The To-Do List: Setting Goals and Meeting Them

I was sorting through some old drafts and documents on my computer the other day and ran across an old list of sartorial goals. I was originally going to write a post based on this list when I first wrote it, pointing out that, while I'm here dispensing advice to you folks, I have a lot of improvements I want to make myself. The article never really came into fruition, and I honestly kind of forgot about the 'to-do' list that I had made. Stumbling upon it again now, it's actually really encouraging, because, for the most part, even without looking at it every day, I lived up to my goals and can cross most of these items off:

• Tie a good tie with a strong dimple at the right length in less than 20 minutes. - Boom. I've got my tie-tying down to an art. I actually had one of my best friends come visit the other week, and we got all inebriated and had a tie-the-knot drinking game/contest (at 2 in the morning on a Tuesday, much to my girlfriend's dismay). I have some awesome and ridiculous pictures from the night, which I'll share someday.

• Don't somehow, mysteriously, fuck up my shoes every time I wear them on things like, no joke, cracks in the sidewalk. - This one I honestly still struggle with, haha, but I'm not exactly sure how to work on it. I will say that, in general, as I've dressed better and better, I've really noticed myself moving with more care and purpose. I think I can safely say that I'm a generally less sloppy person, in large part because it's hard enough to afford to buy clothes (and shoes) once, let alone replace them because of my own damn clumsiness. So, I'm gonna call this one a win too.

• Don't get stuck on one outfit that worked really great, and then wear it over and over. - Another one I think I pass with flying colors. In fact, I may have taken this into problem territory on the other end of the spectrum. Instead of struggling with wearing the same things, I struggle with a need to wear something new or different every day, whether it's a whole new piece or even just a new combination, and it's become a bit of an insecurity in it's own regard. Brian Sacawa  of He Spoke Style started his own blog with the idea of wearing a 'uniform' every day for a year, and I think that challenge takes a whole different level of confidence.  

• Find a really good fitting jean. - I give myself a half-check on this goal. I've gotten a better fitting jean, but still don't have that one, high-quality, perfect-fitting piece of denim that denim-heads tend to gush over. I'm giving myself a pass though...I purposefully held off on this all summer just waiting for the weather to cool down a bit so I could justify buying some mid-weight denim that isn't really hot-as-sin-and-humid-as-all-getout compatible. Now that the temps are cooler, as soon as my bank account can handle it I'll be grabbing pair, probably from Gustin or Dyer and Jenkins.

• Find a great tailor and build a relationship with him. - Alas, I can't really check this bad boy off the list, which is sad, because it's probably the most important item on here. Like I say all the time, fit is everything, and a tailor is the best way to get that perfect fit on every item of clothing you wear. Right now, I'm struggling with Chicago's selection of tailors...too many expensive options that get less-than-desirable reviews. Unfortunately, I don't have the spare funds (or clothing) to really dive into the trial-and-error fiasco that finding a solid tailor can be. The Peter Field seamstress gets my whole-hearted endorsement for alterations like taking in a shirt, and I have a last-ditch high end fella that I take more complicated work to if need be, but I still am looking for someone to fill that middle ground.

• Wear a blazer/jacket on a daily basis (and not just for warmth). - When I first started taking my daily wear to the next level, I limited myself to shirts and ties, and really only threw a blazer on as an extra layer in colder months. I'm proud to say that I am now comfortable wearing a blazer on a day-to-day basis as a part of my basic outfit. I honestly think I've actually evolved sartorially past this step by recognizing that nothing should be an every-day-no-matter-what necessity, and instead dress on a day-to-day, by-the-occasion basis. Happily though, these days this involves a blazer more often than not.

• Wear pocket squares (with confidence). - Man, I was so very timid when first stepping into the pocket-square game, and unnecessarily so. I now have a small but decent selection and try to wear one as often as I wear a blazer. I've even started experimenting with throwing them into less formal outfits, tossing one in the back pocket of my pants, or the breast pocket of a shirt or casual jacket. Instead of being an element that makes me nervous and hesitant, I now accessorize with confidence.

The whole point: not only is it great to have a list of goals to pursue, it's also great to recognize when you've achieved some of those goals and allow yourself a good pat on the back. Now it's time for me to create a new list, tuck it away somewhere for a few months, and see if I live up to my own aspirations and expectations. I'll keep you posted.