23 ways a Lindy Hopper can up their menswear game

Dressing well is form of good manners. – Tom Ford

One wonderful thing about being a swing dancer is that often times when you get infected with the dance bug you often also find yourself wanting to invest a little more in your style. Shine your shoes and slick your hair, so goes the song by Fats Waller. You want to look the part. Dressing nice is one more piece in the puzzle of how to bridge the gap between old photographs and video footage — and yourself. Dancing and fashion — they really do go hand in hand. Vintage clothes are wonderful, but you can also find ways to accent your style with modern, but classic fare as well.

Teaching, going to dances, pictures of yourself on Facebook… all good times to looks your best. If you’re reading this, perhaps you’re interested in dressing a little better. If nothing else, looking a little more dapper in all those years of pictures is going to pay dividends for a long time to come.

It might start with a new shirt, or a new tie, or dusting off an old suit that you saved exclusively for weddings and funerals (most likely from your pre-dance years). Once you put a little more effort into your look, all of the sudden more people ask you to dance. You seem somehow more trustworthy. People notice. Your confidence level goes up. It’s a self-perpetuating cycle that fuels your dancing.

Now, some of these tips below might be old news to you, but they took me a little while to gather and put to use for myself. Enjoy!

1) Decide what “fashion” means to you

A good first step in being fashionable is to decide what “fashion” is to you. Luckily, there is an amazing tool for this called Pinterest. I sat down for few minutes a day for several weeks and decided exactly how I would dress — if I were to have unlimited funds and time. I came up with this ever-growing pinboard of awesomeness (to me). Feel free to borrow any part of it for your own, but make sure your inspiration board speaks to you. First rule in dressing well is that it needs to accentuate “you”.

Follow Daniel Newsome’s board Men’s Fashion on Pinterest.

Whenever I feel tempted to buy a new piece, I ask myself if it would fit in this board. If not, it’s not on my style-path, and I leave it for the next person.

I’ve also found some wonderful Instagram accounts that I follow for ideas.

2) Natural fibers are your new go-to

When I first started working on my wardrobe, I couldn’t (or didn’t) discern much between different kinds of fabrics. Now, my goal is to go with wools, cottons, etc. It makes a huge difference in how the fabric lays against your skin, how long it will last, and how well it compliments other fabrics. Synthetic fabrics are your new enemy. In fact, there is a triad of good dress, it goes Fit, Fabric, and Flair (more below). Choose wisely.

3) The rule of the “statement piece” aka “Flair”

“Totally pulling it off”

In every good outfit, there is one (and not usually more than one) statement piece; this can be a fancy tie, a pocket square, cool glasses, a killer hat, a unique jacket, or even crazy socks. If you do more than one statement piece, it’s not against the rules, but your outfit will be “dandyish”. Not a bad thing, but it pushes it into the realm of costume. It’s advanced stuff that you need to curate clearly. Personally, I like to have one standout item per outfit.

4) Glasses

If you wear glasses, go classic. Warby Parker has tons of nice classic styles, and they will even send you five frames (for free!) to try on and see how they fit your face. If you don’t wear glasses, you should consider having 3-5 pairs of classic sunglasses that perform two functions. 1) Sunglasses have always been a staple of cool. 2) Wear regularly, they will save your eyes a lot of sun-related aging. I never step outside without sunscreen and sunglasses.

5) Wear things that fit

Lots of men wear clothes that are WAY too big, distort their body proportions, and generally make them seem strange and unfashionable. If you learn your measurments you can buy online a lot easier. Here’s a couple of guidelines:

• Where the sleeve starts on your shirts should be the point of your collarbone. Don’t let your shirts or jackets be too wide.
• If you can fit more than two fingers in the waistband of your jeans, the jeans are too big
• When in doubt, tuck in your shirt.
• Google “collar gap”, learn what it is, and try to never have one.
• If the shoulders of your jacket makes little bumps, it’s not a fit.
• If you are going for vintage with a suit jacket, watch out for cuts or tailoring that pulls it in at the waist and gives it a more fitted look, unless you want the modern fit on purpose. Vintage jackets fit square, without a collar gap, and just wide enough to fit, but no wider.
• Tailoring is thing that well-dressed men do. It can turn a closet full of things you never wear into a bunch of pieces you wear all the time, so it’s quite worth it.

6) Learn to tie a tie a few ways

Ties have different fabrics (obviously), what isn’t obvious is that a small tie knot can look dorky. If you know a few alternate knots then you can make a more appropriate and substantial tie knot for yourself. In addition, you never want a tie to extend below your belt; it looks like you are in one of the earlier seasons of “Friends”. It should hit right at the top of your belt, or higher for some vintage looks.

7) Ditch coats and sweaters with zippers

Zippers on sweaters and coats are…tough. There’s a couple of notable exceptions, like 50’s cut jackets, but on the whole you want to go for nice buttons or toggles on both coats and sweaters. They will always be classic, and they never look cheap. Bonus points if the button is a natural material like wood or shell.

My favorite style of sweater is the cable-knit cardigan. Ben Sherman carries these, as does Banana Republic. Shawl collars are a great look.  Find a fit that doesn’t add bulk.

8) Acquiring ties

Ties are a mainstay of any man’s wardrobe. They can be pricey, difficult to find, and tough to match. My favorite technique is to search eBay for “vintage tie lot”. A “lot” is a group of a certain item for sale. Often you can get 10+ ties for as much as you might pay for 1 tie. If there’s a couple winners in the bunch you’ve done well.

9) How to size pants

When the time comes for your Pants Pants Revolution, keep these items in mind:

• Patterns will make your lower half look larger. Avoid them if you’re not a decidedly skinny person.
• Anything that tapers causes you to look more and more like an ice cream cone. That is bad. Very, very bad.
• Cargo pants should never be worn. Ever.
• If you aren’t actually on a beach or going in water, shorts are unacceptable.
• Denim is good, for a couple of days a week. Go for dark and classic. Dark is slimming.
• When vintage shopping, you can pick up a pair of pants, and with the front button buttoned, wrap them around your neck and if it fits around exactly, chances are that it will fit your waist.  This magical trick can save you a lot of time in the fitting room.

10) Shoe basics

If you’ve read this far, this is probably not necessary to say (though a few of my favorite follows have insisted that I include this) – but athletic shoes are no longer a part of your “going out” clothes. Dress shoes are a must, sometimes Keds for a performance. Dress shoes are one of the most important parts of your wardrobe.

When choosing your dress shoes, the perforations on the front are often preferable (for me). They are known as the “broguing”. The workmanship, perforations, stitching, and materials make a big difference in shoes. I prefer rounded tips as opposed to square ones.

At very minimum you need 4 colors of shoes in your closet: black, tan, brown, and oxblood (dark red). Other colors are great, but these are the minimum. The two brand I really like are Allen Edmonds, and Johnston and Murphy. Allen Edmonds are great because they can be serviced year in and year out, and while they are expensive up front, they will last longer than other economical shoe brands.

11) Tie clips and tie pins

They are a great touch to any outfit, and a good place to find them is Etsy. I search for things with initials, or “deco” in the title. They’re great conversation pieces, so things with ships, anchors, etc are really nice.

12) Be bolder with textures and patterns

One thing that can be challenging when going from the boardroom to the ballroom is how to look “nice” without looking “corporate”. Mixing up patterns and textures are key to this. Houndstooth, gingham, vertical stripes, patterns, etc are great for mixing up. Chances are good that you (like me) have a very conservative comfort zone.  The bolder you get with this, the more you are going to stand out- in a good way.

13) Custom shirts

One of the best ways to build a wardrobe that will last decades is to invest the extra money in custom shirts. I recently upgraded all my shirts to be custom, and it has really changed my wardrobe for the better.  I used to have 50-60 cheap shirts I didn’t like all that well.  Now, I have 15 I love.  If you are interested in looking at custom shirts, click here for a $20 Trumaker Credit -> Credit

14) Learn your hats

Hats are tough.  They will also make or break an outfit.  Fedoras are classic. A Fedora done well is good; done well is also hard. Done poorly and you’ll look like Indiana Jones.

Tilt makes all the difference

A big brim is… adventurous

There are two kinds of newsboy caps. One is an 8 panel, and one is a “flat cap”.  For my money, I like the 8 panel a lot better.  Prohibition Clothing Company has some wonderful 8 panel caps.  Not cheap, but it’s the only one you’ll ever have to buy.

15) Learn your own colors

Everyone has certain colors that flatter them.  Everyone has things that look better on them… that’s a given.  Finding what your colors are is key, and it’ll make a huge difference in how you look, and how people react to you.  There’s a story often told by Norma Miller, that the reason Frankie never won the Harvest Moon Ball is because he always wore a suit that was too low-key (his famous brown suit). Ask around. Ask your fashionable friends.

16) Tan is not brown

This took me a while to understand. Early on when I started trying to dress a little better, I learned to never mix grey and brown.  It took me a few years to realize however that tan and grey are a great vintage combination.  Because tan is a color, where brown is a neutral.  This is the kind of thing that can really make you look good AND vintage… not just good.

17) Socks

Never wear white, unless you’re dressing exactly like Gene Kelly and you can dance like him too. Striped socks are classic. Polka dots are quite in fashion nowadays. It’s one of the easiest ways to trick people into thinking you’ve got an exciting personality.

18) Proper undershirt

The undershirt has come so far. You don’t need to have a bulky undershirt that shows underneath your shirt.  If you are leaving your collar open, wear a v-neck shirt.

Also, if you wear A-shirts, call them A-shirts.  Don’t call them “wifebeaters”.  That’s just not nice.

Here’s another trick: Don’t match your undershirt to your outer shirt, match it to your skin tone and it’ll hide the lines of the shirt.

If you do a quick Google of “Invisible Undershirt” you’ll see some fantastic options

19) How to roll up a sleeve

There’s two ways to roll up a sleeve. The obvious way leaves you with a sleeve that can sag. The other, less obvious one is a cool way to keep the sleeve up and gives it a cool bit of the end peeking out.

Instead of rolling your sleeve up one cuff length at a time, pull your cuff inside out and just past your elbow, then double up the lower half.  For details, see this video:

20) How to tie a bowtie

Bowties are currently in fashion and quite fun to wear. I’m a fan of only wearing self-tie bow ties. This is a good, short video on how to tie one.

21) How to choose a pocket square

Pocket squares are an awesome way to jazz up an outfit. They are designed to “accent” the tie, not match it. If you match them exactly, you’ll look like you bought a cheap ensemble at a men’s outfitting store. Even if it wasn’t cheap, it’ll come off like a rented tux.

Estate sales are great for these.  New pocket squares can be upwards of $50!  Estate sales and vintage stores have great pocket squares that compliment your outfit and are swing era appropriate.

22) Bleach washing

As I got to the end of this blog, I started asking my follow friends if they had any tips.  From more than one of them, I heard that leads often have a “mildewy” smell. Eew. That’s never good. Washing your white clothes with bleach, and moving them directly from the washer to the dryer can help you avoid this smell. Never wear dirty clothes.  That’s just rude.

23) Match, but not too much

It’s nice to match. But remember that three colors are often better than two, and if your shoes match your belt and your socks match your shirt you end up looking more like a cheesy superhero rather than an effortlessly fashionable gentleman who just so happens to look great no matter what.

For instance, we’ve all heard the rule about matching your belt to your shoes. This is a nice one, but it’s quite cool to mix them just slightly off-shade.

Last but not least, remember that clothes are just a way to share a little bit about “you” to the world, so with everything in your closet, if it doesn’t make you happy and feel like “you”, pass it along or trade it for something that does feel like you.

It takes time to build a good wardrobe.  I’m still working on my wardrobe, and will be for a long time, but it’s a fun journey and one that you won’t regret.

Post your tips and tricks below.