By Jamie Waters

1. I used to work in the big-bank world but now have my own small advisory practice. I'm looking for clothes -- for the office and off-duty -- that bridge the gap between formal business dressing and casual golf clothes. Also, do you have any favorite sources of style inspiration for finance guys?

-- Jake Hamlin, 38, Chicago

When dressing smart-casual today, it's easy to wind up a modern corporate drone in clingy, stretchy polos and "tech" pants. So, first, some ground rules: 1) Avoid fabrics spiked with more than about 2% elastane; 2) If you're ever trying on a garment and find yourself wondering "Can I get away with something this tight?" promise me you will stop shopping and screw your head back on.

Onto the essential items. A quality polo with a slightly relaxed fit is a finance guy's best friend. Grab ones in cotton piqué or merino; a cable-knit mixes things up. Think navy, cream or shades you'd find on a tree. Alex Seo, a stylish 33-year-old with a New York investment management firm, calls the sub-$200 knit polos from Beams Plus "awesome quality and value." He also likes King & Tuckfield's more-adventurous designs. For a steal, check out Kent Wang's $75 piqué takes.

An easy tech-pants upgrade: five-pocket pants in textured cotton twill or cotton-linen. They typically retain the familiar cut of straight-leg jeans, but skew slightly dressier. And I'd step into slim-sole loafers or lug-sole derbies. Both read current and classy and, crucially, are not "hybrid" dress-shoes with sneaker soles, which are harder to defend than an impulsive crypto trade.

If you want to look like A Finance Guy, hit up brands that are reinvigorating trading-floor staples. Le Alfré's shirts -- Oxfords with white contrast collars; chambrays with stripes nearly as fat as an '80s banker's tie -- suggest Gordon Gekko's button-ups put through a "Casual Friday" filter.

Jacques's precise quarter-zip sweaters and P. Johnson's shockingly handsome navy linen vests force anyone who has mocked finance-bro staples to eat their words (I'm gorging on mine).

Alternatively, you could dress like a suave guy who just happens to work with money. Seo loves classic-but-not-corporate jackets from the Armoury, including the safari styles. Zach Garst, a trendy Houston tax consultant, 28, pairs cotton slacks with "something a little more spicy," like boxy shirts and cardigans from Auralee and Frizmworks.

For style inspo, Le Alfré founder Brandon Snower recommends @schoonerscorer, an Instagram account popular with finance guys. It features videos of a charismatic Brit -- Alex Hendy -- rating beers at pubs. He's stylish but never mentions clothes. After bingeing clips, I can tell you that I won't be slurping the ho-hum porter at one central London pub, but I do need Hendy's cream cable-knit sweater and red Ralph Lauren shirt. I like that he's not a "fashion influencer" -- outfit-dissecting accounts often come off cringe -- just a cool guy doing his thing.

One menswear account I do enjoy: @the_daily_mirror. Founder Manish Puri, who works in financial services and writes about menswear, radiates unprecious elegance with flowy trousers, suede chore coats -- and a cartoon chicken head superimposed over his own.

My best outfit ideas come from scrolling sites like Mr Porter, Drake's and Buck Mason to see how their models are dressed. A favorite corporate-cool look by P. Johnson (above) is inspiring me to do up just a few shirt buttons, buy a cowboy belt and a bro vest, and apply for an internship at JPMorgan.

2. Any cargo-shorts rules? I say they're OK due to the extreme functionality. I carry lots of useful stuff in mine, like a Gerber multi-tool and amateur radio gear.

-- Harry Bloomberg, 68, Pittsburgh

Anytime someone praises a clothing item's "extreme functionality," extreme anxiety stirs in my stomach. Like other wonderfully practical items such as caps with back flaps, the utility of cargo shorts often comes at a cost to others' eyeballs. Most cargos -- long as Capri pants, wide as a bison -- are terminally unattractive. But the best-looking ones get a pass.

Five tips to avoid channeling a style-allergic dad:

   -- Seek out shorts that boast a streamlined cut with empty pockets -- and 
      don't bulge like a packhorse when filled. 
 
   -- Ensure they end above the knee: a 9-inch inseam max. Any longer lurches 
      into Frumptown. 
 
   -- Go for navy, black or olive. Approach khaki and camo with extreme 
      caution. 
 
   -- Bypass heavy cotton for fresher linen blends or sporty performance 
      fabrics, said Michael Maccari, a super-stylish menswear designer and 
      professor who admittedly sometimes wears cargos. 
 
   -- Limit use to casual settings where you might reasonably need to haul a 
      truckload of supplies on your thighs. Radio work and plane trips qualify. 
      Dinner out does not. 

I tried a bunch of cargos to find the most palatable. I sought to mimic your haul by stuffing the pockets with items from my work bag. I replaced your radio gear with a bulky laptop charger, and swapped out your multi-tool for a pot of "Rough Rider" hairstyling clay for "a slick, matte look that lasts" (let's not dwell on it). Some shorts recommended online looked lousy IRL, though I didn't mind the belted, hiking-style takes by Uniqlo and Gramicci.

The sleekest? A cotton ripstock pair by surf brand Finisterre. Lean, subtly sporty and the color of an avocado's rind, they looked far too good to be accused of "extreme functionality."

The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.

(END) Dow Jones Newswires

June 20, 2025 14:00 ET (18:00 GMT)

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