Men: How to Pick Your Tweed Ride Clothes

For the guys out there gearing up for this Sunday’s ride, the majority of you fall into two camps:

1) The traditionalist. You revel in the finer things: barrel-aged whiskey, leather/suede (no synthetics!) elbow patches, honey brown Brooks saddles, knickerbockers, and books with pages that smell like musty libraries. You see this as your excuse to show off what you already have, and you figure: “Well, I dress like this anyway.”

2) The guy that looks into his closet and thinks “Uh… I think I have a tweed vest?” You can’t tell Houndstooth from Herringbone, and the only Bird’s Eye your familiar with is in the freezer aisle of your local bodega.

This post is for you both. We love seeing the eclectic styles everyone puts together for the event, but as time winds down we know many men are scrambling to assemble the perfect outfit, so we’re giving some tips on how to ensure you look good and feel good in whatever you decide to wear. Our first tip: don’t think of it as a costume.

While we are paying homage to past styles, the well-dressed man is a timeless being. A well-fitting jacket or waistcoat will do wonders for a man’s posture, which is helpful while riding and definitely makes you look more confident. Fit is key when it comes to putting together an outfit, and you should pay more attention to how a garment hangs off your body than wondering whether or not you’ll look “authentic” enough. Dandies & Quaintrelles isn’t a historical society, it’s a supreme being of leisure.

The basics:

Jackets should fit perfect at the shoulders. This means the arm seam should begin at the exact point where your shoulder ends. Any more than that, it’s too big and you shouldn’t buy the jacket. When you put on the jacket, the ends should hang no further than halfway down your hand. If you prefer a slimmer silhouette, chances are the jacket will be cropped, and will hang a hair above where your thumb begins. The latter is a better look for shorter men or guys with shorter torsos, as it makes you look taller.

Lucky for many of you, tweed is in this season. The tweed jacket — while not really necessary — is still a very versatile wardrobe staple. Pair with a hoodie or denim jacket underneath to make it seem more casual, and it goes great with a pair of slim dark jeans or plain-front chinos. Tweed’s timeless nature has made it so it never really goes out of style, just fluctuates in popularity. We gave you a look at some vintage stores to check out, but here’s some retailers with their own offerings:

  • Gap’s Wool Blend Herringbone Blazer combines affordability and a classic look for a piece that is sure to transition well between the Tweed Ride and the workplace.
  • J. Crew’s solid tweed Ludlow Sportcoat comes with thinner lapels and a slim-fit to modernize the jacket, the muted pattern and blue color is both versatile and unique. In a sea of browns and greys, you’re sure to stand out. $265
  • Banana Republic’s Wool Herringbone Military Blazer adds epaulets and flap pockets to the traditional blazer, giving it a more rugged look. Combined with a surprisingly improved fit this season as well as a revolving number of discounts, this could be worth your while. $250
  • Rugby’s Newbury Tweed Blazer is for men who want serious quality and fit. High armholes, silk trim, and an oxford lining make this one of the ultimate prep pieces — if that’s your thing. Quality has its price though, but hey, you need to splurge every now and then. $498

Waistcoats are also a very popular alternative for guys who don’t want to look too buttoned up, and with the forecast this weekend it’s shaping up to be a great alternative. You’re gonna need to pay more attention to how your shirt fits. So that means slim it up, you don’t want a well-fitting vest ruined by a blousy shirt underneath. It doesn’t have to be skintight, but again the shoulders should be in line with — oh forget it. I’ll let the dudes at GQ field this one:

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If you don’t have a three-piece suit, I’d recommend getting one, it’s a great investment and can be worn in a number of ways. If you’re hard-pressed to buy a vest though, here’s a few worth checking out if you end up striking out at the vintage and thrift stores:

Of course, H&M always has a steady stream of very affordable offerings. I have a herringbone three-piece suit that’s lasted me years. If you don’t wear suits often, the Swedish retailer has a plethora of choices that fit great and won’t leave your bank account slim.

Pants-wise, slim, dark jeans are great, as are fitted chinos and trousers. It’s very trendy right now to cuff your pants a little, but if you’re wearing trousers you usually want very little break — that is, minimal bunching of fabric where the pant hem meets the shoes. Speaking of shoes…

The shoes: you want a safe bet? Wing tips. They’re very classic, yet of the moment, and the broguing (the little holes you see poked around the shoes)  helps a little with air flow. They were originally meant to help drain water out the shoe for a lot of the rugged Europeans that used to sport them on muddy farms and fields (and still do).

Florsheim Kenmoor. $225 at Zappos.

The best part is many of these are available in vintage and thrift stores. Dr. K’s vintage has a bunch for reasonable prices. Other great alternatives are saddle shoes, plain oxfords, and brogue boots — which seem to be having a moment.

How to know when you’re getting a steal on vintage shoes: these tried and true brands have lasted for hundreds of years due to their painstaking attention to detail and quality construction. If you find them at or below the following price ranges — and they fit, of course — they’re definitely a worthy investment.

  • Alden is one of the great American shoemakers, and have their own store in downtown DC. Their styles range from the classic 405 boot — nicknamed the “Indy” boot due to the character sporting them in all the films — to more classic American staples like bluchers and oxfords. These are a steal anywhere from $100-$250.
  • Allen Edmonds is also a traditional American shoemaker, and you can find their DC store in the Golden Triangle area. They’ve been putting out saddle shoes, wingtips, and monk straps for a long time, and while they’re not all the rage with the kids these days like Alden, they still have a dedicated following. These are readily available in thrift stores and on eBay for $30-$90.
  • Florsheim still makes great shoes, though currently they’ve been getting a lot of buzz for their collection with designers Duckie Brown. That line features classic designs with crazy colors like electric blue and silver, but you can find plenty of Florsheim Imperial shoes online for about $25-80.

Don’t be afraid to accessorize: throw a scarf under your blazer, wear a walking cap or cabbie hat, put on some fun socks to flash while you pedal. The main point is to have fun with the old stuff.

Parting shots: Ok, enough with the advice. For your inspiration: men who got it right.

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