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What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. This summer has been one heat wave after another, and it feels like respite may never come. But early September can bring the occasional cooler summer’s eve. You know the kind, an early taste of fall. Temperatures drop into the 60s and a crisp, refreshing breeze rustles the leaves in the trees and refreshes your being. There’s no moment quite like it, after a long hot summer.

The Sweater: Banana Republic Merino Crewneck in Forest Green – $31.49 ($79.50). Cooler temps bring longer sleeves, and this temp-regulating merino wool crewneck sweater keeps you just warm enough without overheating. Raglan sleeve construction for more comfort and mobility, as well as accentuating your shoulders. A plus for broad-shouldered/chested fellows. Color shown here is “forest green,” which, as you can see, is between a gray/green. Heavy on the gray. Currently on sale and getting an extra 50% off cut at checkout.

The Jeans: Bonobos All Season Jean in Dark Wash – $99. Description says dark wash, but these are a true blue jean. A soft, flexible, comfortable pair of denim in a foundational color for “all-season” wear from the fitmasters at Bonobos. Not sure these will stand the test of deep winter, but they work just fine as a late-summer pair of jeans. Too spendy? Try these from Target’s Goodfellow & Co. line for $29.99.

The Shoes: Allen Edmonds Nomad Derby in Grey Suede – $149.97 ($349). Mid-grey suede is an excellent transition texture and color for late summer into early fall, and that’s at the heart of this style scenario. While it can still feel very much like summer during the day, those crisp nights offer a glance into the cooler full-day temperatures ahead. Mid-Gray bridges the gap between summer brights and rich fall tones, while the suede keeps us rooted in casual summer vibes. Even if the sweater leans more gray than green, the stark separation provided by the true blue jeans works. These derbies are from the AE lightweight “nomad” line. So don’t expect heavy or clunkiness here. Also know that these are one of their “imported” models, and not made in the USA.

The Belt: J. Crew Braided Italian Suede Belt in Auburn – $49.50. Braided belts are a casual wear staple of summer, and a great way to add more color and texture to an outfit year-round. This sueded braided belt from J.Crew nails both marks with great success.

The Watch: Orient Kamasu Diver in Stainless Steel/Green/Black – $280 ($460). When the sun comes down, you want a watch with quality lume at an affordable price. Orient is tough to beat for the price on the quality-to-price scale, and tough as nails all around. The Kamasu might be their best watch available today, and looks exceptional with a green dial.

The Socks: Bombas Black Hive Calf Socks – 4 for $46. Bombas makes really excellent socks, whatever flavor you choose. And they, like the belt, are a great place to add a little flourish.

For Those 21 and over: The Glencairn Whiskey Glass – $8 and Old Forester 1920 – $60. This is the glass to own for properly drinking bourbon, and Old Forester 1920 is a staple on my bar cart for good reason – it’s easy to find, properly priced, and has a rich and unique flavor.

About the Author: Jason P. spends his days working in the creative marketing department of a big telecom company. He also does a bit of real estate investing on the side. He believes in curating a timeless, classic wardrobe with subtle modern touches for today. He and his wife love hiking with their dog and shopping at local small businesses and antique stores when they travel. Jason is a practitioner of muay thai and traditional boxing, and his favorite drink is a hoppy New England IPA.

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