A quick and dirty guide to dapper sir-ology 6

Since these are questions that a lot of my fellow dapper sirs in training seem to have, handy-dandy post ahoy!

Where can people with breasts/more classically female proportions get shirts that actually look like masculine shirts instead of winking teehee don’t worry these are still ladyshirts?

Number one, hands down, you want to refer to Saint Harridan. This store was made for you. Bonus points because they have a wide range of sizes. This is where you can get shirts, as well as suit pants (made masculine style, with real suiting) and suit jackets. Right now they just have two piece suits, but they’re developing their vests at this moment so I expect there to be three piece suits in our future as long as we keep supporting them.

Anyway, the Saint Harridan shirts are excellent, and are cut and quality equivalent to good men’s dress shirts, down to having real collar stays. This is invaluable if you want to wear bow ties in particular, since a stiff collar is going to work a lot better with them. The only downside to Saint Harridan shirts is that they require ironing.

Dapper sirs iron their own shirts. True fact.

If you can’t afford Saint Harridan or can’t handle the thought of ironing, you can also try Brooks Brothers or Charles Tyrwhitt. Brooks Brothers classic fit or semi-fitted shirts will get you about the look you want, and they are significantly cheaper; if you wait for a sale you can normally get a shirt for $50-$80 per, which trust me is pretty good for a dress shirt. They also sell noniron shirts, which is a bonus.

Down sides: Sizes will not go above 16 US, since most of America apparently believes men of all sizes deserve decent shirts but women don’t. (Though per Rosemary, the Tyrwhitt shirts at least in the UK are cut so that they favor big chests and not terribly broad shoulders; try before you buy or be prepared to return things.) They are still definitely women’s shirts, so the buttons are on the left side and the buttonholes are on the right. Also, sad, relatively floppy collars with no stays.

What about trousers?

Saint Harridan will have your best trousers. Again, these will be cut like men’s suit trousers, which means pockets. REAL POCKETS. Pockets you can lose your wallet and cell phone in. You will never be able to look at another pair of shitty women’s trousers the same way again.

Failing the money to invest in the amazing Saint Harridan trousers, I recommend Brooks Brothers. You want to ask for a style called the “Flow.” I know for a fact they come in black and charcoal gray. I use those as my work trousers, actually. But they do not have real pockets, alas and alack. I also recall finding okay-ish trousers at Banana Republic at one point, though from the men’s side my BFF Mike was not impressed by the staying power of their clothing. Tyrwhitt might work, but I can’t speak from experience. Also, none of these places have any love for someone who isn’t a women’s size 16 or smaller.

Basically, you want something that’s decent suiting, which will probably be wool. If you don’t have to dry clean it, those trousers ain’t good enough for you. Don’t ever get linen unless you both hate yourself and love ironing.


Unless you’ve got a build that meshes well with men’s clothing, buying one off the rack and having it altered doesn’t work out so great. For mine, I ended up going to a local tailor (Martin Tailors) and paying them to custom make a pattern for me from a classic men’s vest. And I paid out the nose for some really good designer fabric. (For fabric, try places like Mood Designer Fabrics.)

Saint Harridan now does have their vest patterns up and running, and I’ve been pretty pleased with the results. They tend to do their more specialized clothing in limited lots, so keep an eye out for when they are selling vests.


Whatever you end up buying, take it to the local tailor and spend the money to have it tailored. This will be extremely necessary for anything from Saint Harridan, because the sizes will come close to what you want off the rack, but everyone’s body is unique, and if you’re going to pay $900 for a suit you want it to fit you perfectly. Tailoring is worth the money, trust me.

I’ve also taken Brooks Brothers shirts to the tailor before just to have the button positions adjusted so the sleeves will sit right at the cuffs of my jacket. Little details make a huge difference.


If you have women’s size 10+ feet, you’re in luck. Get men’s shoes. I have size 10-10.5 feet (US), so I fit well in a men’s 7.5. Men’s Wearhouse will be able to take care of you for a decent price. I have never gotten a pair of dress shoes I liked from places like DSW, I will note.

If you have smaller feet than mine, maybe boys dress shoes from places like Nordstrom would be a place to start. Also, per Bogo-lode, if you know the style you want you can sometimes find the smaller men’s sizes (5-7.5) on Zappos. There’s also Tomboy Toes, which is specifically for men’s shoe styles in women’s sizes. (Which means everything they have is too small for my feet.)

Black Oxfords are always classy and will make you feel like a million bucks when you wear them. Get yourself some parade gloss shoe polish and keep those babies shined.

As an alternative, depending on the look you’re going for, you might be able to rock a pair of boots like Doc Martens, so long as you’re keeping them appropriately shined. Technically speaking we’re already challenging fashion norms by not wearing designated ladyclothes on our apparently female bodies, so we can get away with being a little more playful.

Other accessories?

Get yourself a leather men’s belt, since that’ll be wider than a women’s belt most of the time. Men’s Wearhouse will have almost any waist size, and the most common leather colors. Make sure your belt and shoes match.

Okay, so ties. What about ties?


Ties are actually the easiest part of this equation, because a tie is a tie is a tie is a tie. You can get them anywhere ties are sold. I actually prefer Men’s Wearhouse for my tie shopping over a place like Brooks Brothers. (William Henry Morris on twitter suggests the Tie Bar as well.) Men’s Wearhouse will have the whole array of colors (normally arranged helpfully in a spectrum by shade) and will have patterns that vary from conservative to downright playful. Somewhere like Brooks Brothers will just have more conservative color and pattern options.

Quick points:

  • If you have a wider body like me, wide ties. If you have a narrower body, skinny ties.
  • Pay attention to if the tie says it’s extra long or not. Generally, unless you’re very tall or have a very long torso, you do not want long ties.
  • Bow ties are not scary. Buy a good bow tie. You will thank me later.
  • If the tie is longer than works with your body, just keep the excess length in the skinny tail. You can then tuck the tail into your shirt at the stomach. If that makes your tie sit a little funny, you can compensate with a tie clip.

But tying ties how work?

It’s not as scary as it sounds, I promise. I have almost no hand-eye coordination and I manage. Here is your basic bible. Live it, love it, never be afraid to pull it up and double check.

And honestly, I’ve hit the point where I tie bow ties faster than regular ties, because even if the knot is slightly more complicated, you don’t have to fuck around with getting the tail length right.

Get your the dimple for your tie set up when you are tightening it down. It looks nice. I’m not a fan of having super Criminal Minds-tight knots (I always feel like Hotchner and his tie are locked in some kind of ongoing death struggle), but that’s a style thing you should decide for yourself.

If you have a really wide collar, use the wider knots, the Full Windsor or Pratt. If you have a narrow collar, which you probably will, you want to use a Half Windsor or Four-in-Hand. I prefer the Half Windsor because I like my knots symmetrical. The Four-in-Hand will give you an asymmetrical knot that makes your look a little more casual, so your mileage may vary. Also note that the Half Windsor will take up more of your tail in making the knot, so if you’re trying to eat up tie length, that’s a thing to consider.

Bow ties work best with stiff collars that have stays. That said, I make them work with floppy-collared women’s Brooks Brothers shirts all the time, mostly because I can wrangle the collar by wearing a waistcoat. It’s not the best, but it works.

And a word about laundry.

For your good suiting: make friends with your local dry cleaner. Follow the directions on all of your good clothes. Take care of them and they will take care of you, promise.

That said, you don’t have to visit them nearly as much as you think. Dry cleaning is rough on clothing, and should be used sparingly. Basically, it’s what you do when brushing and airing out your suit/vest/trousers no longer does the trick on making them wearable, or when spot cleaning isn’t going to cut it. So this is all going to depend on how hard you are on your clothes, how much you sweat, and how badly the BO fairy fucked you over in puberty. If it’s still stinky after you’ve let it air out for a couple days, then yeah, probably time to go to the cleaner. If not, you’re good. (It’s also been suggested by William Henry Morris on twitter that unscented Febreze does wonders in this regard.)

For your shirts: most dress shirts can be laundered conventionally. To be honest, I would discourage you from buying a shirt that can’t be thrown in a washing machine at home, because unlike your suit, you’re going to want to launder that after every hard wearing. Noniron shirts, take out of the drier immediately and hang; they should be good to their word and not need ironing. If you let them sit in the dryer and get a bit wrinkly (or if you’re unpacking them from your luggage), you can either iron them, or throw them back in the drier on low heat for ten minutes and hang them up after. That’ll normally take any wrinkles out.

For shirts that need to be ironed, just do yourself a favor and iron them directly out of the drier so you don’t suddenly have a mountainous stack of wrinkly shirts, piteously calling your name into the night.

And for god’s sake, iron them for real. None of this collar/cuffs/pocket/placket only nonsense. Yes, it will get wrinkly as you wear it. No, it will never get that wrinkly unless you’re planning to roll yourself up in a ball and stuff yourself in an overhead bin.

Any basics I missed? Feel free to ask!

6 thoughts on “A quick and dirty guide to dapper sir-ology

  1. Reply JohnD Oct 25,2015 13:26

    OK, I am till trying to figure out what the deal is with pockets. I mean, yes Delaney covered that in The Fall Of The Towers but still, what the heck!? Haven’t fashion designers figured out tht women want pockets yet?

    New plan for taking over the world: sell high fashion clothing *with* pockets. Heck, just pull a Richard Prince and copy other designer’s lines only add pockets. Then ssit back and let the money roll into your pockets.

    • Reply Rachael Oct 26,2015 11:21

      See also: The Gender Politics of Pockets

      This is something that comes up every year on Project Runway, actually. The designers continuously assume that women a) shouldn’t have to wear bras and b) don’t need pockets. Whenever someone actually designs a garment that has pockets, or that a woman could wear a bra with, they almost always get called out for special praise.

  2. Reply Guy Middleton Oct 26,2015 21:57

    Wearing men’s shirts gives women the opportunity to indulge in the only male-only piece of jewellery — the cufflink!

    Ok, so it’s not the only one, you can wear a tie clip too…

  3. Reply Devin Smith Apr 26,2016 20:49

    Tyrwhitt cuts their shirts very differently in the US and the UK. I was a loyal customer for years in the UK, and was in New York and saw their retail location so I stopped in to get some shirts. Without thinking, I ran in and grabbed a couple shirts in my size.

    Those shirts, I kid you not, were about 16″ bigger in the waist than the same size shirt in the UK.

  4. Reply Geri Sullivan Aug 4,2017 20:51

    Alex, I just read this fabulous column nearly two years after you wrote it and am heartbroken to follow the link only to discover that Saint Harridan is closed. The statement on their website is a thing of beauty. While I am far from a dapper dresser, I would adore a couple of outstanding pairs of good trousers with real pockets.

    And, as a side note, as fans across the globe are heading to Helsinki, let me thank you again for your docent tours of Fandom Rocks! in Kansas City last year. I loved bonding with you over rocks.

    • Reply Alex Aug 6,2017 07:43

      I need to update this to reflect that bit of sadness. I’ve been in denial a bit since I don’t know where the hell I’m going to find this sort of clothing again.

      I’m really glad you enjoyed it! I had so much fun talking about rocks with everyone. :)

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