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Jack Erwin's Hubert Long Wing Blucher retails for $195, and comes in black and chocolate brown. Jack Erwin / Samantha Lee

As part of an ongoing series, each week Insider Picks features a product or store that’s poised for big things. The subject of this week's "We're Obsessed" segment is a men's dress shoes startup called Jack Erwin .

Dress shoes pose a conundrum for many guys: On the one hand, you want your shoes to be comfortable and of high craftsmanship; on the other hand, you don't want to have to spend upwards of $500 on a pair to get those features.

Paying for quality is smart, but not everyone can (or wants to) spend more than $200 on a pair of black lace-ups or loafers. This notion resonated with Ariel Nelson and Lane Gerson, cofounders of the wildly successful men's footwear company Jack Erwin — so much so that they quit their day jobs to start this venture.

"We built Jack Erwin because we couldn't find the shoe we wanted — so really we are the best representation of our customer. We focus on what we would want from a brand and go with it," Nelson and Gerson told Business Insider.

Since launching the direct-to-consumer company back in 2013, Jack Erwin has come to offer 16 different "well-made, beautifully designed shoes at an affordable price," ranging from suede driving loafers to leather bluchers and boat shoes. In keeping with the mindset of company's namesakes (Nelson and Gerson's fathers, "two men who appreciate great shoes, but who will never pay more than $200 on a pair"), the most expensive three pairs in its collection are just $220. The other 13 are less than $200.

For today's wolves of Wall Street, that's a deal. For comparison's sake, the average Salvatore Ferragamo loafer will set you back at least $500, if not $600 or $700. Even Allen Edmonds dress shoes, which are by and large what the majority of finance guys wear (or aspire to wear) on a daily basis, run closer to $400 a pair on average.

Accessibility is a very much an issue in the men's dress shoe market; and it's one Jack Erwin is tackling — not only by offering its customers affordable prices, but by accompanying those prices with style and comfort that can rival much pricier pairs. "After the break in period, comfort is very important," Gerson explained to us. "To really look good and feel good you have to be comfortable. We have worked with our factories in Spain to find high-quality leathers that soften as they wear. We've increased the flexibility of our insole boards and leather outsoles, and we've introduced rubber sole options to further address comfort and durability," added Nelson. They just look great on top of that.

If you're in the market for new oxfords for work, or casual loafers for weekends, have a look. All signs point to Jack Erwin being a solid investment.