Men Know What to Wear on First Date - Styled By Sally

For the guys- what to wear on first date to increase your chances of a second!


You’ve made the move, put your heart on your sleeve and asked for that date. The risk paid off and the answer was yes! One hurdle overcome – now to decide what to wear.

You don’t get a second chance to make a first impression so your outfit choice is extremely important. You want to show that you’ve made an effort and you care what your date thinks. Pride in personal appearance is also an indicator of how you feel about yourself and your values. But you also don’t want to be seen as trying too hard, appear overly vain or shallow and superficial. No one wants to think they’ll be kept waiting whilst their partner primps and preens, or worry they’ll hog the bathroom mirror and the walk in wardrobe.

‘Looking good isn’t self-importance; it’s self-respect.’ – Charles Hix

Being over-dressed will make your date feel almost as uncomfortable as under-dressed, and unless the planned meeting involves some kind of activity involving exercise, under no circumstances should sport shoes be worn. Not unless you want your first date to be your last.

Somewhere between a tuxedo and a pair of shorts is the perfect first date outfit regardless of your age, something classic and timeless that can work in just about any location or activity (except maybe hiking or indoor rock climbing).

A well fitted slim leg denim jean, a fitted shirt in a colour that suits your colouring and taste, although it’s hard to go past white unless your date is going to involve spaghetti, a timeless sports jacket and brown leather shoes can take you from a brunch date right through to an elegant dinner in a fancy restaurant.

‘To attain style in dress, you must look perfectly happy and relaxed in your clothes which must appear part of you rather than a wardrobe you have just donned.’ – Hardy Amies

As a men’s stylist in Melbourne, I have seen that this classic outfit works for the teenager going on their first date and will impress your partner just as much as their parents. It speaks of style and confidence, and can take you from casual to more formal events without a hiccup.

These staple items are found in the wardrobes of most men and can be worn in different combinations to get maximum value and wear, but when combined they pack a real punch and set the perfect first impression. As discussed in How to build a capsule wardrobe, investment in classic pieces that will last season after season are just as relevant to men as well as women and you’ll never struggle to find an outfit for the second and third dates either.

Category: Fashion Advice, Mens

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