What fragrances would you pick for me?

From designer fragrances you could check out:

Dior Homme
Chanel Egoiste
Terre d'Hermes

These have a classy chic vibe and can be worn to work or special occasions.

Casual Designers

Gucci Pour Homme II - A tea based scent that wears close to you and smells good. You can wear this anytime/anywhere.
Fahrenheit - It's great but not for everyone, worth checking out.
Rive Gauche - This has that barbershop vibe and is a good masculine and its very popular here on basenotes.
Burberry London - Tobacco and leather with a port wine smell. Solid fragrance though longevity not so good.

For a special awesome designer fragrance that gets a lots of love and is one of my favorites then it is:

Guerlains L'Instant Extreme Pour Homme - Cocoa and vanille combo that lasts for ages and projects really well. Awesome frag.

For Niche which is where things get expensive:

Creeds Green Irish Tweed - This is a wow fragrance when smelled for the first time.
Creeds Aventus - A smoky pineapple frag with apple and jasmine in the background.
Amouage Jubilation - A very classy scent with top notch ingredients.
Tom Fords Tobacco Vanille - Smells great though it is sweet and strong.

Not in any particular order of preference:

For your semi-formal work environment, Derby by Guerlain, Tiffany for Men, Monsieur de Givenchy or Dia Man by Amouage should all do nicely

For casual outside work situations: Terre d'Hermes, Fahrenheit (vintage juice) by Dior, Giorgio for Men (one spray only on this one as it a major powerhouse) or Havana by Aramis

Explore the Comme Des Garcons range.

Terre D'Hermes might be the answer.

Try:

Aqua Fahrenheit by Christian Dior - This is a considerably toned down version of the original, masterpiece Fahrenheit. No negative connotation is implied or should be taken; rather, this is a distinctive composition, somewhat bright and fresh, with ties to the original.
Initially, one is treated to a blast of sparkling grapefruit, with its sour greenness, tempered by a hint of sweetness from the mandarin. This invigorating, citrus melange is drawn to the heart by a nascent mint. Here, in the heart, the cool spearmint comes into its own with its sweet, green facets, and commingles with violet leaf, with its intense freshness and a hint of cucumber. Basil infuses the refreshing blend with a lively dusting of its lemon-like, savory herb. A very faint undercurrent of petro/gasoline can be sensed. Transitioning to the base, a rather ordinary, woods accord presents, and interplays with a light, almost airy, Haitian vetiver as well as a subtle leather. A placid drydown ensues. This high-quality composition is bright and fresh, and should prove to be very versatile. Having average projection and longevity, this scent will, indeed, shine in the spring, summer and fall.

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Eloge du Traitre by Etat Libre d'Orange - Upon application, one is treated to a whirlwind of pine, with its resinous and camphoraceous character, commingling with the lightly herbaceous and slightly medicinal aspects of artemisia, as well as the somewhat mentholish woodiness of laurel. A hint of musky sweetness wafts in the background. Transitioning to the heart, the diffusive, floral fruitiness of jasmine, along with the singular, leafy greenness of geranium, enhance the balsamic, pine-needle freshness of the opening. A dusting of clove adds its musty and charred-wood aspects. Segueing to the base, an animalic and smoky leather interplays with the sweetly camphoraceous and earthy woodiness of patchouli. A somewhat dark and musty musk flutters about. A comforting drydown ensues. A welcomed addition to one's wardrobe, this manly and outdoorsy composition is well blended and balanced, with average projection and longevity.

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I can tell you some my dh loves to wear and I love him to wear. He has a very nice wardrobe of fragrances but these are some of my favorites.- Luten's Ambre Sultan, Parfum d'Empire's Cuir Ottoman, Montale's Patchouly, Mona di Orio's Vetyver and Sonoma Scent Studio's Incense Pure.

+1 : Terre d'Hermes, Rive Gauche, and Aventus for warm season
+1: Jubilation XXV and Tobacco Vanille for cool season

I am not sure what grampas smelled like (Old spice?), but Rive Gauche is not it.

In addition to the many great suggestions, I was thinking whether you shouldnt rather get some more avantgarde stuff, given the people you interact with. CDG has been suggested already, one would be CDG 2 man, lemony incensy, relatively fresh so it would work both seasons.

The Etat Libre dOrange line would also fit well. Part of the fun there is the imagery associated with the scents, which of course wouldnt show. Eloge du traitre has been already suggested. Perhaps you could also check Tom of Finland, a smooth saffrony lemony leather. Probably more wintery than summery, but again, it is not heavy so it would not be out of place in most of the summer.

For the hottest humid days here in DC I like Chanel Sycomore, a very natural, fresh vetiver with a touch of woods.

cacio

Even though you have tried Versace Man Eau Fraiche, please do not let that stop you from trying Versace Pour Homme. VPH has a very clean crisp sophisticated smell to it and you do not have to worry about it overpowering those around you.

I'd recommend at least trying the original D&G The One, or even The One Gentleman. They are both better options than the sport edition. Also, Chanel Edition Blanche, YSL L'Homme, Bleu D'Chanel, DSquared2 Rocky Mountain Wood, Marc Jacobs for Men... these are all quite nice for classy, but sensual scents among so many others.