WHAT ESSENTIAL GEAR DO I NEED?

The 35mm is a great lens(I have 5 lenses and this one is my favorite). Regarding flash the Yongnuo YN 560 III that you can get on amazon (here) for about $70 is a great flash. I have it and I can say that its great.
 
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Okay, many thoughts...

1. If you're going to be shooting mostly outdoors, then it helps to get a 5-in-1 reflector. First, the reflector can bounce around light and reduce some of the extremes. Second, a 5-in-1 will also have a scrim that will soften the light and produce a better portrait. And with that reflector, you'll need an assistant OR a good stand and clamp and a sandbag/water jug b/c the big reflector is a sail that catches wind.

2. I love the Nikon 35mm f1.8. Great little lens, light, reliable. But unless you're going to shoot boudoir or some very stylized portraits, you probably don't need to go to f1.8 (that would put eyes, eyebrows, nose and maybe the ears in focus and the rest would start to blur). Also, you get chromatic aberration with this lens when shooting into light at f1.8 or f2.0. Doesn't mean it's a bad lens--it's a terrific bargain. And, I understand that having two kit lens, you want something that will give you a wide open aperture. But if you buy it, do so with full knowledge. For shooting outdoor portraits, unless you're shooting in very dark space, I don't think this is a particularly valuable lens.

3. I think the idea of getting two Young Nuo speed lights is a good one. Use 'em as optical slaves.

4. I'd also consider buying a cheap stand and soft box/umbrella combo. I say "cheap" b/c you don't know how to use one and if you're going to be shooting outdoors (and thus on the road) your equipment will take a beating. So if you invested $200 on that setup, you'd probably still end up having to replace it in a year b/c it got rained on, dropped in a creek, stepped on, stolen, had coffee spilled on it in the car, got ripped when you were rushing to put stuff away as a storm approached, or got blown by a stiff wind in to the rocks.

5. Start to develop a list of "go to" locations that are perfect for a bunch of portraits. Engagement portrait. Graduating senior. Christening. Family reunion. Musical group. Athlete. Performer/actor/singer. Have a bunch of locations you've identified where it's not going to get you a ticket to set up for a 30 minute shoot. Having one stop for everything just won't work for a serious portrait shooter.

6. Although you said you're going to shoot outdoors, you're going to find that there are just too many instances where someone wants to pose and...it's raining...or storming....or a MUA is involved. Or multiple clothes/wardrobe changes. So if you seriously go into portrait-land for work, you're going to end up doing a lot of work indoors. And that means you'll need some backdrops. Keep your eyes open for theatrical scenery/backdrops (like a ripped stage curtain or cloth) that is discounted. Or colored sheets at the Salvation Army store. And some clamps. Or make a stand out of a lot of PVC. And a good seat (for instance, I used a drummer's seat for the longest time for my portraits work). And old chair with chipped paint and "character" is often times a useful seating and prop tool for portraits. And start to acquire useful props for portraits (since amateur models don't know what to do with their hands...and a prop gives them something to hold.....and a prop can set the tone for a photo). Here are some example of cheap but useful props: a champagne flute, a good artificial rose, a bible, a pair of reading glasses, a pair of sunglasses, a cigar, an expensive pen like a Mont Blanc (that doesn't write), a cloth apron, a long-neck beer bottle or a glass coke bottle, a silver/pewter ornate hand mirror, a baseball or football, a putter or golf ball. Obviously, not all props work with each person. But depending upon the nature of the shoot, the location, and their background one of these props is often a nice touch to a portrait or even a good aid (for instance, I often use a pair of sunglasses for women as an impromptu hair band when shooting outdoors with sudden gusts of wind).

So what lens do you recommend? I was looking at this one cause its so cheap. But I can spend a little more maybe $300? I'd love a 50mm or 85mm, but they are like $500.
And yes I already have the 5 in 1. I have the big one too :) It has really been good.

First, as to the lens question: since you have two kit lens and you aren't talking about shooting indoors in dim light, and you don't have the money to spend on what you really need/fits your needs...than don't buy a new lens. Live with what you've got.

Take that money and spend it on education. Or spend it on a good, veteran model or two (for editorial, glamour work, you could get a good local pro for $100 for 2-3 hours). She'll help you with posing. You'll build up your portrait portfolio with a range of different settings and looks. And then do a ton of TF stuff with students at a local college (they pose for you, they get stuff for their portfolio).

Before you really want to go it as a business, you've got a bunch of things to do that have almost nothing to do with photography (business plan, insurance, marketing, identifying a niche, etc.). So get the photography piece down first.
 
First, as to the lens question: since you have two kit lens and you aren't talking about shooting indoors in dim light, and you don't have the money to spend on what you really need/fits your needs...than don't buy a new lens. Live with what you've got.

So what is a good lens recommendation for outdoor shoots?
 
Nikon 17-55 f/2.8 AF-S DX is nice if you have $1,000 and a DX Nikon body. Sigma 17-50mm f/2.8 is actually HIGHLY regarded by many pros, and is way less costly. 24-120mm f/4 VR is okay. 24-85mm VR-=G, the NEW model, is pretty good,available at good prices, and is AF-S and has VR, silent wave focusing,and shoots good video too. The 50/1.8 AF-S G series is a great lens for $196. No zoom though. The "OLD" 28-105mm AF-D is pretty good, but requires a camera with an in-body focus motor.

There are A LOT of lenses today. The Sigma 50-150mm OS is an amazingly sharp f/2.8 70-200 equivalent for those with DX bodies.
 
Nikon 17-55 f/2.8 AF-S DX is nice if you have $1,000 and a DX Nikon body. Sigma 17-50mm f/2.8 is actually HIGHLY regarded by many pros, and is way less costly. 24-120mm f/4 VR is okay. 24-85mm VR-=G, the NEW model, is pretty good,available at good prices, and is AF-S and has VR, silent wave focusing,and shoots good video too. The 50/1.8 AF-S G series is a great lens for $196. No zoom though. The "OLD" 28-105mm AF-D is pretty good, but requires a camera with an in-body focus motor.

There are A LOT of lenses today. The Sigma 50-150mm OS is an amazingly sharp f/2.8 70-200 equivalent for those with DX bodies.

You know Derrel, when it comes time for me to put together my Christmas or Birthday "wish-list", I should just check with you for ideas! Great list of options.
 

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