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What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. The changing of the seasons is a perfect time to take your significant other out for a night on the town. But, make it special. Put on the best that you have, and go to the restaurant or museum you’ve been putting off. Catch a show or movie after. Decades ago, men and women would put on their best clothes to do what we now see as mundane – dining out, entertainment, etc. Old fashioned? Maybe. But pretty great all the same.

The Suit: Suitsupply Napoli Fit Navy Suit – $399. Or whatever your favorite, well tailored navy suit happens to be. Suitsupply provides half canvas, nice fabric (Italian Wool on this suit), well cut suits for a comparative bargain, especially considering they ship and return for free. Just be warned that their pants can run pretty slim and trim. If you don’t have the time to take an off-the-rack suit to a tailor to dial in the fit, then try Black Lapel. It’ll cost more, but it’s a great option for the broad chested, the big legged, the long and lean… basically anyone who doesn’t fit into the standard suit company “drop” zones most suits are produced in. Full review here of the end to end experience.

The Shirt: TheTieBar Pinpoint Solid Light Blue Non-Iron Dress Shirt – $55. A basic, but done well. Trim fit is not sausage-case tight, but not billowy either. The perfect porridge, if you will. If you’re assembling a foundation to your formal or business casual closet, grabbing a few of these in wheelhouse colors such as this perfect shade of pale light blue is a smart move. That, and the price drops to $46.66 per shirt if you buy three.

The Watch: Christopher Ward C60 Trident Blue Dial – $890 w/ 125LOUPE22 ($1015). All. Blue. Everything. (Alternatively, if that’s just too much blue for you, there’s always the classy black dial version.) This is a dressed up date night, so why a dive watch? Simply, Christopher Ward divers are MONEY when you compare the price-to-spec ratio, especially when looking at some of the other big names in the Swiss watch space. Still pricey for the average Joe, but an absolutely worthy splurge. The benefit of a dive watch here is that it’s dressy enough to look at home with a suit (there’s a reason 007 himself wears an Omega Seamaster), while being able to look just as nice with a polo and jeans. They work with just about any outfit. Full review here of the previous generation. Much of the “guts” are the same, with updated styling on the newer model. Want something more affordable? The Lorier Neptune is an excellent automatic diver for $500 with a Miyota automatic movement and 316L grade stainless steel case and bracelet. Looking to spend less? Try the Orient Ray II for around $140.

The Shoes: Allen Edmonds Park Avenue in Mahogany- $395. We continue the spending spree with the classic Allen Edmonds Park Avenue cap toes. Because, if you’re going to dress up…then dress up. BUT, for a much cheaper alternative, the Dane Cap Toe from Nordstrom is available for just under $100 and have a similar look to the Park Aves. They won’t have the material or build quality, but they’re a quarter of the price!

The Belt: Banana Republic Italian Leather Belt in Mahogany – $60. No need to overthink the belt. A basic, well-made dress belt for a dressed up scenario.

The Tie: The Tie Bar Dotted Tie in Navy/White – $25. With the onslaught of new clothing items each season from The Tie Bar, it can be easy to forget they excel in quality ties for less. It is, after all, what the company was built upon. For something slightly more whimsical but still formal, this “hidden dots” version is a fun take on the dotted blue tie.

The Tie Bar: The Tie Bar Silver Shot – $15. Make use of a tie bar to keep yourself together. It can also be a small way to add a pop of personality to your outfit with something less traditional.

The SocksNordstrom Rib Wool Dress Sock in Navy – $12.50. More Nordstrom, because their house brand excels in formal basics at a reasonable price. Merino wool is perfect for dress socks. Most of you have heard this a zillion times before, but for the newbies: wool is a temperature regulator, and will help keep feet fresh feeling.

The Gift: Flowers from your local farm or florist. Specifically, mums. Mums are great for the fall season, and last much longer than a typical floral bouquet. They’re part house plant, part seasonal decor. If you want to really make them last, gift a pot of mums, rather than just a bouquet.

About the Author: Jason P. spends his days working in the creative marketing department of a big telecom company. He also does a bit of real estate investing on the side. He believes in curating a timeless, classic wardrobe with subtle modern touches for today. He and his wife love hiking with their dog and shopping at local small businesses and antique stores when they travel. Jason is a practitioner of muay thai and traditional boxing, and his favorite drink is a hoppy New England IPA.


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