The Broke Bachelor's Guide to Fancy Dressing on the Fly

Welcome back! The subscriber who leaves the best caption for the picture below, in the comments section, will win the 25th Anniversary edition of "Who Framed Roger Rabbit" on DVD/Blu-ray, as well as a copy of the novel "The Great Gatsby"!


A few weeks ago, I was fortunate enough to have been invited to two separate events in the city that necessitated a slightly dressier wardrobe than I currently had in my size (Oh, so I suppose it's my fault I found a Dunkin Donuts that serves 50 cent donuts after noon? Wait. Don't answer that.) I had also completely spaced out and forgot about my weekend in the One Percent, and though my boyfriend was kind enough to send me a reminder the day before, it still left me with no time to venture out to my usual go to joint in the suburbs for nicer dressing (why, oh why can't we get a Kohls downtown?) I was also running into the following problems:

  1. Rent/other bills were just paid two days beforehand.

  2. Best friends' wedding the week after including expensive tux rental/hotel/gift

  3. It was Thursday at 6:00pm with the first event happening the next day promptly after work, leaving me about 4 hours to search before getting my little needed beauty rest.

The Mission: Find an outfit appropriate for a night at the opera (the Lyric Met actually, for preview night of "Oklahoma!") and a 1920's-themed party for "The Great Gatsby" at Untitled, a speakeasy downtown. For 50 dollars or less.

I knew a trip downtown was out, and I wasn't about to trek out to the H.I.P., so I reached into my memory bank and remembered the word that would save my hide. Ragstock. And Hollywood Mirror. Alright, 3 words. There are several locations throughout the city, but I knew I could go to Native Foods for dinner after visiting the location off of Belmont, so off I went.

My original plan was to find a suit jacket for Oklahoma, and just ditch the coat for Gatsby. As it turns out, guys who wear a size medium don't ever get rid of their outfits, and since my hemming skills leave much to be desired, the suit jacket was out. Vests are still a fashion thing though, and luckily, I found a super nice one at Hollywood Mirror in dark blue for $12.00. I ended up using this for both events, and I'll probably use it a few more times for the upcoming Wedding Season. I also picked up a snazzy "Newsies"-style hat for "Gatsby", also just $12.00. This isn't exactly multi use, but it meant I wouldn't have to do my hair.

Downstairs at Ragstock, I hooked myself up with two pairs of designer pants at 5 bucks a pop (which are SO going to be used for work), and a Calvin Klein dress shirt on sale for just $6.00. I should mention at these sorts of places, there's a no returns policy, so you should always, always, ALWAYS try the clothes on first. Even though they may be labeled as your size, depending on what year they came out and what brand they are, a 35" waist could actually end up being a 2013, 32". This rarely ends well for you, or the pants.

So how did it all turn out? Let's add it all up! Two dress pants, one dress shirt, a hat, and a vest for only $45.42 including tax. Considering the majority of these can be worn for multiple occasions, I'd consider that a success! Need proof? Ask Michigan Avenue Magazine.


Photo by Daniel Boczarski/Getty Images for Michigan Avenue Magazine


Filed under: Budget Tips, Giveaway


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  • fb_avatar

    Photo caption: "Extra, extra! Hipsters guzzle phosphorus tribromide in mass confusion!"

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    Please take me shopping, oh wise one!

  • fb_avatar

    Extra! Extra! Read all about it! Gay man somehow able to dress himself under $50 & still look FABULOUS!

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