First Date Style Tips

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Here’s a question for you: in general, is it better to be overdressed or underdressed? We actually use to always think overwhelmingly, that it is always better to be overdressed rather than underdressed.

The reasons for this was because we felt you could pare down the dressiness of an outfit more by adding something to an outfit that would be considered “underdressed” to the very real concern of looking like a slob in a room full of well-dressed individuals.

When it comes to dating, obviously, looks aren’t everything. But, it can never hurt to put your best foot forward. You want to show that you care about looking nice, as well as on the daily and not just for the date, hopefully, but without going overboard or seeming like you’re trying too hard to impress. A three-piece tweed suit might not be the best first date attire, unless you run in some very fancy social circles.

A first date is also not a time to experiment. You want to wear what you’re comfortable in because people certainly act different when they’re wearing things that don’t feel like themselves in. I think we’ve all been in that situation at least once in life. So with that said, what’s the best formula and how do you walk that fine line? Here are a few tips:

Keep it simple. Stick to the basics and keep the colors muted and classic – blue, brown, black. For example, a bright red shirt to you might seem like you’re putting some effort in, but to her, it might just appear like you’re trying too hard.

Wear dark jeans/pants. It’s likely your first date is going to be a mildly casual affair – drinks or small plates perhaps? – so trade in the tailored trousers for a pair of dark blue or black jeans or casual pants. Find the right pants that match your style here

Add style in subtly. True style is all about subtlety and there are plenty of ways to achieve this. First, instead of wearing an oxford styled button-down, why not try a chambray shirt? It has some texture, is a little rugged, and it’s a simple way to go above and beyond without going too far. Check out some shirt options over at

Next, add in something tailored like a waistcoat. Only try this if you’ve made a habit of incorporating a waistcoat into your regular style. If not, try a nice sweater, or something closer to your normal style, if not, it’s going to be distracting for you and your date. Find the right sweater for your style here

Boot it up. Women pay attention to a man’s shoes. Every guy wears shoes, but not every guy has a nice pair of chelsea boots. If you don’t already have a pair, get some and see if it gets noticed. They are an essential and versatile shoe to own; you can easily dress them up, or down.

Hopefully, this helps someone get through the anxiety of getting ready for their first date. But whether you’re getting ready for a first date, or just an outing, Tailor Vintage can get you ready for any occasion, feel free to check out our website to see our fall collection -


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