The Gents Fall Lifestyle Guide | Tuckernuck

The Gents Fall Lifestyle Guide

By Tuckernuck on

A Weekend in the Berkshires

Sure, summer is great and all, but we’re pretty excited for things to cool down a bit. So whether you’re planning a fall weekend away to enjoy the cooler temps or you’re just looking to update your wear-to-work, on-a-date, walking-the-dog wardrobe, we’ve got plenty of outfit ideas (just keep scrolling.)

Arrive in Style

Here’s how to avoid the sweatpants-and-t-shirt look for traveling, good for both taking the train to a weekend getaway and catching the red-eye to see a friend.


The whole point of layers is that you can add and subtract them. We shed coats and scarves for a little bike ride around Blantyre, this estate-turned-hotel.

Late Night Poker

Is it really fall without a sweater and plaid shirt? We think not. Sure, you could be chopping wood, OR you could be schooling everyone in a game of poker (at least the latter wins you a few bucks.)

Morning Hike

The Berkshires are known for their awesome hikes, so before lunch in town we take to the trails in comfy vests.

A Fancy Dinner

Whether you’re headed to a fall wedding or just a 7 course meal your better half signed you up for (see below), these outfits will make sure you’re in suitable attire.

We like to add a fun-but-appropriate fall tie to the mix. It’s an underratedly easy way to change it up.

Sunday Football & Picnic

Here we’re at a cool music venue called Tanglewood; we brought along a good spread and a football for the intermission.