Non-dorky Snow Boots — and Other Questions

In our advice column, “Ask the Strategist,” we answer your most burning shopping questions by surveying friends, calling up experts, and drawing on our own personal experience. Today, we’re answering reader questions about actually stylish snow boots, the best headphones for running, and where to find a comedians’ on-stage tees. If you want a chance to get expert advice from our team, send us an email at strategist@nymag.com with the subject “Ask the Strategist.” We’re here to help – and you may see your question answered in a future newsletter.

I am searching for a pair of black winter boots or shoes that don’t look the part, by which I mean: no sheepskin or other thick lining (my feet are always hot), no puffy outer insulation, and not hiking boots or duck style. What I would love is an ankle to mid-calf, low-profile, office-and-date-appropriate boot that is comfortable, water-resistant, and, most importantly, still has super-solid traction for snow, slush, and rain. So a regular fashion boot in sheep’s clothing (or not, as it were). 

Comedian Daniel Sloss wears these T-shirts onstage that have a red or black tag — sort of a mini-stripe — on the sleeve. What are they? I must know!

After my husband asked me how it felt to be the “last person wearing skinny jeans in NYC,” I am searching for a new go-to brand and cut to upgrade my denim wardrobe. I want something I can buy in every wash (white, black, blue, grey), can be dressed up or down, worn with flats and boots and heels, and not look wildly out of date by next season. With the exception of that last criteria, my faithful Rag and Bone skinnies had carried me through for many years, and I don’t want to have to do this again for a while.

What are the best headphones to work out with? I’m partial to the around-ears for the gym but then you can’t wear them with sunglasses when running.

How do I put together a plus-size travel wardrobe? Going to Paris for ten days in December and I need to travel light. I’m not great at getting it all into a single suitcase, and I’d like some suggestions for chic and practical items. The struggle is real.