Old (Vintage) Clothing Can Make a Man Better Dressed!

What to Do When You Are Suddenly Single and There's Nobody to Dress You?

Richard Davis
Gentlemen, you've been dressing yourself for years, decades.

Right? True?

No. Not exactly.

Most men gladly heed the advice of the women in their lives when it comes to wearing anything more than jeans and t-shirts. Most of us are clueless when it comes to mixing and matching shirts with pants. And let's not even go to suits and ties!

The shirt on our back is not given much of a thought until we end up without help in choosing the next one. This can happen through divorce or the break up of a long term relationship. Then we are lost. Lost in a confusing forest of clothes racks, natural and synthetic materials, and bewildering colors.

Being suddenly single can become a clothing emergency!

Dressing well is not an option.

You need to pull it together and dress smart. Your job demands it, and if you ever want to have any hope of finding another lady in your life who might help you with your clothing selections, you've got to be looking good.

Here is where what you wear can be old and be new again. Here is where you chose retro.

Clothing costs. It can drain you of Franklins faster than support payments. One solution is to go back in time and pick up some nice duds from places that specialize in older or "vintage" clothing.

My first experience in vintage clothing came not long ago. It is true that I do own socks that are older than Justin Timberlake, but I'm speaking about a real enlightenment on my part. I recently added a vintage overcoat to my wardrobe. It is wool and gabardine and was solidly stitched over forty years ago. It has a real heft and quality about it. No loose threads or frayed edges. It was made in the USA to boot!

Not long ago I visited Night & Day Vintage, a little shop in Chicago on Belmont, that has a nice selection of men's vintage clothing. I saw a couple of suits priced in the $85 to $125 range, some with two pairs of pants. I saw 1950's shirts and overcoats. And shoes! Yes, vintage shoes.

Dudes, here are the reasons to get old when it comes to clothing. You can do it on a budget and you can look unique. You can stand out in a crowd. You will perhaps catch the eye of a discerning woman who knows what good taste is and has a bit of the romantic in her.

At Night & Day Vintage you can also pick up something to top yourself off with: a vintage hat. Pick an "Untouchables" style, a fedora, and even a pork pie hat.

If you are nowhere close to Night & Day, and you have no plans to move to Chicago, try local thrift shops and even the Goodwill , which generally has a couple of locations in larger cities.

Another source is garage sales. You will get really motivated sellers here. Nobody wants to haul racks of clothing back inside. Estate sales offer another opportunity.

Suppose you don't want really old clothes, but you want to look like you have some class and a sense of romance and history about yourself?

There are a growing number of online stores and shops that can outfit you in styles that recall an earlier era.

There are shows in Chicago and St. Paul that will feature many dealers in vintage clothing. The next show in Chicago is February 22 & 23, in Elgin, Illinois.

Finally, the best place to look might be your parent's attic. Chances are, if you are suddenly single you might be stopping back at mom and dad's for a home cooked meal.

Skip dessert (in order to keep fitting into that vintage clothing) and climb the stairs to the attic.

You never know.

This is where I found my nice new forty-year old overcoat.

Published by Richard Davis

Born and raised in Chicago. Traveled a bit. Lived a little. Miles to go.  View profile

  • Night & Day Vintage in Chicago can dress you in style for yesterday's prices
  • Sources for vintage clothing
  • Upcoming vintage clothing shows
More and more younger men are wearing styles that reflect a prouder past in America. This means the smart set is dressing the part and looking very much like an old black and white movie, wearing enduring styles and clothing that makes a unique statement.

2 Comments

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  • Richard Davis1/23/2008


    I did email to Jolie. I hope some locals will visit her store.

    Yep, I'm dressing up the old bacon and stepping out. Well, let's see, vintage clothing in Wisconsin? It's the old red long johns with the trap doors in the rear. I think I might pass on those. lol Some old bibs? Why not? Farmer Rich.

  • Baconator1/23/2008

    Oh no.. Rich is getting all flashy on me eh? LOL! Great article.. Oh and Goodwill and garage sales rock!!!! I will keep my eye out for some nice vintage clothes for you here... wonder what they consider vintage? Blue jean Bibs????

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