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A few thoughts from Mr. Swingularity (and Mrs. Swingularity has always stood and watched in awe at Mr. Swingularity's ablity to shop fearlessly for himself and her). Before reading the suggestions below, please know YMMV and these are IMHO and you should BE YOURSELF, not try to be someone else. 1) Shoes. These are your foundation. No sneakers. No work shoes. Nothing you walk the dog or mow the grass in. They should be leather. On trend slip-ons, chukka's, ankle boots, and the like are a start. 2) Socks. They need to have been purchased sometime in the last 2 years. Don't be afraid of colors. Black shoes, black/grey/navy base socks. Brown shoes brown, tan, earth tone socks. 3) Belt. Should RELATE to the shoe color. Leather. I like wider belts on even dressish pants, as well as jeans, as they don't pinch or allow pant to bunch above or below. 4) Underwear. Bought within last year. Don't be afraid to go with bold colors and patterns. But black is a sure bet. I like the cotton blend with some stretch fabric boxer briefs that are low on fabric volume. A "boy short" cut. Looks flattering when I'm relaxed, and really nice as arousal finds me. 5) Pants. Lots of options here. One non option: PLEATS. Never, never, never on pleats. They add unflattering volume, and contrary to what "less fit/slender" guys think, they DO NOT make you look slimmer. They make you look NOT slimmer. FLAT FRONT PANTS ONLY. Dress jeans can be really great. Casual chic dress slacks that aren't business focused are everywhere today, and look great. Dress flat front Khaki's in non-tan colors are all around and look great. A slack with some pattern that is subtle can be great. I love blacks and shades of grey, but have red, mauve, dark brown, loden, etc. Thin dress cords in Fall look super. And did I say NO CUFFS? No? I am now. NO CUFFS. Buy the pants for your fit now, not what you hope to fit after losing that 10 or 20 that you're about to lose. 6) Shirts: lots of options here. Don't like polos, personally. Sorry guys, but dress polos are for the country club golf outing. "Club" and casual dress shirts are all around. I prefer non button down collars and collar stays. I think they look, in general, more aesthetically "flowy". Another look that is nice is a stretch t-shirt, black, under a long sleeve knit. Adds nice layering, and can hide a few extra lbs. The t-shirt is like a Spanxs effect. 7) If it's jacket weather a nice unstructured blazer, and there are tons of them, is a nice touch to start the night in. Says something about the man that is akin to "I care about my appearance", so I must be a "care about my partner and my lovemaking" kind of guy. The fit is key here, gents. So many guys have a jacket that's a size or more too big, trying to "hide something". It backfires. Get the perfect fit and drape, and you'll look sleeker. I have one blazer I love: it's a leather blazer in black that just smokes the night. Like a dress jacket meets bad boy club hopper. ? Have a nice watch? They speak volumes. Finishing touches: Your feet are self pedicured. Your fingernails are clean, clipped close, and looking good. You are always shower fresh and not heavily fragranced. And your oral hygiene (that means floss and tongue scraper) is impeccable. You'll look good, feel confident, and be the best you can be...and get noticed. What happens when you open your mouth...that's up to you! Well, this is all fairly brief, YMMV, IMHO, and feel free to think "Dude...wtf?!?!" These basic principles have been in place for me since about my mid-to-late 30's, and refined over the years. If the feedback my wife gets about my attire is anything to go on, the ladies notice. I'd be happy to hear any tips or thoughts on the whole "male attire" issue from others. I'm always looking for ideas! Well, it's off to give my wife a minty fresh kiss... Mr. Swingularity