Fall 2018: Summer to Fall Transition


  • Climate: 60-80 degrees (F)

  • Dress Code: Casual

  • Color Scheme: Brown

  • Full Outfit Price Range: $292-$683 (excluding accessories)

The Top

Timberland Indian River Slim Fit Denim Shirt:  An easy-to-wear top layer from Timberland that goes with almost anything. Put on a white v-neck underneath and you have a classic look that never gets old. $58*

Flint and Tinder Moleskin Shirt Jacket: Something with a little more body, this moleskin shirt jacket is great for when the weather is uncertain, and to throw on top of what ever you’re wearing when the cold mornings start to come through. $188*

Everlane Cashmere Crew Neck Sweater: Cashmere is perfect for the transitional weather, it’s light, warm, and breathes, meaning it will keep you comfortable without massively overheating. This cashmere sweater from Everlane is also one of the least expensive one’s you’ll find that is of good quality. However, it is dry clean only. $100*

The Bottom

AG Trellis SUD Modern Slim Fit Pants: These olive jeans will play great for the Fall transition. Made with 3% elastane they give you the right amount of stretch to let it be a little tight but not uncomfortable.  $178*

Club Monaco Super Slim Corduroy Pants: These cords are the slimmer, less bulky, more formal version of the ones you had when you were a kid and in college. They stretch a bit, and keep your trunks warm when the temps dip, while still letting your legs breathe when the sun comes out. $99*

Reiss Nillson Slim Fit Chinos: A more upscale option, these Reiss Nillson chinos are great for work and for play. The creased fronts give them an elevated look while the cotton and elastane composition keep them casual. $195*

The Feet

Cole Haan Wagner Grand Waterproof Chelsea Boots: Fall is the perfect time to rock some Chelsea boots. They have a more refined look, protect your feet, and have a decently-sized opening at the top to keep your feet and ankles cool when you’re walking for longer than 20 minutes. These are a great color that goes with your brown and black stuff. $300*

Johnston & Murphy Fullerton Chukka: These rougher-looking leather chukkas from Johnston & Murphy are the rugged cousin to their Warner Chukka. They offer a more outdoorsy, not-so-polished feel perfect for beer gardens and your eventual trip to an orchard or Autumn festival. $168*

Converse x COMME DES GARÇONS Play High-top Chuck Talyor: The most casual option, these COMME DES GARÇONS play chucks are perfect for adding a little splash of color in an unexpected place. These play great for casual bar hopping or when you know it’s going to be a dry day. $135*


Banana Republic Windowpane Cotton-Wool Scarf: Adding a scarf to an outfit in the morning, or once the sun goes down, is the perfect route if you’re worried about the cooler temps but don’t want to carry a jacket. This cotton-wool blend scarf will breathe plenty, and not be too warm for the transitional temperatures of September and October. $60*

Fossil Minimalist Leather Strap Watch: Add something simple to your outfit that makes an impact like this minimalist watch from Fossil. This is a no-frills, yet bold time-piece that will go with pretty much any outfit that includes brown shoes and belt. $115*

United By Blue Lonely Whale 5- Panel Hat: Sometimes a hat is just necessary. Those days you don’t want to deal with your hair, the weekends where rain seems like the only constant, etc. This 5-panel is a trendy, more rugged-style option that will match the more casual feel of the denim and corduroy picks in this outfitter.  $28