).

“You see, I feel like I’m stuck in a rut. I’ve always tended to dress classically. I’m quite the fan of British clothing and the Ivy League look. But, I also like the boldness (and in many cases perfect simplicity) of the Italian way of dressing. And I almost never wear black.”

“My main concern is that lately, especially the last couple of years during the fall; I’ve become more experimental than ever when it comes to colours and patterns. This has made for a very, shall we say, busy look, from time to time. Also, I’ve become narrower in my way of dressing. I feel extremely casual even with a dress shirt, chinos and a v-neck or crew neck. Almost like I need a jacket to feel properly dressed. This has generated looks that have made me look very, very old. And not in a good way, I’m afraid.”

“Today for instance, I wore khaki coloured chords (which have stretched out to become quite baggy), a white OCBD, an olive v-neck, a brown tweed jacket with suede elbow patches, suede Chelsea boots and a bright orange paisley tie. This outfit combined with my somewhat hefty body made for a really old look.”

This is actually a common problem I tend to see in certain Trad/Ivy League aficionados. In their zeal to capture the truest essence of “preppy,” they wind up making caricatures of themselves.

The outfit described above is about as grandfatherly as one can get. While the individual components are quite stylish on their own, together an old, heavy look is created – very much at odds with my reader.

Don’t overdo it in your effort to look classic.

Instead of emulating an entire “look,” be yourself and highlight one or two key wardrobe elements like a blazer or a good pair of wingtips. Pair the key piece with something you already have. Try the hi/low approach: wear the good blue blazer with your favorite classic cut jeans, white oxford and those great wingtips.

Updated: Blazer with oxford & jeans

“I also often wear ties and never put a jacket on without stuffing down a pocket square in my pocket. During summer I seem to loosen up a bit by default, moving to lightweight chinos, Bermuda, OCBDs and polos, topsiders and plimsols.”

“My female friends are constantly nagging about how I should stop dressing like a 65 year old. They go on and on about how my way of dressing ruins my ‘wild years as a single young guy’. And while my male friends do think I dress very well, bold/cool etc, they also think it can get a little to stuffy and uptight, to the point where they feel a little uncomfortable.”

“The general tips I get from my female friends are: embrace black, wear mostly jeans and t-shirts. If you must wear a jacket, wear a black suit jackets and never ever wear a pocket square. And stick to black shoes or sneakers.”

“I really don’t want to go there, still, I find myself looking at many of my friends in jeans, sneakers and simple shirts, thinking they look great. I just feel too casual and to undressed when putting something similar on.”

Personally, I think the issue has a bit more to do with personality than just clothing. He can certainly dress in a classic, East Coast preppy manner but do so in a younger frame of mind. My own take on this philosophy can be found in my “College Professor” column.

In some cases (actually most cases), it is just fine to lose the tie in favor of a pocket square. He could get newer cords or chinos in a trimmer cut that is still comfortable and try trousers with a higher rise and slightly trimmer leg. The same holds true for sweaters, v-neck or crew neck. He can try some more fitted fine-gauge merino sweaters. Not snug, but not baggy.

The merino wool itself is less bulky and will help to give a more modern, less slouchy look. Additionally, this kind of sweater works better in warmer weather when a extra layer is needed.

My reader can also try and create a more coordinated color palate. A tie or pocket square can be used as the shot of color, but it is better let the major wardrobe pieces be the foundation upon which it rests. One can also do this with a brightly colored or patterned jacket. Just make a point to choose one item as your “message” and let everything else step a back a bit and ground it.

An OTC favorite brand, J. Crew (unfortunately not yet available in Sweden) does a great job with this kind of look. Use its examples for inspiration, not necessarily as a literal guide. Their designers do an excellent job updating classic garments for modern style.

Modern & Classic (Sartorialist)

So yes, trust your gut and stick with your own style, but look at yourself with a younger eye. Remember that what we see today as “classic “ preppy and Ivy League dress was, at the time a radical and iconoclastic departure from proper dressing.

The goal for those kids was to take the formal prep school and college uniform and make it their own, to personalize and update it. So interpreting and updating that style for modern life today is really paying it homage.