Five Rules for Nailing End-of-Summer Style

Let’s be clear — as much as we love being hyperbolic, summer is not actually over. The season officially runs through September 22, and, given the general volatility of atmospheric conditions in an age of climate change, we may experience balmy weather long past even that benchmark. That being said, the dog days offer an opportune time to really think about your wardrobe, as end of summer style can be both tricky and essential for a smooth transition into fall staples.

To that end, we’ve decided to really tackle the sartorial mindf*ck that is the 90-degree days, 55-degree nights, 80% humidity, torrential downpours and the like of August and September. We’ve considered it all, and come up with five specific rules — suggestions, really — to help you get the most out of summer’s end. From investment-worthy layers to easy, breezy cords, find a nifty guide to end of summer style below.

The End-of-Summer Style Rules

Be Flexible With Fabrics

With unpredictable weather and drastic vibe swings, don’t fall into the traditional seasonal binary trade. Leave the linen out a bit longer than you might think appropriate — or, better yet, invest in some that make sense for early fall, too, like a blended layer for chilly nights — and pull out your breeziest corduroy now, not October.

Universal Works Linen Cotton Field Jacket

Todd Snyder Relaxed Fit 5-Pocket Bedford Corduroy Pants

J.Crew’s Fall Lookbook Just Dropped. Here’s What We’re Already Shopping.

Including work books, shetland sweaters and a ton of corduroy

2: Don’t Sleep on Sweatshirts and Shorts

There are few sartorial joys more visceral than wearing your favorite vintage sweatshirt with a pair of shorts, and few combos that look as good, either. Don’t feel bound to summer’s arbitrary inseam rules, either — a long style is perfectly acceptable as the dog days roll in.

Trumbull Vintage Wash Crewneck Sweatshirt

Reigning Champ 6″ Midweight Terry Sweatshort

3: Find Your Footing

Your dogs might still be whining for fisherman sandals and recovery slides, but footwear is the first facet of your fall wardrobe to change, and thinking about your shoe story is critical. A ton of new launches have already hit the market — we predict that retro, slightly slimmer sneakers from brands like New Balance and Saucony are going to be huge, and we don’t foresee the boat shoe losing steam any time soon.

Noah x Paraboot Winter Boat Shoe

Saucony ProGrid Omni 9 Sneakers

J.Crew : $150 Saucony : $150

4: Test Out Tees

Are you a 100% pima guy, or do you like a touch of elastane in there? Do you want something lightweight and breezy, or an ultra-heavy boxy boy? These are the questions to answer before you start really tucking your tees into wool trousers and oversized cords — take the time to figure out your preferred style now, and reap the benefits all fall long.

Buck Mason Pima Classic Tee

Sunspel Riviera Supima T-Shirt

The Best Heavyweight T-Shirts, From Weighty to Downright Hulking

Add a bit of heft and durability to your T-shirts

5: Invest In a Quality Jacket

As insane as it may feel to purchase an ultra-insulated Arc’teryx joint in August, summer is objectively the best time to shop for a proper winter jacket: there are sensible deals galore on virtually every type of layer conceivable, along with a ton of just-dropped fall stock that won’t be available come first snow. Do yourself a favor and invest in your future.