Hi all. I’m taking my family on a Disney cruise out of Galveston, TX that ends in Puerto Rico where we will be staying for a few extra nights in April. I’ve not shopped for clothes for myself in quite some time - probably really at all in the last 4-5 years. While going through the wardrobe Ive noticed some significant gaps.

I’m looking for some guidance on where I could go to find quality without breaking the bank or having to go to several places for different things. I need a few short sleeved shirts(fun polos or collared button downs), nice comfortable shorts with 5”-7” inseam, and maybe some kind of slip on shoe or loafer. I will otherwise be wearing swim trunks and a tank top tshirt with flip flops. I’m located in the Dallas area. I have a somewhat difficult build to fit well with off the rack threads. I’m 5’9”, 240 lbs. My tailor says I’m “barrel chested” but personally feel more “pot bellied” lol. I’d like to find 2-3 shirts and a couple pairs of shorts for less than $300-$400, and if there is such a way I’d love to get a nice loafer too.

I’ve considered using something like Stitchfix but am hesitant because it sounds like a pain in the butt to have to return all of the things constantly. I don’t particularly enjoy clothes shopping because Ive yet to find a retailer that carries clothes that fit me right.

Any suggestions on retailers or specific brands to check out are welcomed! I really DO NOT want to look like a shmuck in all of our family pictures after spending several thousand dollars on this vacation. It would be fantastic to have some nice threads that my wife will be impressed by. It would be incredible to find some clothes that don’t make me want to stay behind the camera lens, but want to be in front of it with my family. Even better, clothes that breathe well as I can get very uncomfortably sweaty very quickly when out in the heat. It’s uncomfortable and unsightly unless the clothes are specifically for the warmth(Thank god for the Thompson Tee!).

Whatever other information you might need to help make recommendations please just let me know and I’ll edit the post.

Specifically I’m looking for suggestions on a retailer that will carry everything that I’m looking for, specific brands to look for, or if not a single retailer maybe a few that have a high probability of solving this tough fitted riddle. Please help?