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sharp dressed plan
how i got the boot. and contemplated the jacket and tie.
by adam kraemer (@DryWryBred)

I have been of the mind, for a while, that many men tend to reach an age where they basically stop caring about what they look like in public. As near as I can tell, it's somewhere around 50 and it's at least partly based on whether or not they're married.

Now I'm not saying that they start going to work in their bathrobes or stop shaving before going to dinner with friends. But they don't quite pay attention to things like well-groomed hair, keeping their belts at the waistline, or not wearing socks with sandals. Part of it is that we all, as we get older, tend to be more set in our ways. This is true for both men and women, but somehow women tend to try to remain stylish, even into their 80s and 90s, while men, if they're not suffering a midlife crisis or the end of their first marriage, tend to get stuck in some sort of combination of what was in fashion the last time they cared about that kind of thing, what they find comfortable, and what their wives pick out for them.

There's a noticeably interesting trend right now, in fact, as the baby boomers of my parents' generation start making the transition from midlife to senior citizen age. Even just 15 years ago, it would have been strange to see men with gray hair wearing blue jeans and sneakers. At least not a decent pair of blue jeans - with the original cuff. (What's up with that, by the way? Is there some sort of elderly person's store that only sells jeans in measurements of, say, 34x40, forcing them to all be shortened in Singer sewing machines from 1978?) However, all the kids that grew up in the '50s and '60s, wearing jeans and sneakers, are now, if I do my math correctly, all turning 70 this year. Every single one of them. And many are still wearing jeans and sneakers.

I bring all of this up because we've had a lot of snow in New York this winter, and are expecting a bunch more between now and our allotted 12 days of spring before the temperature hits 90 and stays there for the summer.

Okay, maybe that mental leap isn't so clear to someone who's not reading my mind.

So for all of you who aren't Liam, the invisible psychic tuna who lives in my kitchen, maybe a little more insight into my thought process is necessary. Essentially, and I actually posted about this on Facebook last week, I came to the conclusion during our last snow/freezing rain/sleet/bagel day that my boots were pretty much useless for anything more treacherous than walking around my apartment. And even then, only staying on the rugs.

However, when I tried to Google "fashionable men's boots," in an attempt to get an idea of what styles were available for a 36-year-old single male (me), I was disappointed in more than a couple of ways. A few sites, it turned out, were just really shilling for one company. Another site suggested I try UGGs for men, which I wouldn't have done anyway, as they're not waterproof and I'm not gay, but it turned out the article was written in 2004, so that really missed the point. Another site showed a number of great pairs of boots, none of which sold for less than $300. If I had $300 to spend on boots, I'd spend it on a flat-screen TV.

I then decided to open it up to a forum of my friends (hence the Facebook post), who actually gave me some pretty great advice, most of which I couldn't take, largely because it would have required buying at least 7 different pairs of boots. I was aided in limiting my options by deciding only to shop in my neighborhood, which pretty much meant either Payless or Fabco. This was not a deliberate move to narrow down my selection or save money, but, rather, an attempt to not have to walk more than two blocks away from my apartment. Not that I mind saving money by not buying name-brand, but the boots really need to last at least through this coming Thursday, which, judging by previous purchases at these two stores, I have about an 87% of happening.

Another plus (and don't worry; I'm still bringing the topic back around) for my boot selection process is that I wear jeans to work every day (as do a large percentage of my coworkers; don't worry, mom, I'm not dressing too casually for the office). I've found this to be pretty much the norm in the advertising industry among people who don't tend to have face time with the clients. I realized this was useful when my friend Dan replied to my post with "I have a pair of L.L.Bean allegedly waterproof hiking boots that have served me well this winter. They look a little funny with a suit, though." Dan's a lawyer, however, which means a) his work requires him to wear a suit and b) I can't be sure if he was telling me the truth.

In the end, I settled on a pair of Timberland-style work boots (affectionately known as "shit-kickers"), but in a darker brown than the classic tan work boot. In choosing these boots, I opted not to go with my other readily available options - the classic duck boot, the oddly-named wolverine boot, the ankle-high suede boot, or, as I mentioned above, the men's UGG. My new boots are comfortable, they're waterproof, they have non-skid soles, and they look pretty good with blue or black jeans (I've been playing on and off with a metal band recently and black seems to be the required uniform). They slightly resemble Doc Martens, but I can wear them without the need to fake angst or be 23 years old.

Which - I told you it was coming - brings me back to the topic of dressing for your age. Or, more importantly, dressing for my age, a skill with which I sometimes have difficulty. The problem is that, as a single 36-year-old male, there are a number of criteria (criterions?) that need to be taken into account when choosing any article of clothing for my wardrobe. I want it to be reasonably fashionable. I want it to be flattering. I want it to not repel women, and, in most cases, attract them. I want it to fit within my budget. And, if possible, I want it to be made out of a space-age polymer that allows me to block my thoughts from Liam.

Mostly, though, I want it to be age-appropriate, which can be tough. Despite some gray in my beard, I'm not my father's generation (as that would be, by definition, pretty much impossible). I still want to look as though I'm somewhat dialed into what's hip (not sure if the word "hip" is hip, though). Which isn't to say my father's a bad dresser. Outside of the waaaaay too short shorts he prefers to wear (we had a conversation about this last summer; he just likes them, but it does mean he's less cool in this instance than my step-grandfather who has begun wearing cargo shorts), his clothing choices don't generally leave a lot to be desired. But at his point in life, "chic" probably isn't a word he'd use when describing his preferences to a given salesperson. Not necessarily a word I'd use, either, but that's in part because I always feel I'm pronouncing it wrong. That and "niche."

I also don't want to dress like today's teens or even today's college students. When a man my age does that, it tends to be, at best, sad and, at worst, creepy. Not that I'm totally sure what exactly today's college students dress like anyway. I'm under the impression that it's probably extra-tight jeans and Converse All-Stars (I do own a pair of the latter), but that's based solely on nearly no observation of college students whatsoever. I'm actually more dialed into what my nieces are wearing, and the oldest one is 3. I know I'd look really silly in Baby Gap clothes for girls. I'm pretty sure I would, anyway.

It has gotten me thinking, though: since I'm definitely an adult (mostly), where do I turn to find a style that says, "You can take me seriously, even if I'm not wearing a tie." Because an editor wearing a tie in most ad agencies generally says either you're heading to a funeral or you have a date that night. Or you've got a job interview and don't care if everyone knows it.

So I've started turning to men's magazines. I'm a subscriber to Esquire; they have a whole fashion section every month. And a fashion issue once a year, I think. I also had a subscription to Time Out New York, but that only told me how to dress if I were a female sculptor from Brooklyn or a transvestite club promoter. Surprisingly similar outfits, by the way.

I've also perused GQ, considering myself to be somewhat of a gentleman, but I find their fashion stuff a little too avant garde. The first listing on the 188-slide presentation on their Web site for example: "The black velvet collar evening coat with a black bow tie and a briefcase." I'm almost more likely to wear Baby Gap. "The subtle and super-cool shirts and ties under the suits.... Lanvin really knows their customer and he is a well-dressed, refined man." I live in Queens.

Back to Esquire, then. I find most of the stuff in their fashion section, when it's not, um, hipsterish, to be mostly up my alley. I'll put it this way - my senior year in college, probably about a third of my wardrobe came from Structure, and might still, if they hadn't been rebranded. I do have a bit of a bone to pick with these men's magazines in general, though, Esquire included. I don't quite understand why they are compelled to offer the most expensive versions of whatever they're highlighting. I get that they like to go with the designer clothing, fine, and then leave the rest of us to find the affordable versions of those clothes. That's okay for tailored blazers, custom shoes, high-end watches. However, to take a random example from this month's issue, "cotton tank top ($98) from Dries Van Noten."

I'm sorry, cotton tank top ($98)? Now, I'll admit to being totally ignorant of Dries Van Noten. I don't even know if that's a man or a woman. But I have seen, over the years, a bunch of cotton tank tops. Not a single one of them inspired me to say to myself (or telepathically to Liam), "Yeah, I'd pay $98 for that." More to the point, how many readers of Esquire are likely to run to their local Dries Van Noten outpost (???) to pick up a 3-pack (I assume they come in 3-packs, like Hanes) of tank tops? If I had $300 to spend on tank tops, I'd spend it on a flat-screen TV.

I get that they just had to have the leather braided belt by Gucci ($385) and the wool cardigan by Dolce & Gabbana ($1,045), but nearly a hundred dollars for a tank top? That had better at least be preshrunk cotton, all I'm saying.

I do digress, however. The point is that maybe the men's magazines have it right for me. Maybe at 36, with no wife on the immediate horizon to pick out my clothing for me and allow me to forget to comb my hair, I'm finally at the stage where I wouldn't feel as though I were somehow pretending were I to buy some of those outfits (or their less expensive counterparts, to be exact) and dressed like an adult (or is that as an adult? Whatever). Not that I'm losing my jeans and button-downs any time soon. But every now and then, maybe you'll see me with a shirt and tie under a sweater. Or a sweater under a blazer. I think I'm old enough.

But, you know, not too old.


A native of Elkins Park, PA, Adam Kraemer spends way too much of his time repeating "K-R-A-E..." He moved to New York City in 1998 and earned Master's in Journalism at NYU; don't let his writing fool you. He feels he is best known for saying the things no one is thinking, but afterwards wish they had been. He spends his free time wondering where all his free time goes and why he can never come up with a decent kicker for the ends of his articles.

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lisa r
2.7.11 @ 10:55a

My dad still has to get clothing approval from my mom. As a result, he's always presentable and never caught outside in an undershirt or the wrong color socks with his shorts.

adam kraemer
2.8.11 @ 11:59a

I actually just discovered my favorite thing about the new boots - they don't squeak. My last pair actually used to squeak on the carpeting in my office. I didn't even know that was possible.

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