Bonobos Friday Grey Weekend Warrior Dress Pants (affiliate link): These are slim without being super skinny so they will look sharp without being out of place. The grey will be better than black for your contrast and work environment. $98
Brooks Brothers Slim Fit Oxford Cloth Button Down Sport Shirts (aff link): You’ll want one in white, one in aqua, and one in blue. These are simple but awesome shirts that can be dressed up or down as you need them to be. $225 for all three
The Rail Long Sleeve Henleys (aff link): These are a bit dressier and more unique than a T-shirt but are still very blue-collar, casual shirts. $50 for both
The Rail White V-Neck T’s (aff link): These are the Hane’s upgrade you were asking for. $30 for two
Brixtong Hooligan Driving Cap (aff link): A driving cap is the best option for a “dressed up” hat. Fedora’s are still a bit too old and affected and other hats end up looking too casual. The grey is a good neutral color that will play off of the coat. $35
Frank & Oak Richmond Pique Navy Blazer: The fabric, single vent, and patch pockets will all help make this a great casual blazer you can throw on anything without worrying about it being too dressed up. It’s also designed to feel more like you’re wearing a sweatshirt than a suit jacket. $125
Ray Ban Classic Aviators (aff link): You’re going to want these in the silver instead of gold as it’s a cooler color. These have the perfect tear-drop shape for your face. $155
H&M Double Breasted Grey Peacoat. Similar to some of the options we were looking at last year but it shouldn’t require any extra tailoring. The grey will be better on you than the black and be less dreary in the winter months. $100
Columbia Cubist 2.0 Royal Blue Jacket: $135
Florsheim Gaffney Boot (aff link): These will still be seasonably appropriate given their lug soles, but are a bit dressier and therefore more stylish than a pair of work boots. Wear them casually, High/Low, or formally as you choose. $140
Clark’s Original Desert Boots (aff link): For the sake of avoiding repetition, I suggest you get these in any color other than the black or brown. They tan will be the most versatile with the burgundy being the most unique. $120
Remo Tuliani Andretti Brown Leather Belt (aff link): Dark brown to go with the boots. Dressy but not dainty. $60
Nordstrom Wool Scarves (aff link): You have a lot of grey for your big ticket items (which you should because it’s neutral) so you’ll want to add some color for accessories. A red scarf and a blue one will both give some good pop on long winter days without looking young or inappropriate. $50 each
Polo Brown Quilted Leather Gloves (aff link): Dressy but tough. The brown will work with your boots and belt. $60
Bonobos Travel Straight Leg Jeans (aff link): Cheaper than the APC’s but still quality enough to last a while. $98
Frank & Oak Camrose Chambray Shirt: Chambray looks like denim but feels much softer. It’s a great, year-round material that gives you a bit more of a rugged look than the OCBD’s we did last time around. $45
Frank & Oak Banford Navy Gingham Shirt: I have this shirt and love it. It’s soft and comfortable while still wearing well. $45
Frank & Oak Lewis Thermal Henley: Similar to the other henley above but the color is a bit darker and the material is thicker, making it more ideal for Fall and winter. $32
Brixton Hooligan Driving Cap (aff link): You already have one great looking but safe hat, so on your second you can get a bit more daring. The pattern is still traditional so it won’t look goofy, but it’s a ay to advertise you’re feeling a bit more casual and approachable. $36
Brooks Brothers Navy Cotton Bomber: The Boucle jacket is no longer available on their site. This looks like a close approximation and should fit your needs just as well. $150
Frank & Oak OCBD’s: Should be just as good as the BB you’ve owned before but cheaper and without the negative connotation we now have with Brooks Brothers. $45 each or $135 for all three.
Natural Blue Linen Sport Shirt (aff link): Linen is going to maximize breathability, making it the ideal fabric for hot, humid environments. Unfortunately they only have white as a solid and a couple of shades in gingham. I’d get two or three in white and one in the lighter blue and use these as my default business-casual shirts while on your trip $40 each.
Casual Button Ups
Frank & Oak Short-Sleeved, Summer-Weight Shirts: The bottom two are geared more towards versatility while the pattern of the top is a bit more consistent with the relaxed attitude of a vacation. All three are wearable all summer though. $55 for the print, $45 for the solids. $145 for all three.
Frank & Oak Newport Chinos: Navy and grey will be great for your coloring and also versatile. These will be wearable year round as well – provided you don’t go too short in the inseam. $55 each or $110 for both.
Nordstrom Reversible Belt (aft link): Similar to the other belt in that it’s dressy without being dainty, this will also cover your bases by being a lighter brown than the other belt on one side, and black on the other. $50
Tommy Bahama Straw Panama (aff link): I’ll be up front and admit that I’m on the fence about this purchase. In fact, this is the first (and probably only) time I’ve ever recommended a Tommy Bahama product, but the needs and shipping circumstances make this a bit more interesting. Here are my thoughts. A hat is going to be useful in your environment for all of the reasons men traditionally wore straw hats before the advent of A/C. It will cool you down, keep the sun out of your eyes, protect your head from bird droppings and other fun projectiles when you’re outside, and keep you covered a bit during the rain. There are a few things that prevent this hat from looking like some neck beard/reddit-atheist fedora. First, the wide brim makes it a true fedora, as opposed to the small-brimmed trilby. That’s the biggest blunder 99% of men make when buying a classic hat. Second, it’s straw instead of wool. Third, it looks like there’s no branding, ornamentation, or wild coloring. $68
Ray Ban Tortoise Clubmasters (aft link): After the aviators, these are the next step in a timeless, stylish pair of shades. They’re a bit more dandy, so they’re more appropriate for Refined and Rakish situations than super Rugged stuff. $160
Naked & Famous Indigo Jeans (aff link): A little different shade than the Bonobos from the last round, but still within a color range that makes them very versatile. $145
Venroy Sydney Board Shorts (aff link): Swim trunks are tough. Too short and you’ll come across as too effeminate, too long and you look like a teenager. These fall to just the right length and are slim without being aggressively skinny. The color makes them versatile as well. $90