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When it comes to dating, men might be more limited in their wardrobe choices than women. While women can wear anything from a dress to jeans and a t-shirt, men have to stick to certain guidelines when it comes to what they wear on a date.

Lucky for you, we’ve compiled the definitive guide of what men should wear on their next date. Whether you’re planning on taking her out for dinner or going for drinks at your local pub, here are the top 10 pieces every man should own before going on a first date:

  1. A quality blazer
  2. Dress pants
  3. A nice button-down shirt
  4. A pair of quality jeans (and boots)
  5. A pair of khakis or chinos (with a great belt)
  6. A leather jacket (in case it gets cold)
  7. A cool pair of sneakers (like Converse Chuck Taylors)

Clothes To Wear On a Date Guys

Stitch Fix men's outfit laydown featuring blue denim, grey t-shirt, plaid flannel button-up, navy puffer jacket and brown chukkas.

The hardest part is over. You asked out your crush, your crush said yes. Keep the momentum going in a first-date look that exudes casual confidence. If you’ve got a laid-back style, the easiest way to take that look to date night is to step it up. More buttoned-up in your day-to-day? Keep your look polished with dressed-down options in tailored cuts.

Here’s how to dress for a casual date.

DO DARK DENIM

A casual date calls for denim. If you told your date casual, they will most likely be in jeans or a casual dress, so it’s important you stick to the dress code (translation: do not wear a suit). Instead of your relaxed fit or light-wash weekend denim, opt for a dark-wash straight-leg jean. It’s universally flattering and will work with a variety of shirts—plus, the darker wash will lengthen your legs, making you appear taller. Be sure to add a leather belt to your jeans if your shirt will be tucked.

Stitch Fix Men’s grey wool peacoat, red and blue plaid flannel shirt and brown slim-fit jeans hanging on a rack with grey chukkas on a white podium.

LAYER WITH STYLE AND PURPOSE IN MIND

Use the cooler fall weather to add depth to your date night look with a layering piece. A sporty but elevated bomber jacket, a casual ¼ zip sweater or a classic sport coat gives you a polished, dimensional look without too much fuss.

Stitch Fix Men’s outfit laydown featuring multi-colored button-up shirt, brown colored skinny jeans and grey oxford shoes.

DATES CALL FOR A COLLAR

A collared shirt is almost always a must for a first date. Unless the two of you are off on a serious sporting adventure, wear a button-up shirt or polo. For a cozy dinner, choose a button-up shirt in a classic print, like windowpane or gingham. Headed to an outdoor concert or a leisurely dinner al fresco? Try a conversational print with a touch of seasonality.

OPT FOR SHARPER SHOES

When in doubt, a dressier shoe is the best option. While oxfords are best saved for suits and suit separates, a Chelsea boot or a derby shoe, for example, will work with dark-wash denim or chinos (if you insist). A canvas sneaker is acceptable for a more laid-back date, but don’t pull out your old, tattered sneakers. A clean, like-new shoe shows you care and took time to prepare for the date.

KEEP ACCESSORIES TO A MINIMUM

Keep your jewelry to a minimum on first dates; stick to a classic watch or cuff. Simple is better when it comes to first impressions. Their focus should be on you, not your necklace or class ring.

PRESENT YOUR BEST SELF

Finally, here are a few first date dos (though we know you’ve got this):

  • Be prompt. Picking them up at 7? Be there at 7. If you’re meeting somewhere, get there 5 minutes early so she will see you when she arrives.
  • Have questions ready. This shows you’re interested in getting to know them. Don’t ask them all at once. Let the conversation evolve.
  • Put your cell phone away. Keep it out of sight to eliminate the temptation to check it. If you must have your cell phone out, set it face down on the table.
  • Have a plan. Don’t pick them up and say “what should we do?” Choose your destination beforehand—then have a couple options ready for later in the evening if all is going well (like after-dinner drinks at a jazz bar or ice cream and a walk).

Above all else, be yourself. Ready to have those go-to date night looks in your wardrobe? Take your style quiz, schedule a Fix and have five curated pieces arrive right to your doorstep. Give everything a try in the comfort of your own home. Keep what you like and send back the rest. Shipping and returns are always free, it’s that simple.

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