Steppin’ outside the comfort zone

This whole wedding deal is totally challenging my inner frugal self. I’m just not a huge fan of money leaving my accounts. I love putting in it, and hate taking it out. It’s pretty stupid when you think about it actually. It would be like if I bought a really nice cut of meat, but didn’t want to cook/eat it because I like the way it looks in my refrigerator. Money is meant to eventually exit your investment/savings accounts, much like food is meant to be eaten. Whether it be through bills, luxuries, donations, or death, every dollar I’ve saved will eventually find itself a new owner.

The wedding is less than four weeks away now and the expensive part (for me) is quickly approaching. I’m about to buy all of my groomsmen gifts (which I’m convinced are the best groomsmen gifts ever), have to buy the parents gifts for all of their love, support, and contributions, and I have to buy some new clothes. I’m totally fine spending money on my wedding party and family as giving gifts has never been hard for me, but I hate thinking about spending money on clothes.

Most of my work shirts have gotten a decent amount of use out of them and no longer look as bright or crisp as when I first bought ’em. This means I’ll probably be heading to Express for Men or Banana Republic to pick up an outfit for the rehearsal dinner. Maybe something like this…

If one nice outfit was my only expense, I wouldn’t be freakin’ out. Unfortunately, I am in desperate need of some Aruba appropriate clothing. You know, shorts, tank tops, linen shirts, etc. I literally own zero clothes that are nice enough to be my honeymoon outfits. In fact check out this picture of my favorite pair of shorts. Can you say ghetto?….

I literally have not bought a single pair of shorts or pants in the last two years. I wear everything until it falls apart, but Girl Ninja wants me looking a little less ugly on our honeymoon and I can’t really blame her. Do you know what this means? Shopping spree. Notice there was no exclamation point at the end of the last sentence. It’s not something I am excited about, but I know it needs to happen. I can’t drop big money on a honeymoon, only to be dressed in a pair of shorts I made from army pants I bought at the thrift store (I actually did that once).

I don’t really know where to begin looking for sweet threads, but I will most likely begin my journey at Nordstrom Rack, they seem to have a little bit of everything there. I’d love to keep my total spending under $200, but with GN helping me pick out my outfits I could be looking at a much larger bill than desired. She’s kind of a clothes whore (don’t tell her I said that).

I need help from you fashionistas. How do I go from “beach bum” to “Aruba ready” on a budget? I feel like I’m suppose to look like this guy when I’m on my honeymoon….

When all my outfits are more like this guys (not really)…

Any advice on cost effective ways to clothing shop on a budget would be greatly appreciated, especially if you dudes have any insight.