Style Suggestion: How To Dress for A First Date

Editor’s note: Head this way for more menswear style suggestions.

So, you’ve done it — secured a date! Very well-done, indeed. But what to wear? More importantly, what to wear for a spring or summer-specific situation, like a patio date? Or for that matter, a casual indoor date? You certainly want to dress to impress, but unless you’re heading somewhere exceptionally fancy, it’s probably best to stay away from a full-on suit (that’s step number one). Step number two — read up on a versatile style suggestion geared toward both of those situations– but know that the same building blocks (a stylish chambray shirt, slim jeans and crisp chukkas) can be customized to any season, and with some tweaks (adding a blazer or a sweater, for example), you can create at least two different looks based on the weather. That’s what the below style suggestion aims to get done. It goes without saying that you should look a bit more cleaned up than when out on a bar crawl with friends, and you should certainly class it up from casual weekend style — so, if you want an outfit that checks those boxes, read on! If you have questions in the meantime on how to dress for the occasion, head here or here for style in action. Good luck out there, and let me know

The Jacket: Bridge & Burn Hayden Gray Linen Jacket — $188

A straightforward-yet-stylish jacket with subtle detailing, including that printed liner.

A straightforward-yet-stylish jacket with subtle detailing, including that printed liner.

This piece of outerwear has popped up on the blog from time to time (including in this site’s guide to the best spring jackets), as it’s premium and stylish in a subtle way. It’s a classic silhouette with an updated fit and an easily wearable color, and it’s made with some eye-catching details, including the printed jacket liner. It’s not as dressy as a classic blazer, but functions as a solid outer layer should you need it if the night gets breezy. Other than that, it looks just right over a slim chambray shirt with or without a tie on this first date or elsewhere — it’s playing it (somewhat) safe while exuding great style.

The Shirt: Taylor Stitch The Hyde Chambray Shirt — $99.98

A classic chambray shirt never fails, especially one cut a bit dressier.

A classic chambray shirt never fails, especially one with a bit dressier styling.

It seems that in nearly every style situation, a classic chambray shirt just …. works. When it’s the Taylor Stitch Hyde Chambray Shirt, it’s even better. It’s the more modern answer to a blue Oxford, as it incorporates great visual interest thanks to the textured fabric. Plus, it’s a four-season style essential — we’re talking wearing with a shawl-collar cardigan in the winter, and on its own in the warm weather for a first date. The semi-spread collar leans dressier than a button-down collar, but it can still be rocked without a tie (roll up the sleeves when your jacket comes off to heighten that effect). And if you do decide to go dressier? It would look just right with a grey knit tie.

The Denim: Mott and Bow Slim Mercer Light Denim — $108

A lighter shade that's not quite bright white -- perfect for spring and summer.

A lighter shade that’s not quite bright white — perfect for spring and summer.

While classic dark blue denim would certainly work here, there’s something appropriate to warm weather about lightening up the color of your denim. In particular, a light shade of khaki is a unique style swerve that’s still easily wearable. Some can be hesitant about wearing white denim (yours truly included), so khaki is an easier way to switch up your wardrobe for warm weather. The light khaki color makes the chambray shirt and gray jacket stand out a bit more, too. And Mott & Bow’s Slim fit is going to be pretty agreeable to most body types (even if you’re not used to a slimmer-fitting pair of denim).

The Boots: Astorflex Greenflex Dark Khaki Chukka Boots — $145

Chukka boots that hit the right note between dressy and casual.

Chukka boots that hit the right note between dressy and casual.

A reliable, essential pair of suede chukkas is another safe and stylish bet to make, particularly for a first date. In this instance, these suede chukka boots are understated and casual, yet crisp enough to fit right in with that light khaki denim and blue chambray shirt. The color contrasts nicely with the khaki denim, and again, that essential pairing of chukka boots and a chambray shirt is one that works across all seasons. If the date leans a bit dressier, you could always swap in a pair of leather wingtips. Either way, these boots are sustainably made and sourced, so they’d be a worthy footwear choice.

The Socks: American Trench Triangles and Chevrons Socks — $19.50

Not too plain, not too dressy -- just right.

Not too plain, not too dressy — just right.

As has been the theme of this outfit, sticking with subtle, stylish and slightly refined finishing touches is the way to go. Luckily, American Trench knows that’s just what guys need nowadays. The brand’s socks, though pricey, are a Style Guide favorite for their understated style, nice colors and good selection. The print on this pair plays nicely off the color of the shirt and the denim while not getting too far out there. Although one pair is pretty pricey, it’s an investment that’s worth it — they show a touch of personal style without detracting from the rest of the outfit.

The Belt: Arcade Belt Co. The Hudson Belt — $31.98

Leather detailing that contrasts nicely with the navy color.

Leather detailing that contrasts nicely with the navy color.

Everyone should (ideally) have a classic leather belt in their rotation. Here though, the easy pick is a belt that injects a bit of color into the middle of your outfit while also incorporating some spring and summer texture. If, as we always talk about, style is in the details, then this belt certainly fits that principle. It goes with the overall color scheme of the ensemble, and plays nicely off the blue chambray shirt. It’ll allow you to tuck your shirt in without looking like you left behind a part of your outfit, as well. That’s pretty crucial, yeah?

The Watch: Timex 38mm Watch — $138

Yet another timepiece that features tough Red Wing leather in the strap.

Yet another timepiece that features tough Red Wing leather in the strap.

If you are as of yet unacquainted with the rugged, straightforward and affordably priced stylings of some of the timepieces within the Timex collection, I’d update yourself accordingly now. This revamp really picked up with the introduction of the Timex Waterbury line, continued with the Timex x Red Wing collaboration unveiling earlier this year, and rolls right on through with this simple-yet-rugged timepiece sold via Todd Snyder.  This understated 38mm watch also features Red Wing shoe leather in the strap, which means it’s ultra-sturdy, ultra-stylish and definitely fit for a first date.

The Finishing Touch: Byrd Matte Hair Pomade — $22

An easy way to look good -- a bit of matte pomade and some light styling can go a long way.

An easy way to look good — a bit of matte pomade and some light styling can go a long way.

Some of us eschew hair product altogether, and there’s nothing wrong with that. But, it can be nice to spruce up your mane (particularly if it’s humid out) with a little matte finish pomade — that means you won’t get an overly shiny looking hairdo.  And it goes without saying that you shouldn’t overdo it — just enough to achieve a nice, put-together look. We’ll cover off on more summer grooming essentials next week, but make sure you take care of the basics (y’know, brushing your teeth, wearing deodorant, etc.) beforehand, too.

Preparing for (and then, well, going on) a first date can be a bit nervewracking — it’s about making a first impression, but it’s also about compatibility and finding the right fit. I’ll leave the restaurant/bar/activity choice to you, but the above ensemble should work with some mild tweaks across the spring and summer. The adage that you only get one shot to make a first impression is certainly true, particularly when it comes to style on a first date — clothing isn’t everything, to be sure, but if you start things off looking crisp and polished, that can only signal good things ahead (one would hope!). Plus, first dates should be fun, and dressing in some of your favorite style essentials is a great way to approach it with that mind set. Questions? Comments? Concerns? Head over to The Style Guide Facebook page to keep the discussion going!

Don’t forget to pick up the check,


Buck Mason - Timeless Design. Made in America.


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