What I Packed: Weekend Trip With The Boys6 min read

I don’t like packing, whether for a move, a trip, whatever—I absolutely hate it. So much so that I often find myself packing in the early hours of the morning with an 8am flight the next day. Not exactly ideal, but I’ve been working on it.

What I Packed: Weekend Trip With The Boys | GENTLEMAN WITHIN

If you’ve seen the ongoing gift card giveaway (October 17-27), then you know I visited Denver, Colorado with a group of friends last week. In this post, I’ll show you what I packed.

I flew out on Friday morning and returned home on Monday evening, so it was technically a 4 day trip.

What I Packed: A Weekend Trip With The Boys

With airlines increasingly adding carry-on fees for their basic economy fares (looking at you United, Frontier, and Spirit), it’s becoming more difficult to fly, especially if you don’t have much travel experience to begin with. This makes for cheaper fares with a ton of restrictions such as no flight changes, no priority boarding and of course no full-sized carry on bags permitted.

If you accidentally forget or just didn’t realize this then you’ll be stuck checking your carry-on. The last thing you want is to be forced to check your bag at the gate for an extra $25-50 fee on top of the check bag fee.

My biggest problem has always been overpacking. Whether I’m going for a drive up to the Poconos, a short domestic flight or a trip abroad, I’m always wasting precious cargo space. The key is to only pack what is absolutely essential. Never waste room by packing something you will make no use of.

I tried heeding my own advice and here is what I packed in my overstuffed personal item.


My Travel Outfit
Airport bathroom selfie FTW!
  • 3 Jackets
    • Field jacket
    • Zip fleece jacket
    • Lightweight blazer
  • 6 Shirts
    • 3 t-shirts
    • 2 flannel button up shirts
    • Dotted button down shirt
  • 2 Pants
    • Dark wash jeans
    • Navy chinos
  • 2 Shoes
    • Leather boots
    • Suede double monk strap shoes
  • 2 Mid-Layers
    • Quilted light vest
    • Light down vest
  • 15 Accessories
    • 4 pairs of underwear
    • 3 pairs of socks
    • 2 casual watches
    • 2 belts
    • Pair of sunglasses
    • Wallet
    • Business card holder
    • Notepad
  • 6 Electronics
    • Laptop
    • Smart phone
    • Drone
    • GoPro
    • Phone charger
    • Power bank charger
  • 1 Dopp Kit
    • Toiletries
    • Facial/hair care
    • Other grooming essentials

Day 1: Travel Getup

SHOP THIS LOOK—Field Jacket: Peter Manning NYC | Flannel Shirt: Tailor Store (similar on a budget) | T-Shirt: Sharp Casualwear | Jeans: Banana Republic (similar on a budget) | Vest: J.Crew Factory | Boots: Thursday Boots Co. (similar) | Watch: Timex | Watch Strap: Cheapest Nato Straps | Socks: People Socks

It was cool in Philly upon my departure and about the same temperature in Denver. I figured the weather would cool down, especially at night so I went with layers on layers here. I always wear my heaviest items on the plane to save space in my bag.

The base layers comprise of a t-shirt and flannel button up. Layered over the shirts are a light quilted vest (J.Crew Factory Walker Vest) and trusty field jacket in olive. I love it as a travel jacket because it’s stylish, but also has many pockets to hold important documents or anything other loose items. Down low I went with my favorite dark wash jeans, and pair of beater boots that I don’t mind scuffing up at a bar or on a hike.


If you don’t mind the hassle at security, wear your heaviest items on the plane. Alternatively, if you’re a frequent flyer, it makes sense to get TSA Precheck which will essentially allow you to breeze through security without removing your shoes, laptop, belt, liquids and light jacket. It’s only $85 and lasts for 5 years.

Day 2: Hiking At Red Rocks

SHOP THIS LOOK—Fleece Jacket: Uniqlo (similar) | Jeans: Banana Republic (similar on a budget) | Vest: Uniqlo | Boots: Thursday Boots Co. (similar) | Watch: Casio | Socks: People Socks

On the second day of our trip, we decided to hit up Red Rocks, a nice hiking area 10 miles west of Denver. It’s also home to the famed amphitheater which is one of the best outdoor concert venues in the world.

I went simple here with the my beater boots, same dark wash denim from day 1, an ultra light down vest and light performance fleece. I love the vest, fleece combo for an activity like hiking because if I start to heat up I can simply remove the jacket. The vest provides enough insulation to keep my upper body warm while staying stylish.

Day 2: Night Out In the City

SHOP THIS LOOK—Blazer: Uniqlo | Shirt: Asos (alternative) | Pants: Uniqlo | Shoes: Frye (similar) | Belt: Anson Belt | Pocket Square: Nordstrom (similar on a budget 1) | Socks: Sprezza

Later that night we all went out for a night on the town in Denver. We hit up several bars and ended the night at the club. I kept things simple in neutral colors for my going out getup. Yes, I wore suede shoes, but they were cheap, so they’re kind of my beater monk straps that I don’t mind dirtying up.

You may notice the outfits are all pretty neutral—grays, blues, tans and olives. There’s a reason why I gravitate towards these colors because they’re easy to mix and match, thus allowing me to pack less, but still be able to create different looks.

As for wearing the same pants twice, I don’t mind that while I’m traveling, plus no one’s going to notice anyway.

Bag, Toiletries & GoPro

Bag With Toiletries And GoPro | GENTLEMAN WITHIN
SHOP THIS LOOK—Bag: Swiss Gear (alternatives) | Sunglasses: Warby Parker | GoPro: Hero 5 Session | GoPro Tripod: KobraTech | Toothpaste: Pronamel | Shave Razor: Harry’s | Shave Cream: Proraso | Chapstick: Burt’s Bees  Hairspray: ECRU | Shampoo: Tea Tree | Multi-Wash: Niche | Face Wash: Billy Jealousy | Lotion: A.J. Murray | Face Wipes: Ursa Major | Business Card Holder: Generic | Wallet: Anson Calder

Pretty self explanatory. We were staying at an Airbnb so I wasn’t entirely sure if there would be amenities, plus I like to use my own. I brought the essentials—toothpaste, lotion, shaving cream, face wipes, hair spray, chapstick, cologne samples, as well as face, hair and body wash. I made sure everything was under the TSA 3.4 oz. for liquids.

Extras & Drone

SHOP THIS LOOK—Flannel Shirt: Tailor Store (similar on a budget) | Hat: J.Crew (similar) | Gray T-Shirt: Uniqlo | Blue T-Shirt: Uniqlo | Drone: DJI Mavic Pro

To top things off, I brought some extra t-shirts, a flannel shirt, my ball cap and drone. It’s always good to have spare shirts just in case. And my drone which I haven’t flown too much since I’ve gotten it didn’t get much use. I was having technical difficulties while we were at Red Rock and then couldn’t fly when I was staying at my Airbnb by the airport the final day of the trip because it was in a “no fly” zone.

Though I got some footage, it was marred by my failure to remove the gimbal clamp that holds the camera in place. I ended up losing it. It just wasn’t a good trip for my drone. But I’ll see about throwing in some footage that I do have into the video above.


All in all, it was a fun trip with some friends that I’ve known for quite a while now. Denver is a beautiful city and I’ll be sure to return again. Next time to hit the Rockies for snowboarding.

Alright, I hope you enjoyed this little post on What I Packed for a trip with the boys. Perhaps I’ll make a series out of this as I learn to hone my travel/packing skills.

One last thing—on the topic of travel, if you want tips and tricks for traveling abroad, I’ve got you covered.

Onto you. How do you pack for a weekend trip?


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  1. Khoi | Gentleman Within says

    Hi Linda,

    Thanks so much for reading! That’s a great idea. I’ll have to put something together for the holidays. Cheers!

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