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Best Casual Date Looks to Make a Great Impression


The weather might be cooling down, but romance is still in the air. Welcome to sweater weather, the best time to take your new sweetheart to a pumpkin patch, a day of apple picking, or for an impromptu wine tasting. Resist the urge to throw on your old college hoodie just because the mercury is dropping. With the fantastic casual date looks below, you can make a great first impression while staying warm and comfy the whole time.

Featured: White Crew Neck Tee

Timeless Cool

You can’t go wrong with a white t-shirt, sneakers, sunglasses, and a sharp jacket. This timeless look brings out your inner James Dean and radiates an air of effortless cool. The key to making it really work, though, is rocking the right men’s basics.

Start with a fresh white tee and pair it with a good pair of dark jeans. Then top your base layer off with the jacket of your choice. If you want a full Dean vibe, go with a classic bomber jacket, ideally red. Otherwise, a leather or denim jacket will work just fine.

Make sure your sunglasses are on point. Wayfarers are a good choice, but wear whatever makes you comfortable, since it’s your self-assuredness that ties it all together. Scuffed up, smeary, or scratched glasses can make you look sloppy, so double-check that your shades are polished and pristine.

Finally, let’s talk shoes. The eternal question of whether to wear socks or not comes down to personal preference and how much walking you’ll be doing. Loafers work well with this look. When searching for the right pair, keep quality in mind. Suede and leather are good choices, and if you’re only investing in one pair, brown is more versatile than black.

Featured: Charcoal Short Sleeve Henley

Monochromatic Style

It can be a little tricky to pull off a single color look. One excellent tip is to use clothes in the same color realm but with different hues or textures. You can also use accessories to add a bit of dynamic visual interest.

Monochromatic looks work best with dark, neutral, or nature-inspired colors. Try this look with lighter, flashier colors and you’ll risk looking like Lloyd Christmas. So, instead, grab a dark short sleeve henley and pair it with a lightweight sweatshirt in the same color, and then have dark jeans complete the look.

Monochromatic looks allow accessories to shine, so incorporate a deep brown belt, loafers, and a statement watch for just a touch of contrast. If you’re going with a navy look, stay away from black shoes. The colors are too close and it could look like you made a mistake. Instead, go with brown.

Featured: Garnet Long Sleeve Henley

Layered With Denim

By contrasting shades of blue, you’re dressing aptly for the weather while still giving the nod to summer. Denim jackets are exceptionally versatile, and they look great with dark long-sleeved tees. When it comes to denim, fit matters. You want the bottom of the jacket to end right at your hips and the cuffs to hit your wrists.

Go for a lighter shade of denim, but avoid any flashy prints or stone washing. It’s a good idea to avoid customizing your denim too. Wear and tear, like patches and buttons, can take this look from chic to childish in half a minute.

Featured: Navy Polo Shirt

Polo and Sweater Combo

A good polo shirt is the perfect way to take any look to the next level. Polos look fantastic on their own or paired with a sweater in the same color family or complementing color. Crew neck and cable-knit sweaters work well with polos and virtually eliminate the need to wear a jacket.

There are a few key things to keep in mind in order to pull this look off. First, make sure that your sweater is intact. Avoid anything with holes, raggedy threads, or a saggy fit. Also, keep in mind that patterns can be your friend or your worst enemy. A well-placed stripe or muted pattern on a sweater can add visual interest to your outfit, but too much detail can overwhelm your aesthetic rather quickly.

There you have it, four tried-and-true casual date looks that will keep you seasonally dressed to impress. Doing well out there starts with dressing well.

— Elizabeth Lavis

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