No one ever said feeling out a dress code was easy – especially when it comes to the suit versus the jacket (and, more specifically, the sport coat versus the blazer). One thing is for certain, though: whichever form of suiting a guy chooses to don, there’s no way he’s not going to look pretty darn good in it.

The Sport Coat
Its origins rooted in hunting, this look’s most casual of the three. Wear it to dates and to brunches in the city. Best part? It counts as dressy casual at work.

The Suit
A suit will almost always be appropriate at weddings, job interviews, and formal workplaces (in navy), and at funerals (in the requisite black).

The Blazer
A bit more formal than the sport coat, the traditional blazer is navy and usually comes with metal buttons (chalk that up to its roots as a boating club jacket). Chinos and jeans are both fair game with this one. In my personal opinion, it never, EVER hurts for a guy to have a blue blazer handy. Keep one in your office or your car; you never know when you’ll be needing it.

Our Rue Trunk Show: Men’s & Kids’ Suiting Boutique opens Wednesday, October 24 at 3PM ET.

By Sarah Stanley, Staff Writer

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You heard it here first: Style is alive and well in Boston’s clubby, white-shoe financial world, and we’ve met a man who proves it. In a city that some would say “plays it safe” when it comes to fashion, it was refreshing to find someone who isn’t afraid to push the envelope. Here, our favorite financial planner dishes on his style dos and don’ts.

Rue La La: You work in a very conservative town in an uber conservative profession - how do you incorporate some risks into your style?
Andrew: I wear pocket squares that match my ties, I incorporate a ton of pink, and I also wear argyle or colored socks that work with my tie’s color scheme.

Rue La La: What are some of your workday style “rules” - we know you financial types have them!
Andrew: Belt must always match shoes (a no-brainer in my book), suit and tie Tuesday through Thursday, I never wear a blazer with slacks and a tie (always a suit), and my shoes must always be shined. And never, ever square-toe shoes, black suits, button-down collars with a tie. And no jewelry.

Rue La La: What about non-business days? Do you have a weekend uniform?
Andrew: Usually golf attire as I play every weekend (shorts and a polo), sweats when relaxing, jeans, blazer, and shirt at night and loafers with no socks.

Rue La La: Tell us about your signature style elements.
Andrew: Pocket squares, the color pink, and “different” socks. Sean John or Dolce&Gabbana Light Blue for fragrance. And I have three pairs of monogrammed cufflinks, all from Brooks Brothers. One is plain silver with old English script initials, another plain silver with block initials, and lastly and most importantly there is a silver and blue handpainted enamel pair with white block initials - I’d definitely grab those first in a fire.

Rue La La: Do you shop vintage?
Andrew: Yes, I have two vintage blazers from the Garment District - solid tan and tweed. I also have two V-neck Lacoste sweaters (one yellow and one red), and one navy cardigan. Actually reminds me, I should go search for more!

Rue La La: Who are your style icons?
Andrew: Rick Fox, Sean “Puffy” Combs, André 3000, Terrence Howard, and Kanye West.

Rue La La: What’s your dream vacation, and what would you pack for it?
Andrew: St Tropez - because I rarely relax and it seems like such a relaxing place. I would do nothing but hang out and relax! All white. White linen pants, shirts, and bathing suit along with a pair of flip-flops and sunglasses.

Rue La La: What’s something style-related you’ve been coveting for a long time?
Andrew: A tan seersucker suit. A summer essential!

Rue La La: Now it’s time to dish. Embarrassing fashion moment?
Andrew: I wore a shirt a couple months back that I’d had handmade when I first got out of college. I hadn’t noticed the back collar was frayed. A stylish woman in my office pointed it out to me one day, and I threw it away on the spot.

Rue La La: What inspires you to dress up every day?
Andrew: My dad always had his clothes custom made and he always would say, “You never know who you’re going to meet.” Every morning, I approach the day that way - because you never know who you’ll run into.