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  • Writer's pictureEvan Wolkenstein

Style-Up on a Budget: Jeremy M

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

I have learned a great deal: what rules to follow, what rules to break, and how style is more about self and identity and less about cloth and clothes.

I call the process of matching up my outsides to my insides (and maybe stretching both in the process) “Styling-Up.”

“Styling-Up” might be part of someone’s “Style Story” (my nickname for the story that we tell about who we are and how we choose to express ourselves). I’ve been fortunate enough to assist a few in their newest chapters.

As much as I’ve enjoyed the looks on their faces (or their significant others’ faces) as they came out of the dressing room in Styled-Up gear, I’ve found the stories behind the Style-Up to be meaningful and inspirational.

Meet Jeremy – in his own words. The cartoons are mine.

Jeremy M: Sales Executive, San Francisco, 29.


  1. My style has always been very “me.” I do a lot of jeans and t-shirts. It reflects who I am. It’s awesome. But…sometimes it isn’t appropriate.

  2. I can dress up in a suit and a button-up, but it’s very basic. I don’t process accessories.

  3. Essentially, I’m not sure how to make my look “pop.”


My ex-girlfriend used to pick out my clothes. I’m ready for something new.

  1. I’ve gone through a year of transition and many phases. I used to have my clothes picked out for me by my (ex)girlfriend. Since then, I’ve added new clothes, but I’ve been playing it safe. Dress shirts from Target, you know? If I wanted to take a risk – wear a fly suit and stand out – I wouldn’t have known what to do or where to start.


  1. I notice I look forward to chances to show off my new swag. It was fun to get it, but it’s more fun to wear it.


“Ditch” the obese guinea pig and “Charlie” the cat. Childhood tributes to style-icon, Charlie Sheen. #Winning.

  1. Charlie Sheen’s character from Major League – when he pitches? He’s such a bad-ass. As a kid, I had a house-full of pets named after Charlie and his best characters. Especially awesome was the obese guinea-pig named after “Ditch,” the sky-diving instructor from Terminal Velocity.

The Style-Up

Rocking a great look on a budget

To start with, Jeremy and I talked about his budget for the Style-up. It was totally reasonable to accomplish his goals. It was also realistic. This was not going to be a cost-no-matter shopping spree. We decided to do a Style-Up with a budget theme.

For many of us on a budget, the idea of Styling-Up may seem aesthetically appetizing but fiscally impossible. As it turns out, however, whatever you think clothing costs – the reality is that you should only pay about half of that. Think about Nordstrom, for a moment. They have a pretty great range of men’s styles. And they have one price range. Expensive.

Take Nordstrom Rack, on the other hand. That’s where you get Nordstrom’s overstock and returns. And you pay what this stuff probably should have cost in the first place.

And if you don’t have Nordstrom Rack in your area, you may have something regional to your area that you don’t know about. Find a well dressed dude and pretend you’re new in town. Try this: “Good sir, could you direct me to the place where people with style shop if perchance they do not have unlimited funds?”

If that fails, you certainly have Marshalls, Ross, T. J. Maxx, and the like. Are those places as pleasant as Nordstrom? No. Is it pleasant to save much bank when you shop?


Three principles Apply:

1. Be patient: you may not find what you were looking for. Go home and come back in a month.

2. Be flexible: didn’t find what you wanted? Maybe you can find something similar to fill the niche.

3. Be lucky: when you nail it, you nail it.

Jeremy was flexible and lucky, and he walked away with some choice cuts.

Timberland Boot Company. (Trust me, the “Boot Company” distinction is worthy of a closer look and a bit more money.)

Kick off with Kicks: 

A great outfit starts and ends with shoes. If you’re going to do one thing to lift your look, that’s where to do it. Jeremy and I dug through a mountain of discounted shoes, and that’s when we struck gold.

Styley meets Comfy: Timberland, which makes meh-footwear, for the most part, has a side label called Timberland Boot Company. TBC’s are very comfy, but also look like a heritage shoe. They’re well made, feature repairable soles, and have the perfect blend of old-world class and “in your face” pop. The style Jeremy found featured the classic cap toe and came in a “wear-it-with-everything” brown – but also, it has intentionally asymmetrical detailing. Just the perfect dash of “rough around the edge.”

Q: What’s more bad-ass than low-top Chucks? A: leather low-top Chucks. The grey, low-top chucks with leather laces will complete Jeremy’s already perfected jeans n’  t-shirt signature look, with enough flair to satisfy his interest in adding a bit of risk.

Timberland Boot Company Wodehouse shoes retail for $275.00 We got them for $100.00

Leather Chucks retail for $80.00. We bagged them for $50.00

As it turns out, the Styliest Color Is…


The color that goes with everything… and that highlights whatever else you’re rocking.

“What, the secret is wear a white shirt?”

Yes, but it must fit perfectly. And the weave must be a rich broad-cloth or oxford. No billowing sleeves or tenting back.

Gant shirts retail for $125.00. We got it for $60.00

The tiger can’t change its stripes… but striped on a tie can change your style.

After stepping up your shoes and putting on a great fitting shirt, the next Style-Up step is a non-silk, non-clerk, non-“I’m running for mayor” tie. My recommendations are:

1. Denim

2. Wool

3. Knit

A striped, knit tie, paired with jeans and a casual, unstructured blazer, says: “Let’s seal the deal on this account and head to Soda Popinskis to celebrate with a round of picklebacks. Although we’re probably a bit old for that. Let’s make it I.P.As.“

Chambray: Good enough for Jake Gyllenhaal. Good enough for you.

Denim Darko 

When I first showed Jeremy a chambray shirt, he wasn’t impressed. Indeed, you might not pick a chambray shirt off the rack. The color is pleasant but…familiar. Almost denim. And, well, it’s blue. What are you going to wear a blue, demin-like shirt with?


Chambray is like tofu. It goes with everything, and it takes on the flavor of whatever you serve it with. Jeremy’s new chambray shirt lets the navy in his tie pop and plays off the cuffs of his jeans.

Speaking of tofu, and since we’re on a budget, here’s a recipe for the most unbelievable, budget-friendly tofu on earth. Whoever you’re trying to impress with the chambray shirt will jump into bed with you after tasting this.

Sweat It Out

Now, add the sweater. What we see here is the magic of fly footwear, a classic shirt, a casual tie, and a teeny bit of rock-star in this John Varvatos sweater (retails for about $175.00 We found it for just over $100). The sweater itself walks the line between bohemian grunge (with it’s loose knit and straw-color) Oxford professor (elbow patches) and fasionisto (slim fit).

The effect of the gestalt is easy on the eyes — blending hints of lumberjack with Vampire Weekend Prepster – and Jeremy’s boyish good looks (somethings are not for sale at any price).

The most expensive pair of jeans are cheap

One thing Jeremy knew from the get-go was that he wanted some dope new jeans. As it turns out, my recommendation didn’t point to any multi-hundred dollar pair of gourmet hoo-hah.

It’s Levi’s.

The magic of jeans is not in the label. It’s not in the stitching. It is most certainly not in distressing or bedazzling.

It’s in pairing a perfect fit with the darkest, richest indigo you can find.

These jeans could have been $250.00 if they were made by ExpensiveDouchery. By Levi’s, they’re fifty bucks.

This style-up included:

2 sweaters

4 shirts

1 pair of jeans

and 1 tie.

Shopping the Style-Up Budget way saved Jeremy about $500, and that looks good on anyone.

Ready 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. Drop me a line at stylefordorks at gmail dot com.

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. Drop me a line at stylefordorks at gmail dot com.

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