Summer dates present a unique conundrum for us men. Fall and winter dates are easier to dress for since those seasons traditionally dictate more formal fashion, making the wardrobe more clear cut. The warmth of the summer months inherently conditions us to dress more casually, but how do we dress for a summer date without looking sloppy?
The key here is to put together a nice sportswear ensemble, something that says you want to have fun and feel comfortable, while still looking good and presenting the best image possible for your date. How do you look good without looking like you’re trying too hard? How do you get that debonair summer style without sweating? The forthcoming tips share a common thread: easy-to-wear style that shows your date that you put forth an effort while still retaining a casual cool vibe.
Shirt
Optimally, you should wear a long-sleeve button down shirt made of lightweight cotton or linen – avoid Oxford shirts during the summer months. Solid colors are safe, but you can add some personality with a fine-checked, gingham or striped shirt. Paul Smith also offers some bolder prints for the more daring, but don’t turn the knob to 11.
Nat Nast or Tommy Bahama-style shirts are acceptable for older gents or those in tropical climates, but steer clear of any floral prints or large embroidery. You don’t want to look like a retiree or a World Series of Poker competitor.
A golf shirt is the most casual shirt you should wear on a date, period; save the graphic and ironic tees for “brocations.” “Love Kills Slowly” is not the message you want to project to your date. If you do go the casual golf shirt route, the logo should never be larger than your thumbnail – you’re selling yourself, not a clothing brand.
Stick with solids here. Pinstripes are too formal and can make it look like you just left the office, while bold prints are too casual and draw too much attention for a date situation.
Ensure that your pants are made of a lightweight, breathable fabric so you don’t sweat down there. Summer weight chinos from the J. Crew line are a trustworthy choice, while linen is a bit more distinguished, yet even more comfortable option.
Lightweight jeans can be worn, as well, but make sure that they are nicely hemmed and are a different pair than those in which you do your yard work. Any shade will do so long as the jeans don’t have holes, but really light-colored or dark, raw denim tend to be the most suitable for dates since they stand out from so-called mom jeans.
Leave your little sister’s jeans in her closet so that you leave something to your date’s imagination. Conversely, you should avoid baggy denim or pants with a drastic drape. The key here is to wear a pair of well-tailored pants that let her see your silhouette without putting it all out on the table.
Shorts should only be worn during recreational activities. Pleats. Just no. Not under any circumstance. Ever.
Coat or Not?
A coat is optional, but donning a dapper jacket serves a two-fold purpose. First, a sport coat shows that you put forth effort and wanted to look your very best for the date. Second, should it get chilly later in the evening you can offer your date your coat, a classic act of chivalry.
Wear an unlined, unstructured sport coat for that summery gentleman look that will also allow maximum breath-ability. Seersucker adds a splash of Southern charm, but don’t pair it with a patterned shirt or you will make your date dizzy.
Don’t just take a suit coat off its hanger and throw it on with your summer date outfit. Women can tell that the coat is meant to be worn as part of a suit, making it look like you hurriedly threw the ensemble together from your work wardrobe.
A solid navy blue blazer is a safe choice, just don’t wear one with a crest or shield or people will think that your date picked you up at a prep school.
Women love shoes, but they also love to judge a man by his shoes. If you are going to splurge on any part of your summer date outfit, this is the piece.
A nicely made, leather-soled pair of slip-on dress shoes is the prime choice here. Add a bit of dressy sophistication by wearing bit-loafers or driving shoes.
Traditional lace-up dress shoes are also fine, but may come across as too formal for a summer date, and also make it more difficult to take your shoes off at the end of the night.
Those who live in coastal locations can consider a fresh pair of boat shoes from Sperry but only for more informal settings. Do not wear socks with them. Ever. Thank me later.
At all costs and with no exception, avoid sneakers, flip flops, canvas and Crocs. They have a place; it just isn’t here.
Accessories
Add a pocket square to your sport coat to show some fashion sensibility and dapper style. It sounds silly, but your date will take note of the extra attention you put into looking your best and women love a well-coordinated man.
Leave your man jewelry at home. A classy wrist watch is fine, but the rest should be kept to a minimum so you don’t upstage your date.
Match your belt to your shoes. Solid leather is fine, but leave the studded belts in your “80s night” pile and donate that braided belt to the Goodwill. Grosgrain ribbon belts are also suitable for those who want to give their outfit a nautical/preppy feel.
Skip the tie, unless you are attending a function that specifically requires one in the dress code.