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For fitting suits in general, if you are "athletically built" i.e. your chest to waist ratio ("drop" in men's fashion parlance) is greater than 6", off the rack suits are usually a no-go.    Made to measure is a good choice.  Your tailor measures your body, you pick the suit cut & details like fabric, linings, belt loops, etc. and they email your specifications to a factory that makes the suit to your desires and ships it to your tailor.  It is cheaper than a true bespoke suit but gives you much more control over what you want and requires the bare minimum of fitting and alteration upon receipt.   Selecting a good tailor whom you can develop a solid relationship with is important.  They can educate you regarding what is appropriate for appearance and fit.  When it comes to belt loops, you may have to have them placed in an irregular pattern due to where you place your holster and accessories on your waist.  If you wear an ankle holster for either gun, IFAK, or TQ, stay away from slacks that have a slim cut at the cuff. 

Dress shirt fit can also be an issue if you are in decent shape.  Be prepared to have them fitted as well.  Depending on personal taste and clientele expectation, french cuffs (the kind that require cuff links) or barrel cuffs (the normal button kind) are different options as well.  If you wear larger watches like a diver's watch you may also want the cuffs to be two different sizes.  Also, your jacket sleeve length is important depending on the amount of cuff you want exposed.  Shirts are also going to wear out faster from rubbing on your gun and other equipment. 

Other things you need to consider is belt, shoe, and leather gear selection.  Shoes that look good but are also comfortable and supportive are hard to come by.  Generally speaking, lace-ups are better in these regards than loafers.  Belts should be custom made and will be costly but are worth the price if done properly.  Consider having your leather gear and belt made by the same person.  Personally I would suggest having at least two if not three complete setups (belt, shoes, and leather gear), one in brown, one in black, and possibly one in cordovan.  By going this route, you can wear the same suit multiple times but with a different tie and accessories to make it look like you are wearing a different outfit.  It will also allow you to tailor your look to your clientele.  For instance, older more traditional clients might expect "the help" to sport the more subdued look of a navy suit with black wingtip shoes and belt while younger more "hip" clients might appreciate the flair of the brown cap toed shoes and belt combo with a navy suit. 

Ties (including tie tacks or bars), pocket squares, and watches also should be matched to client expectations.  Generally speaking, try to mimic what the client wears as far as style unless the client looks like a sack of shit, because there are plenty of guys & gals with money that have zero fashion sense.  A good rule of thumb is if there is any doubt, lean toward a more conservative traditional style of dress.  Think more Brookes Brother and less Armani. 

x/S

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I wore suits almost exclusively for the last five or so years of my career. Before that I wore them for court or big meetings for work, and limited social occasions.  I always bought suits on sale at Jos. A Banks. I never had issue with sporting the belt gear I carried during the fitting process. I considered these a good happy medium: the suits looked good and wore well. Granted, I was a boss by that time and I wasn't jumping fences, running down dark alleys, or hooking and jabbing with bad guys so "wear and tear" meant not spilling coffee on myself or snagging a pocket on a desk drawer. Daily I carried a Glock 22 (then a 23), spare mags, and cuffs on the belt and a 27 in an ankle holster.

I never tried to look like 007 (and with the amount of gear the OP said he needed to carry not sure you could), just be able to carry what I needed and not have it print or look like somebody threw a blue pinstripe poncho liner over a refrigerator. The custom guy thing was out there but living in a high COLA area plus making a mortgage and helping to pay for kid's college just didn't make that possible.

I will echo the usefulness of black, brown, and cordovan (ox blood) belts and shoes and ties that let you mix things up. Very useful and can help you transition from formal business setting to night time semi-formal setting just by changing your leather gear.

Be prepared, if you stay in the gig long enough, to have stuff wear out and replace it. This stuff is not made to weld in. Try to find the happy medium of price you are willing to pay (can afford)/looks good/fits well.

Like a lot of things in life, for example firearms, I wish I had learned about proper men's clothing earlier in my career and had not wasted time and funds on poor choices.  It is much wiser to initially spend more money acquiring quality gear/clothing that will offer many years of good service, than to choose cheaper, poorly made stuff that will rapidly wear-out or go out of style.

I may be wrong but I think it will be tough to hang all that gear under a business suit.  Current “designer” fad is the tight fit jacket that is short and none too professional.  I just dont get that look.  I second the made to measure option.  A lot of smaller mens clothing stores have the option.  Or try O’Connells mail order in  Buffalo.   Great store but pricey

The real trick is to find the real deal tailor.  Not the guy who just does sleeves and pant legs, but the guy who can make your work for you.  Thats how you get the right fit

Late to the party. Speaking as a 25 yr atty  who carries often and  who worked at Macy's in a former life.

Your initial selection is fairly modest in terms of quality/wool content etc relative to many of the previous recommendations.  Some random thoughts.

1. the leather of your 1.25-1.5 inch double thickness purpose designed leather gunbelt when mated to a quality holster  is an excellent start as were the Perry Suspenders if you really are going to have a bat belt. Many off the rack pants' belt loops do not play well with a 1.75 inch wide gunbelt. 

2. The color of your very shined leather shoes should match your belt. I am fond of Allen Edmonds  and and Eccos in the OEM leather soled/rubber soled categories, respectively.

3. A modest suit that fits you well,  pressed well, when worn with an obviously ironed/laundered shirt and quality 100% silk tie can get your over the top. 

4. A simple pocket square makes any suit pop.  

4. Your gear is going to start to wear holes in the liner of your suit jackets fairly quickly. Unless or until you have them "double lined" with a heavier fabric,  the judicious application of a couple of layers of clear packing tape in those spots with extend the liner life almost indefinitely. 

YMMV Greatly. be safe and well.

Writing as someone who was in the corporate world for many years, I suggest:

1. Always go with top flight fabrics like wool. Some new wool blends now have some elastic so  there is some give - may be nice. They weren't available in my suit days. Good wool fabric drapes very nicely.

2. Back in the days when "Today's Man" was in business, they had suits that came with two pairs of pants - that was great. Once in the office, I took off my jacket for the day, so the pants got a lot of wear.  If you go the custom route, look into an extra pair of pants.

3. The same suit and shoes shouldn't be worn every day. Put them in a rotation - they will last longer and you will look better with a slightly different look every day.

4. Make sure the suit fits. I've seen people who have very broad shoulders, buy suits that are wide enough for the shoulders, but they hang straight down, resulting in a body that looks like a refrigerator.

5. Use a mirror - take a look at how you look. So many people out there make you wonder if they owned a mirror and realize how they look.

 

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