On-Trend Men's Secondhand Winter Staples Under $20

This month's blog post features tips and trends from @itsizzylugo, one of Goodwill's 2026 influencer partners. Izzy is a Milwaukee-based creative and content creator known for blending streetwear, sneaker, sports culture and everyday storytelling into relatable content.

Where Streetwear, Vintage and Workwear Meet

As a creator that lives at the intersection of streetwear, vintage and workwear style, I approach winter fashion through a functional lens – think cost-efficient statement pieces that go well while layering. Finding these at Goodwill is one of the easiest ways to build a winter wardrobe that feels curated, in style and still under $20 apiece. 

I pulled together a couple of winter looks that encapsulated a few fashion directions that I have been focused in on from the fall/winter 2026 trends like oversized jackets, neutral layering pieces and bold colored accessories that elevate any cold-weather fit.  

Here’s what I found and a few tips to keep in mind.

When thrifting winter looks, focus on must-have categories that offer the largest return in warmth like these quality outerwear pieces from Eddie Bauer: 

And, these heavyweight jackets from Eddie Bauer and Realtree:

Pair with bottom options from Wrangler, Carhartt and Dickies. These pieces are quality brands in the workwear style that is on trend right now, not to mention, I thrifted these from Goodwill basically brand new:

Moral of the story, when shopping at your local thrift store like Goodwill, keep a look out for textures while combing through the racks and prioritize pieces that layer cleanly into your existing closet. With a little patience and eye for quality, you can build a winter fit that feels true to you but is also nice for your wallet.