How to Play Blue Suede Shoes, and More Style Dilemmas Solved

You send us your most challenging wardrobe quandaries, and our team of fully licensed Style Experts™ does its best to steer you right. This week: The right way to wear blue loafers, Shirt Tucking 101, and how to class up your streetwear steeze.

Hey, I just bought some blue loafers from Tod’s—fell in love with them at the first sight—but I’m having difficulty in matching them with my wardrobe. They’re a Munsell Blue type of color, and is very striking… any ideas on what to wear them with? Jeans? LOL
Dude, no need to LOL. A blue pair of Tod’s (like the ones here), can look great with a nicely faded pair of jeans, or a pair of straw-colored chinos. Or, for the full off-duty-in-St. Tropez effect, pair ’em with slim white jeans and a navy blazer. Just avoid getting too matchy-matchy; embrace the color’s outlier status and pair it with complementary hues. The key is to wear them with confidence, and a dressing-by-numbers approach will undercut your swagger faster than an unzipped fly.

And props on following your gut. Too often, guys will balk at buying something they love until they can picture it fitting into their existing wardrobe. It’s a sensible approach, but if you don’t keep it in check it can also be a fast track to a serious sartorial rut.

From a gent from Illinois: Can you effectively turn a barrel cuff shirt into a somewhat “french cuff” shirt by taking the buttons out and using cufflink to attach them? Or will this be seen as incorrect like wearing a watch that doesnt work.
Can’t say I’d recommend doing either, but I’d wear a broken watch before I’d wear cufflinks with barrel cuffs. (As the saying goes, even a broken clock is right twice a day.) If you’re trying to project a little nonchalance, wear a single-button oxford under a blazer and keep the cuffs unbuttoned.

What is the rule of thumb to tuck shirts in, if there is any?
Or is it just personal choice?
Of course, T-shirts and polos would be a little weird to tuck in and dress shirts would be exactly the opposite.
But say, casual shirts or half sleeve summer shirts?
Also, would you tuck in just to show off your awesome, new woven belt?

1)     See #3
2)     See #3
3)     Bingo.
4)     Untuck, provided they don’t come more than five inches past your waistband. And if you do tuck, do so only with a shirt that is nicely fitted. The muffin top look is not a good one. Whatever you do, do it all the way. No front-tucks, please.
5)     Oh, yeah, and congrats on that belt.

I’m attending a wedding this weekend. Since it’s an afternoon wedding, I don’t want to wear a black blazer, so my only alternative is a beige cotton blazer. Normally, I only wear this with jeans, so I have no idea what slacks to pair it with. What color slacks will pair well with that color? I’ve always heard that the blazer should be darker than the slacks, so I’m left clueless in this situation. Thanks.
As a general rule, darker pants don’t tend to look all that great with a lighter jacket (excepting, of course, the white dinner jacket, which looks downright slammin’ with a pair of black tux pants). I’d say you’ve got two options: White, which will look great with that blazer and a gingham shirt (but isn’t all that conducive to a furtive romp in the bushes during the reception), or a mid blue along the lines of what Brad Goreski was wearing when he stopped by our studios a couple weeks back (rope soled Prada wingtips entirely optional).

Any style tips for someone who is a little bit on the heavier side?
It’s true what they say about black being slimming, so Rule No. 1 is to stick with darker colors. The opposite’s true of horizontal stripes, so steer clear of French fisherman’s sweaters. Of course, instead of tailoring your wardrobe to your weight you could always follow the lead of the Karl Lagerfeld, who was inspired by Hedi Slimane’s slim Dior Homme suiting to drop over 90 pounds of excess girth. (And he’s kept it off.) Check Gilt MAN regularly and you’ll find plenty of sharply tailored (and affordable) clothes that just may have the same effect on you.

When you want to make the transition from a more “street wear” look to a more clean cut “Gilt MAN” look, what is the best way to start?
Start from the ground up. Put away that collection of Air Maxes and Dunks in rare colorways (don’t worry, they’ll be an eBay goldmine in 10 years) and trade up to some leather-soled dress shoes. A serious pair of wingtips is a great place to start. Or, if you insist on sticking with sneakers, opt for understated canvas along the lines of Converse Jack Purcells, or a pair from Superga, Clae or Gourmet—all regularly available on Gilt MAN. I called style director Josh Peskowitz, who’s in Paris for the Spring ’12 collections, to see if he had any additional thoughts. Sez Pesko: “Once your footwear has been both toned down and classed up, you’ll need to find a new way to accent your look with some color, whether it’s with your choice in tie, or pocket square, or even jacket.” In other words, the pocket square is the new Air Max ’90.

How do you wear a blazer with jeans, and what kind of blazer do I look to buy?
Follow these five rules and you’ll never go wrong:
1)     White, blue, or gingham shirt, tucked in.
2)     Jeans that fit—slim or straight, not boot cut. Either broken-in or dark denim—your call. The latter is dressier. (White denim is a killer option, too.)
3)     Casual brown leather or canvas belt.
4)     Pocket square, in a color complementary to the shirt. Puff, crown, or fold—your call. If you’re wearing a navy blazer, white with navy piping, folded with the piping exposed, is a can’t-miss option.
5)     Loafers with no socks or wide-welt brown or burgundy wingtips with socks that tie back to the pocket square.

How many wears can you get out of your dress shirt before sending it to a dry-cleaner (for laundering) again?
That naturally depends on how warm it is where you live. And, I suppose, whether you’re wearing your dress shirts in an office or on a construction site. I typically get two wears out of a dress shirt from October through March, one during warmer weather. This summer I’ve been wearing lots of oxfordcloth, which you can easily wash and dry at home. I pull mine out of the dryer after about 15 minutes, while they’re still damp and wrinkle free, and let them hang dry overnight from there. And just to be clear, you should get your shirts laundered, not dry cleaned. It’s better for them (not to mention cheaper).

I am from Washington, DC and will be spending the summer in Beijing working. While there I am looking to get some suits tailored and was wondering what kind of fabric you would recommend. Wool is the obvious choice, but should I consider silk as well?
I can see the appeal of having a silk suit made in the home of all things silk, but I’m having a tough time imagining where you’d actually wear that silk suit back in the States. Lightweight tropical wool is a classier option, but if I were you I’d find the best tailor in town and have him make me a handful of unstructured yet perfectly tailored suits made from cotton and linen.

Any recommendations for combating obvious sweaty pits?
If you mean obvious in a visual way, you could try an undershirt, and avoid poplins. If you mean obvious in an olfactory sense, maybe it’s time to consider showering more.

My question pertains to suit fit. I just purchased two suits from Gilt MAN (size 42R) and have an athletic build but am not overly muscular. When I try on certain suits there is quite a bit of wrinkling on the out-facing side of the upper arm, which I assume is associated with my build (my arms extend outward slightly more than the average male’s). Is this something that a tailor can fix, possibly by tightening up the sleeve at the shoulder? Or is this a simple indication of improper suit fit?
You shouldn’t really be seeing a lot of puckering or wrinkling around the shoulder of a suit, so if you have more of a rounded shoulder, you may want to consider going up a size. Just make sure that you have the jacket taken in in the torso. Hope that helps. Drop me a line if not and we’ll get you sorted out.

Hey, Guys! I am a really short and stalky man—I stand at about 5’3″ on a good day. Finding a good shirt that fits perfectly is rather hard. I find that all the shirts I purchase are too long and I am not a fan of tucking my shirts in because it makes me seem even shorter. Should I buy shirts that I like and get them tailored/shortened? Or does that take away from the original shirt?
Those of us at either end of the height spectrum end up on first name basis with our tailors pretty quickly. And as I always say, it’s easier to remove fabric than it is to add it. You should most definitely buy shirts you like and have them altered to fit. If doing so takes away from the original, that’s only in the best possible sense—by making it fit. Just make sure you go to a tailor who’s adept enough with a sewing machine to replicate the seams and gussets at the bottom of your shirt.

Where can I purchase an American flag leather vest?
I promise to tell you where but first you need to tell me why.

We can’t do this without real questions from real guys like you. Send your latest style quandary to [email protected] and we’ll do our best to cook up a solution, either via email or published on the site.

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  1. Rene says:

    I just sent a lenghty email regarding by clothing conundrum. Love the site, and any advice will be greatly appreciated.

  2. null says:

    I’ve lost nearly 40 pounds during the last year, but I still have a tummy. It is much harder now because I work out often, nonetheless it is noticeable. Sometimes I tuck long polos and don’t look too bad but my nipples definitely show. Should I let them hang loose (the shirts) or wear something entirely different. I don’t usually dress formal. Thanks.

  3. Tyler Thoreson says:

    Got it, thanks. Look for an answer on the site soon.

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