Welcome To Your First Grown-Ass Outfit: Ruben’s Style Story

Over the years, I have gone through my own style evolution.

I have learned a great deal: what rules to follow, what rules to break, and how style is more than what we wear — it’s self and identity and personal expression. I’ve been fortunate to assist others, too, as they sought ways to match their outsides to their insides. Each of these people has a unique Style Story with something to teach.

Meet Ruben — in his own words. The cartoon is mine.

Style -Story: Ruben, Graduate… Soon to be Kindergarten Teacher


I am all about Cyberpunk; I love Neuromancer and the whole aesthetic. I also love Anime, and for a while, when I was in college, my hair was dyed red like the main character from Outlaw Star.

What works for you about your Style, now?

I wear what’s comfortable, and I don’t have to think about it. It’s simple, it’s not expensive or fancy, and it’s me.

What’s the Story behind your interest in a Style-up?

I still dress pretty much the way I did in high school. But soon, I’ll be interviewing for jobs. It’d be good if I didn’t walk into my interviews in a t-shirt and jeans.

What surprised you during / after the Style-up?

I can’t believe how important shoes are. Since they’re way “down there,” you might think they’re not that significant to an outfit, but they totally are.

Which individual or character’s personal style do you admire?

I am all about Cyberpunk; I love Neuromancer and the whole aesthetic. I also love Anime, and for a while, when I was in college, my hair was dyed red like the main character from Outlaw Star.

Being Styley On a Shoestring Budget

Sweater by Gant. Too expensive to begin with. Way too expensive for a first-year kindergarten teacher.

Sweater by Gant. Too expensive to begin with. Way too expensive for a first-year kindergarten teacher.

J. Crew factory store, clearance. Half the price. Just as cool. Save for later.

J. Crew factory store, clearance. Half the price. Just as cool. Save for later.

While I have already written about the Budget Style-up, Ruben presents us with some interesting challenges and opportunities for clarifying priorities. See, in the Budget Style-up, Jeremy was a 29 year old professional, looking to keep the price-tag low.

But Ruben, a recent graduate, going into early-childhood education, has a different set of needs and restrictions. We needed to find quality pieces, select carefully, take copious photos, and buy the essentials only: anything else wound up as a link in a “some-day” shopping list. When possible, we isolated a “look” and dug up links for cheaper versions to return to in fall, when those first paychecks come in.

The Style-up


Hybrid Casual / Classy: Unstructured Blazer

Hybrid Casual / Classy: Unstructured Blazer

Blazing the Trail Between Casual and Classy: The Unstructured Blazer


Unstructured blazers can be treated like a sweater. Throw in on over a t-shirt and roll up the sleeves!

Before Ruben and I even made it past the first rack (I guess that’s why it’s called Nordstrom Rack. Lots of racks?) we happened upon this blazer.

On the one hand, it looks great, and it would be a useful piece to have in a wardrobe. On the other hand, it serves to teach us a principle which we will return to numerous times in this Style-Story: a great outfit layers a) textures, and b) classiness levels.

The main formula is: a mash-up of classy and casual, high and low, (for a more in-depth look, click here) creates a look that’s both interesting and also balanced.

This jacket, as a case study, has all the formal features of a dress jacket (on the outside, anyway). Lapels, three buttons, the breast pocket, you get the idea.

But the fabric is a lightweight chambray, the red detailing and white contrast buttons add one or two points of flair, and the jacket is unlined and has no shoulder pads (notice how it fits him like a shirt?)

This means he could throw this jacket over a t-shirt and head to the library, to check out activity books for his future kindergarten students, and afterwards, pair it with a white oxford for back-to-school night. It works for coffee with a colleague, and it works for date night.

It also means that it can go over a sweater for cooler months (from what I remember, Boston has plenty of those) and during one of Boston’s charming heat waves, he can roll up the sleeves. Can’t do that with a suit jacket or sportcoat.

Incidentally, if you could use a primer on “how to know if you can roll up your jacket sleeves,” I got your back. And your lapels.

Always start at the ground floor

Always start at the ground floor

As Ruben commented after the Style-up, shoes are foundation of an outfit. Since Ruben’s budget would only allow for one pair, it needed to be something versatile, able to lift a casual look but casual (and comfortable) enough to wear while chasing kids around on a playground.

Three types of shoe caught Ruben’s eye:

1) The Original Penguin Oxford (which you can find on eBay for under $60 – half that if you don’t mind used shoes).

Features to note: the white “Goodyear Welt” stitching is a sign of a higher quality shoe, and the contrast gives it a +1 point of flair in a subtle, classy way.


Boots. Tough and warm…but cool.

2) A pair of boots that seemed like they could stick up for themselves through a sittingBoston winter, still pairing nicely with the outfits we’d soon assemble.

3) The grand-daddy of all classy-casual shoes, Clark’s Original Desert Boots. These “goes with absolutely everything except a black suit” shoes probably win the day. Why? Because Ruben could check his size in the store, and with no trouble, find them newish on eBay for $30-40 dollars.

(This, incidentally, brings us to Shoestring Budget Shopping Pointer #1 — go to a brick-and-mortar store, and try on brands that are easy to find. Choose your size and color in a brick-and-mortar store, and find it later, used! This works best for staples and classics like the Clark’s Desert Boot).


New niche children's book: Denim Connoisseur Visits the Wailing Wall.

New niche children’s book: Denim Connoisseur Visits the Wailing Wall.

No Need for Gourmet Denim

Unless you’re some sort of denim connoisseur, you don’t need to drop a lot of money on jeans, especially if you’re a) a guy, and b) on a strict budget. Stick with Levi’s, get them on sale, and go dark. Indigo. For more on the power of indigo jeans, click here.

As for size, visit a department store or Levi’s store, and try the 511 and 514 first. If they’re too tight, move up from there. Then, note the number and size — and off to find them on eBay for next to nothing.

You’ll notice that at this point, Ruben picked out his jeans, his shoes, and a sweater – but won’t spend a dime until he finds them on the cheap.

Now for the items best bought in the flesh.

Chambray’s Got Your Back

Behold. What not to do. [This, btw, is me before selfies were called selfies, trying to figure out the whole style-thing.]

Behold. What not to do. [This, btw, is me before selfies were called selfies, trying to figure out the whole style-thing.]

Your button-up shirt is the first place where your styliness emerges; while you can get get away with meh shoes and maybe even meh jeans, if your sleeves are poofy and your billowing up over your belt, the look is shot.

This is a problem because manufacturers keep their shirts cheap by offering three sizes: S, M, and L (and maybe an X on each side).

If you’re a big guy with big guns, this is great. But if you are a smaller guy with, like, little guns, you’re gonna find a lot of seriously poofy shirts.

Solution 1: Find a tailor (more on that, here). The up-side? Your shirts will look amazing. The down side? Say goodbye to $40.

Solution 2: Stick with brands made for smaller / younger dudes. Ben Sherman and Express often run a bit smaller. Streetwear brands like VANS run smaller.

Solution 3: Look for slimmer fits in standard brands. Many companies like J.Crew and Gap make a “slim fit” version. When in doubt, try it first.

chambrayarmscrossedLet’s pause, incidentally, for a primer on size-code. Size names like heritage or classic or relaxed fit mean bigger. Names like tailored, or modern fit mean smaller. Don’t worry about the name of the fits. Try the smaller ones first, and move up from there.

Ruben found this great chambray shirt by VANS. It looks sharp and fits well and has two other elements going for it: because it’s chambray, a light blue cloth reminiscent of lightweight denim, it goes with everything.

Classic sneaks like these go with everything - even a chambray shirt and tie!

Classic sneaks like these go with everything – even a chambray shirt and tie!

This also means it can be paired with dress shoes, or with sneakers. For those on a budget, PF Flyers are often less than twenty dollars and they look amazing. (Ruben can teach his future kindergartners that PF Flyers were first produced in the 30’s, which is why they have a classic look. The company was owned by Converse for a while [shocking, given their design], then bought by New Balance in 2003.)

The Magic Blazer

The Magic Blazer

The pièce de résistance: 4 Swappable Ties and a Blazer

Last, in the shoestring Style-up, comes the combo that will allow Ruben to create a week’s worth of outfits: a blazer that will “style up” when paired with a button up, “style down” when paired with a t-shirt, catch eyes – and yet go with everything.

Why a blazer?

First, let me explain what the function of a blazer is; inherently, a blazer is classiness incarnate. It reminds the eye of a suit jacket. So, over a t-shirt, it makes a classy, casual look. Over a shirt-n’-tie, it makes the wearer “dressy.” But it can easily come off for rolling up the sleeves and helping a kindergartener pick Play-doh out of her hair.

Rubin’s dream-blazer retails for way-hay too much money, but on sale, it was within shoestring-reach. It wasn’t cheap, but it’ll be worth it; finding a great blazer can be tricky. It needs to be slim, the shoulders need to fit right, the sleeves need to come to the break in the wrist, and if the fit is off, or the material too Men’s Wearhousey, it looks like your older-brother’s hand-me-down. Unfortunately, there are very few ways to cut corners on a blazer.

Paired with a gingham shirt, knit tie, and cardigan sweater, it's preppy with a side of grunge.

Paired with a gingham shirt, knit tie, and cardigan sweater, it’s preppy with a side of grunge.

However, since Ruben found a blazer with a playful but subtle pattern (see the stripes? Look again…) it was time to pounce.

(This, incidentally, brings us to Shoestring Budget Shopping Pointer #2: when you find a good deal on a hard-to-find piece that will be very useful – splurge. It would be hard for Ruben to find a jacket this fly for this price, again.)

Texture and Classiness Mash-up

Fit aside, the outfits Ruben rocks are no average, “entry level professional clothes” because of the mash-up of these two variables.

For example, the stripes of the blazer play off the stripes of the sweater and the pattern of the shirt. The thicknesses vary, so Ruben doesn’t look like a very stylish zebra. Meanwhile, the knit tie compliments the texture of the jacket in a way that no shiny bar-mizvah tie can.

Speaking of texture and classiness mashup, Ruben found a couple of additional ties that exemplify this style-maneuver. One features a bandana-pattern, but in a thick, quality cotton. One features a loud floral pattern – but in subdued color. To use the “flair-up” equation, either pattern gives him a +1 in flair, but the colors keep it anchored and from being too loud. No “flair-up” there.

Ruben is dressed like a professional, but he’s uncommonly styley. I believe he’ll make an amazing teacher.

The Magic Blazer

A tie – with a bandana pattern?! Yes!

Striking flower pattern - but muted colors. Texture: soft cotton. Awesome.

Striking flower pattern – but muted colors. Texture: soft cotton. Awesome.

This Style-up included:

1 blazer

1 shirt

3 ties

and notes for shoes, jeans, and a shirt,

Shopping the Style-Up Budget way saved Ruben about $400, and that looks good on anyone.

withblazerReady for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A Style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Outside of the Bay Area? Through the miracle of the interwebs, we can arrange an on-line consultation. You’ll end up with a handful of great items, some new looks, and a spring in your step. Click to Email Me.

Want to See More Style-Stories?

Mash It Up: Cold, Warm – Low, High

Cozy top. Cold toes.

Cozy top. Cold toes.

Two equal and opposite rules apply in all areas of the aesthetic.

  • Observe the categories.

  • Mash up the categories.


Wisconsin Captiol Building (Madison) Observes the Categories

Part of what makes this building attractive to the eye, for example, is the purity of the design. To a student of architecture, sure, the neoclassical design contains elements of various historical periods. But to my rather untrained eye,  the constancy, the balance, and the univocality of the building is what pleases my eye.

[That, and the fact that this building is about two blocks from the Great Dane;  this beacon of democracy actually resuscitates fond memories of undergraduate drinking and the eating of too many onion rings.]


The Contemporary Jewish Museum, SF, Mashes Up the Categories

On the other hand, this building, located in my second-favorite city, intentionally blends straight lines with shocking angles. A re-purposed electrical station is mashed up with an avante-garde Borg-like cube.


The Contemporary Jewish Museum’s Western Wing: Resistance is Futile

It’s not as pretty. But it’s more fun to look at. While it’s clear that the first building is a place where committees argue over policies, the second building intrigues us,  makes us wonder what’s inside.

From Buildings to your Style

don draper

When putting an outfit together, you can observe either principal. Honor to the rules, perfectly. That’s what people mean when they say a suit (or someone’s taste) is flawless. He is or she is a vessel for age-old awesomeness to reside within.

Mash It Up

On the other hand, you can mash it up. As I mentioned last week, you can wear a tie to the park. If you do it right.

You can wear a snuggly-looking sweater with summery-looking chinos. fullsizeredpants

sweaterntieredpantsprofileA tie, cut from rough-textured canvas can sport classic, almost stuffy patterns – like paisley.

harris tweedSneakers can be made from Harris Tweed.

And altogether, you get a Libeskind-esque mash-up of old, new, high, low, serious, fun,

And all around awesome.