Dress like a Man…a Gentleman

Women love a well-dressed man, a gentleman. A gentleman is smooth, impeccable manners, polite, intelligent, witty, talented, modest, well dressed, well groomed, and culturally aware. Does that sound like you?

No? Want to cultivate that? Stick with me; I’ve got some ideas to help you accelerate all the way to gentlemen status! OK, let’s assume you have great manners, are exceedingly intelligent, talented etc… but struggle to achieve that sleek and sophisticated, “well dressed” look.

But what does “well dressed” mean? Well, it is most certainly a subjective term and the modern interpretation of style-even in most corporate settings, it is a looser interpretation of old style standards. It can be awfully confusing to some. Learning to dress casual yet distinguished takes a little work but by building a wardrobe that is interchangeable it is relatively easy to do with the right guidance.

First of all, you could be wearing $5000 Hugo Boss suit and if you are un-groomed- you will throw the whole look off. You do not need to go full metro to look good. But please, if you have a beard- GROOM it. Uni-brow, ear or nose hair? Tweeze or have a professional wax or thread them. No one wants to see that.

Get the right haircut, for you face shape- generally speaking the easiest way to look sleek is a short, tidy, modern cut will give the impression that you mean business. Some of you can venture into more artistic interpretations for your hair, but most of you, please, keep it simple.

Let’s take a closer look at your existing closet. Be honest about your life- what do you need day to day? Business? Business casual? Or just some weekend/casual clothes because you wear a uniform all day. Conduct a needs assessment.

I think the most common scenario of the ill-dressed is….you work in a corporate setting and need to dress up every day but only have 2 poorly fitting button ups and 1 pair of dress pants because “you don’t care what you wear to work”. You have a closet full of t shirts and jeans from your University days, that you live in non-work hours. Are you in your 30’s now? Time to grown up and dress like a man. Be brutal and get rid of it. And invest in comfortable modern clothes that you live the majority of your life in.

Generally speaking Toss/Thrift Shop it if  

  • doesn’t fit (and can’t be tailored)
  • has holes in it (aside form distressed jeans bought that way)
  • stains
  • has tags on it and has been in your closet for over a year unworn

Now that you have cleared your plate you are ready to shop! First rule of dressing well- Know thy rules…so you know what rules can be broken. Those of you blessed with a fat wallet, finding great style is relatively easy. For everyone else, we have to work a little harder to find it at more affordable stores. Good style has no price point, but at affordable stores you need to pay particular attention over all look of the piece- the style- and to FIT and FABRIC. Nothing says cheap quite like a poly-blend sweater.

Only buy clothes that are interchangeable….an interchangeable wardrobe is one with fewer specific pieces, but many possible clothing combinations. Look at what’s in your closet and purchase things to bridge the gap between your current wardrobe and your desired wardrobe.

You will need to start with a few building blocks of good style, every man should consider owning for purposes of interchangeability:

  • A dark suit, navy or charcoal. Find the right suit for you and learn to love it. You don’t have to go ultra-tight, European fit but a proper fitting suit looks amazing. Feeling comfortable in a suit is the first step toward feeling comfortable as a gentleman.  If money is no object- Armani and Hugo Boss cuts amazing suits or get a suit custom-made just for you, if you can afford it.
  • Jeans- dark and slim fit is most modern and can be dressed up or down
  • A sport jacket– Tweed/wool for fall/winter and linen/linen blend for spring/summer
  • Five solid or small-patterned light-colored button-down shirts– Here’s where you can express some individual flair in some patterns in shirts. You could wear it with a suit for the most formal business setting imaginable, or you could wear it with jeans. It’ll work for pretty much everything in between, too. Now that’s versatility.
  • Thin knit- solid-colored sweater. Key layering item. Goes with everything.
  • Two pairs (at least) of flat front dress pants. Grey flannel, tan, medium-grey wool, or khaki. A pair of well-fitted chinos or cords is a third option – but these are more casual, so make sure they suit your needs.
  • Two pairs of dress shoes. Walk the walk in the right shoes. When it comes to shoes, splurge on a top-quality pair of wingtips or oxfords Pick your style (brogues, work shoes, dress boots, loafers, saddle shoes, etc.), but have ‘em. This is how you dress up jeans, or dress down nicer outfits. 
  • Accessories- amp up your style. By the BEST quality watch you can afford. Pick up funky colored socks, bold patterned ties (try a bow tie!) and pocket squares. Unique cuff links look great; just try to authentic and congruent to your overall look.

Splurge on quality suits, belts, shoes, pants and watches- save on dress shirt, t-shirts and some pants.

How do you put it all together? Think about a completely neutral, ordinary outfit for a casual man: dark, fitted jeans and a white (or lightly patterned) dress shirt tucked in. But no man’s going to leave the house wearing just those two items. Turns out those choices make a lot of difference. The same jeans and shirt are going to look very different paired with a broad brown belt and brown desert boots than they would with black brogues, a slim black dress belt with a silver buckle, and a silver watch. One outfit is rugged the other is sleek and urban. That’s the power of accent pieces.

You now are on your way to dressing like a gentleman!


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