"I've spent a lot of time lately thinking about buying fewer but better things. Investing in quality over quantity is not a novel concept, of course, but it's been top of mind recently as I've been frustrated by some inconsistencies from brands I've turned to for a long time. So this year I'm all about upgrading. Below, five items I think would fit nicely in my closet and yours, for many years to come."
"Madewell's 1991 straight-fit jeans have been my primary denim of choice for the past few years. But recently, I've been frustrated by their lack of consistency. I have three pairs, all in the same size, currently in rotation, and the fit is noticeably different in each. So I've spent the first few weeks of 2026 in a rabbit hole of denim research, and I'm thinking the time is right for me, for all of us, to upgrade to something like these highly regarded Orslow 105s."
All products are independently selected and vetted by InsideHook editors; purchases may earn an affiliate commission. A not-insignificant purchase is recommended as a weekend reward. The focus is on buying fewer, higher-quality items and investing in quality over quantity due to frustration with inconsistent brand products. Suggestions include upgrading denim to highly regarded Orslow 105s after noticing inconsistent fits from Madewell's 1991 straight-fit jeans across identical sizes. A $700 pair of Alden chukka boots is presented as costly but unrivaled for balancing casual and dressed-up styles and made in the United States. A lightweight, extremely warm, and durable item is praised for flawless performance, and a winter coat is described as both timeless and a statement piece.
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