Winter has a way of turning everyone into the same guy: wearing a gray hoodie and worn-out joggers on repeat until March. We totally get it. It’s cold, it’s dark at 4:47pm, and motivation is hanging on by a thread.
When winter drags on, I stick to outfits that are warm, simple, and actually fit. These five looks are my go-to rotation for getting out of the midwinter rut.
Cozy WFH Fit
On work-from-home days, I treat layering like a utility bill strategy. Jogger sweatpants, a bamboo tee, and a fleece zip-up hoodie keep me warm enough to justify keeping the thermostat low. Add thick socks or slippers, a full coffee mug, and suddenly winter feels manageable.
Midwinter Date Night Fit
Winter date nights are a balance. You want to look put together without freezing the second you step outside. This is my go-to: chinos, a premium tee, and a bomber jacket keep things clean and easy. Finish it off with leather shoes and a watch. Valentine’s Day always sneaks up this time of year, so this easy layered look is a safe move to keep in your closet.
The Tall Mountain Man
I don’t live in the mountains, but this outfit makes me feel like I could survive there. A long-sleeve henley layered under a flannel adds warmth without bulk, paired with medium wash jeans, boots, and a beanie. It’s one of those winter looks that just works, especially when everything actually fits the way it should.
The Car Scraping Uniform
If you live in the Midwest, you need an outfit specifically for scraping ice off your car. This is mine. Everyday joggers and a midweight hoodie, layered with a flannel overshirt, scarf, gloves, and a beanie. Grab the scraper, handle business, and you’re already dressed for the rest of your day.
Seasonal Depression Armor
Midwinter can get heavy, and dressing like the weather forecast does not help. I try to bring some color into the rotation when I can. Navy athletic shorts, a copper cotton tee, and a Goldie crew neck sweatshirt keep things relaxed without feeling dull. Blue tennis shoes and an evergreen ball cap finish it off. Adding color to your outfit is a small thing, but it truly helps beat the winter blues.
Winter is long, but being tall doesn’t mean you have to suffer through it in clothes that don’t fit or feel good. A few solid outfits go a long way!
