“Any tips for what to wear on a casual first date? I want to look sharp, but, y’know, not like I’m trying too hard.” —Damon
So, you’ve got a first date on the cal. You’ve lined up a few conversation starters, and now it’s time to map out a look that exudes casual confidence. When it comes to the best first-date looks, simplicity is key. They should be stylish but not showy, comfortable but not sloppy, put-together but not stuffy. If you’ve already got laid-back style, the easiest way to take that look into date night is to step it up with a few elevated touches. Maybe you swap in your everyday jeans for crisp chinos, or the sneakers you’ve worn everyday for the last 3 years for a pair of crisp white kicks. More buttoned up in your day-to-day? Lean into your polished look with dressed-down options that still have a tailored feel (you’re not conducting business, after all).
Whatever your vibe, it’s about showing off your true sense of style by putting in some effort for the occasion. Below, we’re sharing the 4 low-key date staples every guy needs in their wardrobe.
If there’s one thing a casual date calls for (aside from your charming personality), it’s dark-wash denim. If you told your date that the vibe of your outing will be casual, they’ll most likely show up in jeans or something laid-back, so it’s important you stick to the dress code yourself. There is such a thing as being overdressed, so don’t go showing up in a suit—no matter how sharp you look!
Instead of your relaxed fit or light-wash weekend denim, opt for a dark-wash straight-leg jean for the special occasion. A darker wash lends extra polish to your look, while a straight-leg fit is universally flattering and goes with a variety of shirts. Pop on a classic sweater, a polo or even a chambray button-up (just make sure the wash is a full shade lighter or darker than your pants). Whatever makes you feel your best is always the right move.
A collared shirt is almost always a must for a first, or even 20th, date. Unless the two of you are off on a serious sporting adventure (pickleball, anyone?), a button-up shirt or polo are both comfortable options with a little extra polish to show you’ve put some thought into your look. For a romantic dinner, pull out all the stops with a crisp oxford in a classic print, like windowpane or gingham. Headed to an outdoor concert or a casual dinner al fresco? Try a conversation-starting print that reflects your sense of style. For a cold-weather meetup, opt for a cozy flannel that’ll bring out your warm and fuzzy side. Skip the pre-date pile of rejected shirt-pant combos and reach for chinos or dark denim—they’re the perfect match to any collared shirt style.
Cold weather (or even a cool summer evening) is a great excuse to use a layering piece to add some depth to your date-night look. Stylish outerwear has the power to take your look from “this guy knows how to put on a shirt and jeans” to “this guy knows how to put himself together” (otherwise known as *the* goal when making a first impression).
When it comes to choosing the perfect jacket, keep the activity, venue and weather in mind. A sporty-yet-elevated bomber jacket is a solid option for a more casual outing, and looks great over everything from tees to flannels. If you’re looking to give off a more rugged vibe, a utility jacket plays well over a simple crewneck sweater. Heading out on a later-in-the-game date with a fancy agenda? In that case, a tailored sport coat will serve you well—and earn style points from your date.
When in doubt, our Stylists say to go dressier with your shoe choice. While oxfords are best saved for suits and tailored separates, a Chelsea boot or sleek leather sneaker, for example, will work with your typical date-night fare (read: denim, chinos or even corduroys). While a canvas or athletic sneaker is OK for an outdoorsy meetup that calls for a very casual date outfit, don’t just pull out your old, tattered sneakers. A clean, like-new shoe shows you took some time and care to prepare your ensemble. Now that your footwear game is in check, you’re date-night ready from head to toe.
Get styled by Stitch Fix for date night
Wondering what to wear on a date? Let our Stylists help get your wardrobe rendezvous ready. Take your style quiz, schedule a Fix and get ready to receive an array of men’s date night outfits that fit your unique taste. Try on your new outfits in the comfort of your own home. Pay for what you love, and send back the rest. Shipping and returns are always free, and there’s no subscription required. You go make a great first impression, and we’ll make sure you feel confident doing it.