It's no secret that sportswear-inspired tailoring, shoes and ensembles have dominated both the runways and streets the past seasons. That might be old news, but these are definitely of-the-moment: basketball jersey shorts, translucent windbreakers and mid-calf socks with sneakers. A relaxed silhouette bottom accompanied by socks pulled high make the look. But if you're putting off biting the bullet, try some sleek tailoring up top (a little Thom Browne never hurts) with mid-calf socks to ease yourself into the trend. Your next move? Loose-fit shorts and a pair of running trainers.