stylish daily dressing: challenges, hacks, rules to live by

Style isn’t easy. It requires constant attention. And practice.

Some people make it look effortless, and let me set the record straight, those people are conscious of it just as much as those who maybe struggle more with their end result.

Stylish folks of Tampa

There are so few sartorial assumptions that are fail-safe, and yet, when an outfit jives, it shines.

Style isn’t the same as trendy. Trends are for the mass market; they’re forgettable. Who wants to be forgettable?

After a week’s worth of gold Apple iPhone 6 Facebook postings, the color I was going to get and be unique(!), I’ve decided that style is also about balance: going against the grain, choosing something unique, and getting what your heart desires, regardless of the former two elements.

Technology isn’t the same as fashion, but they are growing closer, largely thanks to the industrial design innovations of Apple, and its retail distribution strategy different from previous technology models.

As I age and focus more on who and what I am/like/desire out of life, I realize that it isn’t wealth, it’s style. I don’t desire great accumulation, especially of anonymous interchangeable objects. Instead, I want quality, precision, and uniqueness. Those elements make style, and beauty.

A typical outfit for me: white, gray, or black tee, Nike cap, tortoise shades

Style says you strive for clothing that reflects your values as a person. They don’t overshadow your personality, but rather complement how you are perceived by others.

Style also requires confidence. There are pieces that appeal to me but I say “I couldn’t pull that off.” Really, anyone can pull anything off, you just have to believe in yourself, and embrace the fraternity mantra “fake it ’til you make it.”

I am always impressed by key figures in my life who toe the line of edgy, avant-garde dressing regularly, and do it without looking completely ridiculous. That isn’t to say they don’t make mistakes, or misjudge their ability to eschew conventions.

A staple of my closet and statement piece: Tod’s black patent leather gommino drivers

I’ve also found that the relationship between price and style is not constant. Wearables fall all over that spectrum. I do think that an above-average budget inevitably steers you toward higher quality fabrics, more thoughtful cuts, and presumably, items with longevity.

I have been buying, altering, and wearing a lot of new stuff lately, and have had to remind myself of some core values I try to stick to when buying/dressing/styling myself or others:

Fit is probably the most important factor, in how you look, how you feel, and how attached you become to a piece. I invest in alterations. They’re not cheap, but if it means you feel more confident and wear an item more, why wouldn’t you?

Fit and general quality missteps are unavoidable, but can be reduced with careful vetting of your favorite brands, and with a good tailor’s phone number.

Another typical outfit: polo shirt, slim-fit shorts, accessories

There are staples, and there are statement pieces. They aren’t always the same, or mutually exclusive. Having very nice basics, that complete a look without adding clutter to it, is important. However, doesn’t hurt to tweak one element of those basics, like a color, fabric, or include some other quirk.

Your gut will tell you. Your brain will trick you. There are things one reacts to involuntarily, either as a must-have, or not-so-must-have. Then there’s everything in between. Taking into account a sale or discount…those confuse the situation. A steal should not be overlooked, but it should first and foremost be something you like, and would wear even it wasn’t on sale.

Latest in a series of selfies taken at the Oxford Exchange

Keep a running list of needs, wants, and anytime splurges. I find a million white, black, and gray t-shirts I like. Do I need them all? Definitely not. Do I need new jeans? Yes, and it’s becoming a real issue (expanding legs, butt). So jeans are on my needs list, as are new loafers because one pair I have is ripping apart slowly, and the other is starting to smell.

Wants: a leather portfolio pouch, a new tote bag. Anytime splurge: anything on my ShopStyle favorites list that goes on sale.

Woe is me, baby tee!

I prefer to shop alone. With other people, I get easily talked into purchases that I otherwise might not make. Some duos work very well shopping in tandem. I trust myself and don’t usually need a second opinion. Just be aware of the power of peer pressure if you do go with some pals.

Pay for dry-cleaning and make your clothes last longer. I can be excessive, taking my t-shirts and shorts to the dry cleaner, but they come back so pretty and pressed! Balance the cost of this service with giving your clothing a break from the comparatively rough spin cycle. And since you’re dropping a hefty dolla, you can specify treatments — starch, pressing, whether shorts are pinned or clipped to the hanger (I get mine clipped).

A special Gant Rugger button-down I have gotten plenty of mileage out of

Texture matters. It creates visual interest. I’m amazed at how many variations of 100% cotton one can have with varied treatments and weaving techniques. I wrote this article a while back about fabrics.

I hate contrast stitching. It’s visual overload.

Style is conscious. Did you know Urban Outfitters has a history of uncool management practices and philosophies? Avoid!

Style is local. Support your neighbors, friends, and folks with passion. And, dress for your environment.

Style is interpersonal. Shop with people you know, like, and trust, wherever possible.  They’ll help you and will feel invested in your look.

Two cherished once-used wallets: Louis Vuitton monogram glace and Tod’s bright mandarin orange card case

Style is messy. This is the bottom line. Style is fluid, an ever-elusive moving target. Clothing and accessories come and go, wear out, or become damaged. You lose things. This is all fine. Just as long as you continue to cherish, but fearlessly enjoy, what you do have, and make additions to your closet that speak to the consistent thread that is your style.

Regardless of what you’re wearing, people will recognize that.