Ask dapperQ: Dressing Like an Adult?

A reader asks:

” I am trying to get a hold on my own style, always having been plagued by a strong desire to look and dress like a teenage boy from the mid ’90s. If left to my own devices, I would wear nothing but baggy jeans, flannel, and beat up baseball caps…I am 36, and I’m a teacher at a pretty casual, friendly high school. My fallback for work has always been dark jeans and docs and button downs (in the winter, add a pullover over the button-down). That’s pretty much what I wear every day. I would love to lighten my style a little bit and add some more dapper or fashionable pieces, but I am afraid of coming across as trying to look too much like my students. I like being 36, and I’m not wishing for my 20s – and I want to look like an adult. For instance, I see a lot of Converse and/or Vans in the pictures on your site, but I’m always afraid to purchase any for fear of looking foolish…Do you have any suggestions for ways I can finally enter the 2010s as an adult?”

I’m going to dissect your question to ensure that I (try) to address all of your concerns. Let’s discuss age first. I live in New York City and us urban folk do not consider 36 to be very old. Our city, like similar metropolitan areas, is filled with vibrant, stylish artists, designers, business professionals, academics, musicians, models, actors, writers, nightlife socialites, you name it. And, people do not give up expressing themselves via their own personal fashion styles once they hit 30+. Yes, some people may tweak their styles a bit in order to reflect their inner growth, new tastes, or new work responsibilities. For example, you may still own a vintage Nirvana or other fill-in-the-blank band t-shirt. I’m talking about a REAL one, not those mass produced faux-vintage t-shirts at department stores. And, you have the right to still rock it because you were actually old enough to go to one of their concerts.

So, maybe you won’t pair your vintage t-shirt with the now- too-small pair of skater shorts you once wore. But, mix it with a nice pair of tailored jeans and a blazer or a leather jacket for a day of grading papers at the coffee shop, and you’ll be “age appropriate” casual cool. The point is, your body is a canvas for your personal style, and your style should represent your inner self. While you may be different now from when you were 20, there are still parts of you that are the same, and your style can express all aspects of your being.

Oh gawd, I think I just sounded like an adult! Second topic, quick. Sneakers. Converse, Vans, and sneakers in general as “grown up” attire for the 30, 40, 50+ set? Of course! Ellen and Maddow do it.

And, if canvas doesn’t float your boat, many brands carry more dapper leather and tweed styles as well. Take for instance…

Vans OTW Tweed Pritchcard

AR SRPLS X Converse Pro Leather

In GQ’s recent article, The Young Man’s Guide to Geezer Style, Will Welch writes, “Right now, the cool kids aren’t taking their style inspiration from icons like the Clash or the Stones or the Kanyes. Nope, they’re adopting the suited nonchalance of old grandpas, from their fusty ties to their sneakered feet.” He goes on to say that “geezers” know that sneakers go with EVERYTHING and are stylish and comfortable.

via GQ

Ultimately, polished, more “tailored” looks are key to pulling off a dapper sneaker ensemble. For example, take a look at fashion blogger Dustin Tyler Moore’s sexy grown sneaker style via Closet Freaks.

Dustin Tyler Moore via Closet Freaks

We’ll close with the toughest part of your question: finding personal style. It is hard for me to give you specific recommendations without knowing you – what makes you tick, what inspires you. Do you like American clean and classic? Southern dandy? Urban hipster? Ivy League dapper? Eclectic? Rugged? I would first start by reading How to Find and Refine Your Personal Style and then move onto finding inspiration from our Seven Days of Dapper, He Said/We Said, and Style Icons features. You can also find a treasure trove of ideas from menswear blogs like Closet Freaks (especially their incredibly helpful video on fall style) Dapper Lou, Street Etiquette, Brooklyn Circus, The Style Blogger (especially the 25 essentials list), etc.