I'm in my late 30s and have struggled the last couple years with dressing my age, especially in casual settings. I don't want to dress like a college student and I don't want to dress like a boomer. I want to get some versatile pieces that will last me a long time but I just don't know what shops to go to. Any suggestions?

Have the day off tomorrow and really need to expand the wardrobe. Any and all styles are welcome and happy to travel wherever!

As a woman, I have lots of options for shopping at neighborhood boutiques. When traveling, my husband and I will explore trendy areas, seek out vintage boutiques, and get a souvenir outfit to remember our trip, and support small businesses. Oftentimes though, the menswear sections are very small, have poor selection, or are entirely nonexistent. Do you have a neighborhood clothing boutique to recommend that has a great selection of stylish menswear? We would love to shop vintage, or contemporary, see accessories, and use fitting rooms. Not particular about the neighborhoods, though I’d prefer to avoid downtown. Less so, clean-cut “business/professional” and more so “Subtle Goth” or “Dapper Dan Man” if that helps. Haha. Thanks in advance!