The Button-Down
If a button-down hangs below your hips, Esquire says that tucking the shirt in is a must. Guys, it just looks sharper. Whether you’re wearing it with dark jeans, corduroys, khakis, or dress pants – always, always keep the button-down tucked if you’re in dress pants – make sure to use a belt and tuck the shirt in nice and tight. The last thing you want is an anything-but-modern blousy tuck. If you’re wearing a jacket over a button-down, take GQ‘s advice and keep your shirt tucked in.

For a more casual look, go ahead and keep that button-down untucked – but make sure your proportions are clean. The shirt should hit above your hips, and take care to avoid pants that are too roomy. This look can easily sway toward sloppy.

If you’re adventurous, try the half-tuck. Tuck in half of your shirt, letting the other section fall over to the side of your belt buckle. The front-tuck, with both sections tucked behind the belt buckle (as seen on The Sartorialist), is another variation. This look falls into more casual territory, but it also has a bit of debonair flair (see David Beckham rock it) and shows that you’re comfortable experimenting. Proceed with caution, though, and trust your gut – the partial tuck can easily go wrong.

The Polo
The polo is inherently more casual, so the general rule is to leave it untucked, but there are a few exceptions. Esquire‘s below-the-hip rule also applies here, so if your polo is on the long side, tuck it in. On the golf course, always go with a nice, clean tuck and be sure to wear a belt – your look should be as sharp as your game. Likewise, if you’re working a polo on casual Friday, tuck it in to maintain a more professional vibe.

Looking to push some style boundaries? You can also attempt the front-tuck with a polo, but again, proceed with caution. I would only recommend it with a looser shirt and belted pair of well-fitting jeans. If you’re not feeling 100% confident (and totally nonchalant) about it, this front-tuck is best left alone.

Our Original Penguin Boutique opened Wednesday, May 1, at 11AM ET.

By Chrissy Makkas, Staff Writer

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When it comes to men’s fashion, there are a few things that remain timeless: bow ties (yes, there will always be someone awesome rocking one), dapper loafers, and polo shirts, to name three. But what is it about the polo in particular that seems to translate to all types of style? From athletes to punk rockers to Nantucket-bound prepsters, you can find them all rocking this casually comfy staple, and here’s why:

1. The Collar: Whether popped or laying classically flat, this is possibly the most important part of the polo’s anatomy. Ever since the dawn of time (a little dramatic, but close enough), it’s been debated whether or not this staple should be popped or not – Esquire investigates.

2. Casual yet Dressy: It’s almost as if casual Friday was invented with polos in mind. For those occasions where you’re unsure of the dress code, for first dates, for meeting the parents, for a night out with the guys… the list goes on. And don’t get me started on the layering abilities.

3. Versatility: These toppers can be worn paired with just about any bottom. From jeans to khakis (even shorts can be coupled in here), there’s no limit to your pairing options. As for suit pants? Stick with a buttoned-up number.

4. Golf: As long as business meetings, resorts, and movies like Caddyshack and Happy Gilmore are around, so will this beloved game and its not-so-secret uniform. Most country club dress codes even require you to wear a polo in order to play a round.

5. History: Originating from the sport of polo in the 18oos (only with long sleeves), the polo shirt didn’t take off in the fashion industry until 1926 when Rene Lacoste first donned a short-sleeved version at the U.S. Open Championship.

Refresh your collection in our Tailorbyrd Boutique opening Saturday, January 19, at 11AM ET.

By Abigail Kuzia, Editor

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6AM: Early morning run. Resolutions aren’t so hard to keep when the music (literally) plays to your own beat.

7AM: Choose a room-commanding power suit (just follow GQ’s tips for each body type) and remember to add accessories. Cuff links and accent socks go a long way.

8AM: Grab a cup of coffee and get to the office early to crush it.

9:30AM: Client meetings all morning. Although this is run-of-the-mill, don’t forget to brush up on your meeting skills to keep things running smoothly.

12PM: Conduct a meeting with senior management. Just don’t forget the fundamentals of business.

1PM: Lunch with the guys. Get away from the office for a quick bite, a walk, anything to help you clear your mind for an hour or so. Studies show that leaving your cube helps you think outside the box.

2PM: Take a client call and work on proposals and paperwork. This time also usually includes tweeting. That’s right – businessmen tweet, too.

6PM: Happy hour with coworkers and dinner on the town. Swap your office attire for a more casual button-down before heading out (yes, this requires planning ahead). Go for something with a fun, printed cuff to stand out from the sea of suits.

Our Workplace Warriors: Men’s Suiting Essentials Boutique opens Saturday, January 12, at 11AM ET.

By Abigail Kuzia, Editor

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Whether you’re single or in a relationship, dating around the holidays is unlike any other time of year. Here are some foolproof looks for any rendezvous you might have planned during this festive season.

The Nutcracker Ballet
Even if you’re not the biggest fan of ballet, seeing The Nutcracker with someone can be a really romantic and enjoyable evening. Especially when followed by champagne at intermission and a fancy dinner. Keep your look semiformal with a blazer, slacks or dark denim, a dress shirt, and maybe even a tie (possibly a red tartan one).

Blind Date with Your Mother’s Colleague’s Cousin
It’s the season for merriment and yes, blind dates. Often set up by well-meaning family members, these potentially awkward meetings call for an outfit that’s date-appropriate, but isn’t trying too hard. Try straight-leg denim, a button-front shirt, and a neutral-hued V-neck sweater to make a dapper impression.

The Holiday Party
The key is to not show up wearing a hand-knit holiday number a la Colin Firth in Bridget Jones’ Diary (bonus points if you got that reference). Keep the festive revelry subtle with a couple of nice touches, like an appropriately colored tie or sweater. The rest of your ensemble should be simple and neutral, e.g. dark pants and a white dress shirt.

Ice Skating
Whether you’re a pro or not, ice skating is a perfect date for the holiday season. It’s active, fun, and you get to treat yourself to some delicious hot chocolate afterward. Bundle up to stay warm (without looking like a snowman) with straight-leg denim, a cozy plaid button-front shirt, chunky sweater, and warm wool socks.

By Christine Mitchell, Staff Writer

What are your date-dressing tips? Share them in the comments below or tweet us at @ruelala.

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