Men’s Vintage Clothing – Styling and Shopping List

mens fashions 2Hello Fellas,

The good news is vintage clothing for men is becoming much easier to come by these days. The bad news is it can be hard to distinguish what pieces will be worthwhile additions to your existing wardrobe. Before you purchase vintage pieces it is good to consider a few important things:

Manliness & Fit: Take it from a woman, the worst thing is when a guy is trying to pull off vintage style and he looks too feminine or like he should be wearing things in a size up. There is a fine line between form fitting vintage clothes and vintage clothes that are too tight. A few signs a piece may not be for you is if:

  1. Your “package” is creating a prominent bulge in your pants (not in a good way). In short, your pants look painted on. 
  2. You try doing a minimal stretch and the shoulder area in your jacket feels too snug. Test movement of the piece. 
  3. Your wrists and ankles are very exposed when wearing full length garments. (Note: it is okay if they are showing a little) 

Try Mixing & Matching: Vintage clothes can age you if you don’t do it right. Wearing too many pieces of older clothes can in fact make you look older, especially if you already have a thick beard and larger glasses. The key is to not hide behind the clothes or let them weigh you down. Vintage pieces should be mixed with a few modern pieces to give you that overall sharp look. 

Suitability: Understand what suits you! Some people (myself included) can’t pull everything off. Know your proportions, existing style and plan accordingly. Ex. I look terrible in large sunglasses because of my face shape so I generally just don’t wear them.

I know it sucks when you find only one of something in a store and you try it on and it isn’t 100% what you hoped but sometimes you have to just put it back.

Now that you have digested a few style considerations why not add some vintage staples to your closet. Keep in mind when purchasing some of these it may be worthwhile to splurge on select pieces as you could have them for a lifetime.

Vintage clothing shows such as the one coming up in Ottawa this weekend may be a good place to start.


Jackets & Blazers:

Biker Style Leather Jacket: Should be black or dark brown with a bit of a worn/distressed look. Should not be longer than your torso and should be zip up with a high collar.

Military Style Trench Coat: Should be cotton, not pea coat material. Double breasted is your best bet! Burberry made some awesome coats in the past. Don’t forget to make sure it has its belt. I went to a few vintage stores lately and the trenches were missing the matching belt. Full length coat only. If you prefer a more polished look rather than casual pull a Don Draper (from Mad Men) and go for a high-collared tan trench that’s a bit more refined.

Barbour Wax Jacket: You can usually find them in a variety on cool colour combos. Be picky about the number of pockets. Too many pockets overpowers this jacket. Check for holes in the pockets and any re-stitching.

Tailored Tuxedo Jacket – A black satin lapel is always nice and allows this jacket to be versatile – easily dress it up or add some dark denim and dress it down. There are some nice wool blend tuxedo jackets out there. Some people love velvet ones however keep in mind velvet is kind of heavy so not ideal to wear in all seasons.

Timeless Tweed Jacket (with elbow patches): These jackets look smoking hot in a darker brown or deep blue colour. Obviously they are woven with other colours to make them appear a bit lighter. The darker the blend the more this jacket will make for a good evening look.

Shirts & Sweaters:

Plaid Flannel Shirt: Go for a long sleeve traditional flannel shirt. Try something a bit different and casual Friday appropriate and aim for no Christmas colours if possible.

Denim Shirt: Long sleeve only! Can be paired/layered nicely with flannel.

Band T-Shirts: Black & White band shirts are classic. It is also okay if there is a bit of fading, it just adds to the look. New can be overrated and doesn’t add that vintage vibe. Authentic T’s are always rockin.

Chunky Knit Crew Neck Sweater: Any colour. It is also a good layering piece. You could also try a Cable Knit Sweater. Get a colour that brings out your eyes and goes well under some of your work button down collared shirts.

Carefree Button Up Cardigan: These are so versatile and can go over dressy shirts or more casual shirts. The lighter the better than you can layer more. Go for standard colours like beige, black etc. so you can pair with more pieces.

Fun Times Fair Isle Sweater: Go for a fun knitted one with a bit of character. This is better for the Spring, Fall and Winter. Its a good conversation piece at a party. All the ladies (and men) will likely bring it up while chatting with you.


Jeans: Go for a slim straight leg pant. Dark washes are preferred! If you are going to get lighter vintage denim stay away from a long zipper crotch and high pockets on your butt.

Thick Chinos: Also try and find a straight leg. These pants look great in tan or navy.

Looking for a full ensemble?  Pair these items above with a pair of Brogue or Chelsea boots and you are good to go. Come back for more next week on men’s vintage accessories – ties, hats and sunglasses oh my.


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