105 Men's Summer Style Essentials to Carry You All Season—and Beyond

Style made easy, the LIVE A LITTLE way. Curated into 17 timeless outfits that land.

LIVE A LITTLE is a style and lifestyle journal for the adventurous man—written from the pen of a former magazine editor turned menswear copywriter.

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105 Best Men's Summer Style Essentials

The style philosophy here at LIVE A LITTLE is simple: comfortable, versatile, timeless. In other words, do not overthink.

This master guide below is a culmination of months of work and research, mostly conducted through my weekly FIELD JOURNAL. You’ll find I’ve broken down these picks into 17 different outfits, each holding their own use-case and designation. Some outfits are activity specific (like hiking and training), while others are tied to different aesthetics.

An example of my summer concert outfit. I always like having a layer for when the sun goes down, but this look can easily do without. Miller Lite recommend for a good time.

Another cool thing about these style essentials: you’ll discover watches, grooming products, gear, and reads. It’s a subtle nod to the menswear saying, “Style doesn’t make the man, but it does help enhance his story.”

My last note before you go is to remember these outfits are interchangeable. Swap in shorts for the pants. Ditch the layers, or opt for a thinner pieces. Make it flow with the current wardrobe you have now.

LIVE A LITTLE

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The Lake Weekend

• Garrett Leight Kinney J Sun ($495)

• Outerknown The Slow Down Shirt ($148)

• Flint and Tinder 265 Chino Short ($68)

• Shinola Duck Watch ($550)

• OluKai Tradewind Sneaker ($100)

• Rugged Road Ultralight Cooler 25 Cans ($250)

The Vacation Sprezzatura

• Raen Wiley Matte Rootbeer/Brown ($170)

• Portuguese Flannel Seersucker Camp Shirt ($148)

• 501® '93 Straight Fit Selvedge ‘Beautiful Disaster’ Wash ($148)

• Birkenstock Arizona Taupe Suede ($135)

• Highland Glacial Clay Pomade ($27)

• DOXA Sub 200 ($1,050)

The Siesta Key

• Vallon Howlin’ Shades ($138)

• Bass Pro Shops Quality Gear 5-Panel Cap ($15)

• Flint and Tinder Linen Long Sleeve Button Down ($128)

• Flint and Tinder Cotton Linen Drawstring Short ($88)

• Sperry x J.Crew Roughout Suede Boat Shoe ($125)

• Q Timex® Continental GMT 39mm ($189)

The Hybrid Trainer

• Huega House Tidal Nylon Hat ($40)

• SUUNTO Run Coral Orange ($249)

• TENORE Reversible Scrimmage Jersey ($88)

• Wellen Sevens Sport Short Lined 7” ($78)

• ASICS GEL-CUMULUS 27 ($140)

The Trail Junkie

• Patagonia Broadcaster Hat ($39)

• Ombraz Classic Armless Shades ($160)

• Patagonia Go-To Shirt Salt Grey ($79)

• NANGA Ripstop Field Pant ($155)

• Blundstone #2442 Chelsea Boots in Forest ($210)

• Suunto Vertical ($699)

The California Cool

• Todd Snyder Made in L.A. Jersey Polo ($128)

• Baracuta G9 Ripstop Jacket ($349)

• 7 for All Mankind Airweft Straight ($248)

• Todd Snyder x New Balance 574 Legacy ($120)

• Lucky Brand Triple Needle Stitch Leather Belt ($30)

• ’47 Brand MLB Los Angeles Dodgers Clean Up Hat ($29)

• Q Timex® 1982 Ana-Digi Reissue ($189)

The Old Money

• Moscot Lemtosh Sun ($370)

• J.Crew Waffle Knit Rugby Shirt ($53)

• J.Crew Classic Chino ($98)

• Woven Elastic Belt ($29)

• adidas BW Army ($120)

• IWC Pilot’s Watch Mark XX (See Price)

• In Our Time by Ernest Hemingway ($7)

The Rugged Explorer

• Vallon Ventures Shades ($116)

• i+w Military Shirt Jacket ($275)

• Taylor Stitch Organic Cotton Tee ($45)

• Taylor Stitch The Carmel Pant ($148)

• Seavees Acorn Trainer ($130)

• Bulova Hack Watch ($340)

The New Yorker

• 47 Brand Clean-Up Cap ($30)

• Sunski Tango ($78)

• Flint and Tinder Classic Oxford ($88)

• 3sixteen CS-100xv Vintage Wash ($310)

• Blundstone #1609 Chelsea Boots ($210)

• The Paper Menagerie and Other Stories by Ken Liu ($12)

• Oris Divers Date (See Price)

• Highland Glacial Clay Pomade ($27)

The Always Comfortable

• Garrett Leight Adonis S ($640)

• imogene + willie The “Relax” Wakefield Hoodie ($235)

• imogene + willie Rust Knit Pocket Tee ($75)

• PROOF Rover Double-Knee Work Pant ($138)

• Sabah Alto Boot ($395)

• Hamilton Field Khaki Quartz ($445)

The Concrete Explorer