How To Fly And Be Fly While Traveling: My Style Guide

Packing for a trip is a PAIN.IN.THE.ASS. We always have the urge to bring our entire closet so we can maintain our unique sense of style, but that’s not realistic. Whether I’m going away for a three-day trip or for a couple of weeks, it’s impossible for me to not stress over what clothes I want to pack or how much I should pack. There are so many factors to consider such as, “What do I wear if it gets unbearably hot and the sun falls onto the earth? What do I wear if a tsunami decides to just show up? And what do I wear if the zombie apocalypse happens?! Do I get to look as cool as Brad Pitt in World War Z at least?”Alright, thats a bit over-exagerating but you’d be lying to yourself if you said you didn’t ever think of packing clothes for every possible weather situation. Next thing you know, you’re throwing random shit out of your closet such as your pants, shirts, socks, shoes, and underwear into large bags with less than 24 hours until your flight. Not fun.

“You want to maximize your outfits with the minimum amount of clothing possible.”


But it doesn’t have to be this hard, nor should it, I promise.

The Key To Success

You want to maximize your outfits with the minimum amount of clothing possible. When I pack, I generally pack for ten days of clothing (average length of my trips) and outfits without the need to ever do laundry.

Pick a Style….

If I’m visiting major cities, I focus my style around Street and Smart Casual. If I take the adventurous route and partake in hiking and/or other physical activities, I’ll focus on athleisure and fitness wear. For those trips to the beach, well, I pack a bathing suit. And if it’s a little bit of everything, then I pack for a little bit of everything…..and it IS possible.


….then Pick a Color

To help mix, match, and maximize your outfit possibilities, it’s best to pick a central color to focus on. This allows you minimize the amount of clothing you need and the ability to free up space in your luggage. I always choose Blue and/or Black. For a Blue example, I’ll pick a blue patterned button-down shirt, khaki colored chinos w/ a light brown belt, and a pair of dark brown leather Chukkas. For a Black example, I’ll pick a black extra-long tee, khaki colored chinos w/ a light brown belt, and a pair of white adidas sneakers.


For more on how to mix and match complimentary colors to style with, check out this amazing article here.

How Much I Pack

This is the amount of clothing I pack from most amount to least: shirts, underwear, socks, pants, shoes.

  • Shirts: I generally pack two (or 1.5) shirts per day (one for the day, one for night)
  • Underwear: 1.5 per days of travel
  • Socks: See above ^
  • Pants: This is where you will save the most space. Unless you plan to dirty your pants, sweat in them profusely or spill food all over them, then four to five different pants is all you need (or one-third the amount of shirts). Seriously, thats it.
  • Shoes: Three MAX


What I Pack: (10 Day Trip)

Street & Smart Casual

  • Shirts: 1 Classic White T-Shirt (Hanes), 3 Extra-Long Tees (Pac Sun), 3 Short-Sleeve Button Down & Chambray’s (H&M or Pac Sun), 3 Long Sleeve Button Downs (Bar III), 3 Long Sleeve/Henley Tees (Old Navy, H&M, Anywhere). (For cold weather, replace Short Sleeve shirts with Sweaters)
  • Underwear: If you really want to know…2 Compression Boxers (Under Armour)(1 Black and 1 Grey for white pants), and 12 Boxers/Briefs (Calvin Klein or Hanes)
  • Socks: 6 pairs of “crazy/fun” dress socks (Five Four Club) and 6 pairs of no-shows (Galiva Men’s No Shows)
  • Pants: 1 Khaki colored Chinos (Levi’s/Pac Sun/ H&M), 1 Blue colored Chinos (Levi’s/Pac Sun/ H&M), 1 Khaki colored Street Joggers (Levi’s), 1 Blue colored Street Joggers (Levi’s), 1 Pair of Dark Navy Jeans (Levi’s), and/or 1 pair of White/Grey slacks (Dockers). (For shorts- 1 pair of 6” Kahki color from H&M)
  • Shoes: 1 pair of leather-brown Chukkas (Clarks or Aldo’s), 1 pair of White Sneakers (Adidas or Vans), 1 pair of light brown loafers w/ or w/o monk strap (Steve Madden) or 1 pair of blue suede dress shoes (Bar III)

Disclosure: Yes, Levi’s are my go-to pants because they have every possible fit, color, style, and size option humanely available.

Athleisure and Fitness

  • Shirts: Multiple Under Armour, Nike and Champion “Heat Gear” T-Shirts which is quick-dri and moisture wicking (Available in long-sleeve)
  • Underwear: Mostly all compression boxers (see Street & Smart Casual)
  • Socks: Below the ankle black socks from Adidas or knee high black Nike’s
  • Pants/Shorts: Under Armour 5” quick-dri running shorts (super light), Foot Locker or Champ’s 6” mesh shorts, Champion jogger pants
  • Shoes: Light-weight and durable Nike Free RN sneakers

“The outfit combos are endless.”

How I Combine Them

Style 1: Classic Plain White Tee (Hanes), Dark Navy Jeans (Levi’s), Leather Brown Chukkas (Clarks)


Style 2: Extra Long Baseball Tee (Modern Amusement at Pac Sun), Khaki Street Joggers (Levi’s), White Sneakers (Adidas)


Style 3: Denim Button Down (American Rag), Khaki Chinos (Levi’s), Leather-Brown Chukkas (Clarks)/ Blue Suede Dress Shoes (Bar III)


Style 4: Blue Patterned Short-Sleeve Button Down Chambray (Pac Sun), Blue Street Joggers (Levi’s), White Sneakers (Vans)


Style 5: Light Grey Henley Long-Sleeve Tee (Oakley), Blue Khaki Chinos (Levi’s), Leather Brown Chukkas (Clarks)


Style 6: Light Blue Short-Sleeve Button Down Chambray (Modern Amusement at Pac Sun), Khaki Street Joggers (Levi’s), White Sneakers (Vans)


Style 7: Dark Blue Button Down Long-Sleeve (Bar III), Grey Pants (Dockers), Blue Suede Dress Shoes (Bar III)


As you can see, I utilized only four (optional five) different pants and only two (optional 3) different shoes to create a very simple, yet different and unique style. I could literally go on forever by mixing and matching those clothes to create at least another seven styles. The outfit combos are endless.


“Combinations are the key to traveling in style”



Additional Items & Accessories

There are a couple accessories I like to bring along with me too that I wear in order to personalize my look to accompany the combinations of my outfits. Combinations are the ket to traveling in style.

  • Jacket: If it gets cold, I always pack my Black Leather Bomber Jacket with the grey zip-on hood option by Calvin Klein ($80). It goes with EVERYTHING.
  • Belt: Light Brown leather belt by Tommy Hilfiger ($45) (to save money, look for the reversible 2 in 1 black and brown belts)
  • Watch: Brown Leather-Strap Timex with Gold Face finish ($75)
  • Bracelets and Bangles: Tom Hope Navy/Gold Anchor Bracelet ($75) and Brown Leather Bohemian Bracelet ($15)
  • Sunglasses: Ray-Ban RB2180 Tortoise ($140), Ray-Ban Clubmaster Black/Gold ($150)
  • Hat: Burberry Beanie ($150)
  • Backpack: Hershel Black Two-Zipper Backpack ($65)
  • Flying/Transportation: Nomad Hoodie ($150). See my Nomad Hoodie review here

Style Accessories

Comment below on what your traveling style is!

World Traveling, Coffee Addicted, US Army Veteran


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