Summer Weddings, Belts, How to Pack and Tucking in Shirts

It’s been a long road: we’ve talked about pretty much everything that could be considered attire of any form for men, really, from bags to shoes to ties and hats. Phew! So we’re ending with four great questions from readers. You guys are the best.

Tucking It In

Q.

I am happy with many of my sartorial choices but if there’s one thing that terrifies me it’s tucking my shirt in. My wardrobe right now mostly works around this: in pleasant weather (when I’m dressing nicely) I generally wear either vaguely hip polo shirts or short-sleeve button shirts that look decent (if slightly saucy) with the tails untucked; in the winter I have an array of nice sweaters; for in between I have some lighter-weight pullover shirts. But sometimes I feel that a shirt with a collar that buttons in front (I guess this is a “dress shirt?” thanks to you I know now that “button-down shirt” is the wrong generic term for this, though some of them that I own are button-downs) is called for, and furthermore looking at myself with the tails out makes me look like an embarrassing man-child.

BUT! Is there anyway to tuck in one of these shirts and not look like a tool? I haven’t figured it out. I am relatively tall and slim (6–1, 34 length pant, waist somewhere between 32 and 34, depending on the brand and/or my current fitness level) BUT like many dudes who like fatty foods and don’t work obsessively on their ab crunches, I have a bit of a paunch above the waist — I wouldn’t call it a “gut” per se but it definitely sticks out a bit. This seems to only be accentuated by the way shirts poof out around the waist when you tuck them in. Is there some non-poofy way to do this that I’m just not getting? How much of your shirt tails are you supposed to stuff into your pants?

Anyway, this is turning into more a plea for help for my manorexia than an actual request for fashion advice, but I am still interested in your take. Alternately, maybe non-tucked-in button shirts aren’t the signifier of immaturity that I imagine? I just got a couple J Crew fitted tailored fit dress shirts (sale at the outlets!) and got them in a medium instead of my usual large and they look a little snappier untucked, I think. (Of course, with them I worry whether their pastel hues make me look like a monstrous superpreppie, but that’s a story for another day.) Thanks for any advice you might offer!

A.

I’m a little worried about your manorexia, not gonna lie!

So, this is a matter of taste. Loose shirttails can look sloppy or charming, gross or cute.

Basically, if a shirt hangs down in front of the fly of your pants, it’s a disaster. Because you’ll look all weird and bumpy and stuff, usually. An untucked shirt that stops a couple of inches below the belt can work; but I also find that actually often untucked shirts accentuate a gut. (Also: ties help you feel less chunky!)

I like a square-cut shirt tail for untucked shirts. That way it’s not all weird and schloopy. (Not a word.)

You’ve made the most important move already in dress shirts: SHIRTS THAT FIT. Yeah, why were you buying large shirts? This is a thing dudes do all the time and it’s annoying! It’s like all those ladies who are running around with the wrong bra size in those stories we read every six months in some magazine. Can you button the top button? Do the cuffs land properly at the top of your hands? CONGRATS, YOUR SHIRT FITS. No need to go bigger!

As for the rest of it? You just gotta feel right. Do you feel like your shirt is doing something dumb? Then you’re probably wearing it wrong.

And here is how you tuck in a shirt.

1. Put on your shirt, button it up, put on a tie if you’re doing such, etc.

2. Unbuckle, unbutton, unzip and pull your pants down to your knees. (Heyyyyyy!)

3. Pull your shirt down tight over your underwear.

4. Pull your pants back up, with the shirt underneath the pants. (I KNOW RIGHT?)

5. Zip, button, buckle, etc.

RIGHT?

This sounds obvious? But yeah, don’t stuff your shirt into your pants, it goes wrong. And if you sort of have to fold it about in the back? Your shirts are too big. (Go to Valentino!)

Summer Weddings

Q.

I need some advice.

I have a dark gray/black suit from a couple years ago. I don’t think that really goes out of style (does it? AHHHH being a semi-schlubby straight man is SO TOUGH sometimes). Have any color suggestions for a shirt/tie if I’m going to an afternoon wedding, night reception with a preppy crowd.

Then, probably the bigger issue: I have a dark gray sports coat. I don’t really have a lot of money, so I’d like to be able to use it, but, it being fairly dark and all, what can I do to make it fit the season/current style trends better? Color or fabric suggestions for shirt/pants, even just a general place to start would be greatly appreciated as I’m a bit overwhelmed.

A.

Don’t be overwhelmed! It’s going to be okay. But… an AFTERNOON WEDDING in SUMMER???? Yes, your dark gray/black suit certainly does go out of style.

This is what people are going to be wearing (DEPENDING on the variety of dress that’s specified on the invitation):

But you never know! Here’s what you do: you should also call up some bros that you know who are going and ask what they are wearing. Boys are scared to talk to boys in this way! Make it funny. I mean, it’s easy to say, “Uh, hey, what the heck do I wear to the wedding of Mikey and that harlot, am I right?” (I’m kidding, Mikey’s fiancé, we all know he’s the harlot.)

For a wedding, I really feel like a suit is in order, unless the invite says like “come as a carnie” or “super casual by the lake,” although you can wear a blue blazer with tan pants? Or vice versa? But… it’s a wedding. So think cotton. (When you’re older, you’ll go linen.) Preppy. Joyous. GO TO J PRESS OR BROOKS BROTHERS IMMEDIATELY. J Press is often cheaper. Brooks Brothers runs about $500 in summer suits, which may be more than you want to spend now.

ALSO PRO CHEAP TIP: Tokyo7 in the East Village always has some very nice previously owned suits. Very few summer suits usually, but you never know! (Get them cleaned!)

Going Places

Q.

Sometimes I have to go on business trips and I’ll stay somewhere for several days and I’ll need to wear nice clothes. What’s the best way to travel with blazers? Do I have to carry that dumb bag with me? Is there another way to do it?

A.

Ooh, business trips! The best possible solution is: only bring one blazer and wear it on the plane. Mmm hmm. But if you’ve got multiple meetings or need suits, the garment bag is the only way to roll. Sorry! I know, it’s so weird, it makes you feel like an Olde Time Traveling Salesman or something. I always feel like a grumpy dad.

BONUS THOUGH: HOW TO PACK!

1. Lay out your pants.

2. Lay out your shirts.

3. Tuck in the shirt arms, and fold the shirts in half on a vertical line.

4. Lay the folded shirts across the pants, forming a cross.

5. Fold the pants over the shirts.

6. Fold the shirts over the pants.

7. Slide this square of clothing into a carry-on bag!

BLAMMO. DID I JUST RUIN YOUR MIND??? (To be fair, my life changed when someone showed me this!)

Beltless Nation

Q.

When is it okay to not wear a belt?

A.

• Going out for coffee before showers.

• In gym shorts or other pants without belt loops, including swimsuits and beach causal wear.

• When you are wearing suspenders, obvs, Clarence Darrow!

• When you slept over at someone’s house and they stole your belt and you had to run for your life.

• When you get arrested and they take away your belt. Which they do! So don’t get arrested!

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