How to Look Like a Boss on Date Night

By: Ana Schuler, Savile Row Society

“An image is worth a thousand words.” Appearances are not the end-all be-all, but they do motivate us to feel and think a certain way. When you go on a date, the clothes you wear could very well set the tone for the rest of the evening. You’ve got to walk in looking sharp and confident like the bad ass you are – it’s the first step to having a successful night.

At Savile Society Row, we’d love to help shape your first impression. Of course, your personality comes into play, but we can’t help you too much there (we’ll leave that to the expert matchmakers at Three Day Rule). 🙂 What we can do, however, is make sure that your look adds to the date. Here is how to create a dashing head-to-toe look for your next date night — a look that is sure to make the difference.

It starts with the shirt. Button downs are always a great way to go – most of you already know this. Where guys tend to lose points is with style and fit. Often times, a shirt ends up being a bit big in some areas, and a tad snug in others. It’s important to have shirts that fit properly. You don’t want your date to see you as a project needing to be fixed. However, having a shirt tailored to your body requires a lot of time and money.  Our exclusive men’s shopping platform has a quick fix. We offer a great line of shirts with a superior fit. It’s the next best thing to all-things-tailored.  This blue fine stripe ready-to-wear dress shirt (shown here) is a great start to building a look of casual elegance.

Screenshot 2014-07-18 11.04.43Pair it with a blazer. This shirt pairs well with a navy blue blazer. Try the Southern Proper Navy Blazer, made from Hope Sack wool (shown here). The detailing here is phenomenal. Inside the jacket there are three pockets. One, of course, is for your wallet, maybe a pen, or any loose papers you might need. The other two pockets are a bit more daring and fun, as they are specifically equipped to carry a flask and cigars. The lining of the jacket is made from a beautiful green gingham-patterned fabric that is then tied into the outside on the jacket where there is a hint of green under the collar. These small additions are what really make this blazer stand out among the masses, and in turn, will help you do the same.

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You really can’t go wrong with a pair of khaki’s. Every man should have one or two pairs in his closet. If you don’t already have a pair you, must go out and get it ASAP. They provide you with a large amount of possible combinations in casual or formal occasions.




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A quality shoe is so necessary. Although they’re not in the direct line of sight, shoes really do make or break a look. Here, you have the ability to jazz it up a bit – make a statement by adding a personal touch. Your date will notice the quality of your shoes, and she will certainly appreciate the fact that they aren’t tennis shoes.  A suggestion? Allen Edmonds. Every pair of Allen Edmond shoes is hand made in America with the finest materials around. By getting these shoes, you’re not only helping the economy and supporting American factories, but also sporting art on your feet. The Grayson Cordovan Loafers are a perfect match for any look, and are beyond comfortable.

Screenshot 2014-07-18 11.08.27Now you’ve built a platform to work with. The essentials are done and out of the way but your look is not complete just yet – it’s time to tie it all together. Details matter. A noteworthy watch, pair of socks, and wallet in good condition set you apart. It all adds up in the end.  A nice watch is a good, easy way to add a touch of class. Daniel Wellington’s Classic Cardiff watch is a thin, elegant, timeless watch, and one that will work for any and all occasions.



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Don’t leave the house without a belt. A belt is an essential part of a complete look. By matching the color of your shoes to the color of your belt, you are pulling the whole look together. The coordination of colors is appealing to the eye and makes you look put together. We recommend slipping on a Rafferty belt by Trafalgar.



Screenshot 2014-07-18 11.10.48You must have a well-kept wallet. If you end up paying for the check, you don’t want to pull out a ratty old wallet. I know what you’re thinking. “A wallet’s a wallet.” No, no. You are a professional, so you should have a wallet to match that. The Moore and Giles Bi-Fold is the way to go. This wonderfully slim wallet comes with six card pockets and two slip pockets for your money.



Screenshot 2014-07-18 11.11.47Those are our SRS date tips for now! All clothing suggestions and more can be found here, where you can get your own personal stylist for free. The site is currently waitlist only due to high demand for our stylists, but if you sign up using the Three Day Rule special referral code (, you can skip the line and get paired with a stylist for free today!

 Now, go out there and wow your next date!

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