Seven Simple Steps to Bump Up Your Style-Game

This post follows my recent feature in Lifehacker’s “Ask an Expert” series. It serves as a deeper dive into some of the great questions that readers submitted.


An eye for style involves a zillion tiny calculations, many of which are subconscious. You have a “feeling” about what will work, and what won’t. But good news! Like every other skill set, when you’re new to it, you’re in a great place because the learning curve is steep! Even a small effort can net you big results.

You know that quote: the journey of a thousand steps? Yeah, you know the one.

Well, the journey of bumping up your style-game only takes about ten steps. And if you take one step a day, well, do the math.

bowling

“Thanks, Uncle Russ, for your vintage bowling shirt. Now, it’s going to live with someone who needs it more than my closet does.”

Step 1: Go through your closet and get rid of everything that is too big, too small, has a stain, or that you haven’t worn in 1 year.

Purging your closet is god for your psyche/soul/sub-conscious/feng-shui and whatever else. If you’re still holding on to Uncle Russ’s vintage bowling shirt, a lucky hoodie from the college days, or a pile of concert t-shirts with fond memories – and you never wear them but can’t bear to part with them – do what I do: put them in clothing limbo: a large cardboard box. In another year, if the absence of the garments does not have a deleterious effect on your life, donate the whole box to the Salvation Army.

Warning: do not look in the box, once it’s sealed. Maybe you’ve heard of Pandora?

2. Ask around for a hair stylist recommendation

Be prepared for sticker shock if you’re used to 10 dollar cuts. Trust me, it’s worth it. When you head out to pop some tags, you’ll know better what you like – and what you don’t – if your hair is on point.

If no one you know can hook you up with a proper rec, then go to Yelp, and trust that you get what you pay for. Aim for 50 bucks.

3. If you don’t own a pair of dark blue indigo jeans, get one.

Friends, I cannot overstate the power of dark indigo. Denim magic is only partially about fit. It is equally about color. And what white does for a masterpiece’s canvas, dark indigo does for your whole outfit. It looks awesome with anything, on anyone. And the good news is that decent, dark denim costs only 50 bucks.

Swap out that baggy, acid-wash, carpenter pair from 1997 and prepare for magic.

No other shoe is as versatile as Clarks Desert Boots.

No other shoe is as versatile as Clarks Desert Boots, which even suit a suit. So to speak.

4. Get a pair of Clark’s desert boots. Brown.

Generally, this blog is about teaching concepts and principles, and not pushing any particular brand.

But some brands set the style — and some styles, like dark denim, are so perfect, so flawless, they never fade.

Clark’s Original desert boot (which have a soft, whitish, rubbery sole, so cool but not essential – you can get away with Bushacre II) go with shorts. And jeans. And dress pants. Man, I wear them with suit.

Get your size by visiting a department store near you, then bag them on eBay for $65-75.5.

5. Get a white OXFORD or CHAMBRAY shirt in the smallest size you can fit into.

Most of the usual suspects carry Oxford Cloth Button Downs for $40-75. Just to be clear, this is not a white dress shirt. Oxford cloth is nubbier, more causal – sort of a hybrid work/office shirt. It looks great on everyone (including women). And it looks great with everything.

Likewise, Chambray (click here for a deeper dive) is not denim, though it looks a little like it. Pick one up on eBay, or at J.Crew, Banana Republic, Gap, or a local resale shop. 

knittie6. Get a knit tie from TieBar.com

You don’t wear ties? You do now. 

7. Finally, get either a blue or grey blazer… Or a thick, cuddly cardigan.

You don’t need to drop bank. A decent cardigan or blazer might run you fifty bucks. Be sure it is snug, and here’s a rule of thumb: even if it’s too tight to button, it’s a great layer piece. Do not, under any circumstances, buy a big, boxy, hanging blazer – no matter the brand.


You have completed your seven-step journey.

Prepare for complements.

before after

All seven steps, done as one. Sepia tone optional.

Want to see all seven steps, completed in an hour? Read the story here.

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