Saying goodbye to summer is hard, but with the right attire, feeling comfortable as the temperatures drop is easy. We asked style expertIan Michael Crumm to share his favorite pieces for transitioning from summer into fall/winter fashion. Think the best new sunglasses, flexible sweaters, and stretching out how long you’re wearing shorts.
Whether you’re gearing up for chilly outdoor workouts or searching for a way to stop city wind gusts, Canada Goose’s hoodie is ideal for unpredictable fall days. It even has a drop-down tail to help keep you dry when it starts raining.
Vertical Stripe Crew Sweater, LACOSTE ($250). 3146 M St. NW, 202-965-1893
Nautical influences seem to permeate every season’s trends—even in the fall. Pair this crew sweater with black pants for a city dinner look or Bermuda shorts and a tee for an early fall bonfire at the beach.
Pair this pullover with a collared shirt for a different take on fall’s usual shirt-and-sweater look. The side vents add a little extra ventilation to account for this season’s in-between temperatures.
Take your T-shirt game to the next level of warmth with cashmere. Naadam works with Mongolian herders to support their economy, resulting in access to rare, quality cashmere. They also buy directly from the herders, which means a very reasonable consumer price point.
This antibacterial and moisture-wicking tee is a great transitional layering piece for the gym or a casual day. Add a blazer to dress it up and stay confident that you’ll look fab—even if the unpredictable weather makes you sweat.
These wool twill trousers style well with a fitted T-shirt during the day, and look great with a light jacket on cool fall evenings. Incorporate them into your wardrobe as a refined yet comfortable staple.
1919 Datetimer Eternity Black Editiron watch, Porsche Design ($4,300). porsche-design.us
This Porsche Design timepiece mimics the aesthetics of the legendary Porsche 356. Like the sleek, classic car it's designed for, this watch will never go out of style and looks good no matter the season.
These black Louis Leeman loafers are perfect for lounging around the house on autumn’s cooler evenings. The added tassel studs and textured body make them stand out without straying too far from refined.
The elegant Flight sunglasses come in 18K gold with vintage green lenses, matte navy with dark blue lenses, and matte black with blue mirror lenses. With comfortable titanium nose pads on all variations, you can be confident that they'll transition from the beach to pumpkin lattes to chilly winter days seamlessly.
Denim usually makes a huge comeback every fall, so why not wear your jeans... on your sunglasses? These blue denim Recif sunglasses balance out the bolder material with a medium frame size and classic shape.
What better way to remember summer than with sunny yellow accessories? This contraption is pocket-sized and thin enough to slide into a non-Radio-Frequency Identification (RFID) blocking wallet to keep cards and information safe. Yellow full grain leather is paired with stainless steel fabric for a clean finish.
Style expert Ian Michael Crumm covers the latest trends in fashion, home, and design.