Well, it’s everyone’s favorite time of year. Your annoying aunt has been hitting her bottle of wine a little too hard, you’ve squeezed into a sweater that is two sizes too small – that you’ve probably had since high school, and you’re doing your best to fly under the radar.

Yes, I’m sure you’ve guessed it by now; I am talking about the dreaded Holiday season. It’s always full of family holiday parties that you attend with more than your fair share of apprehension, and the work dinners that you feel down right obligated to attend. All the while you’re turning over and over again in your head, “What do I wear to these things?”

OK, maybe you’re not. But just in case that’s okay because I’m here to help. Just follow my 5 foolproof musts for standing out (in all the right ways) this year.

I’m going to begin by laying out the basics for everyone, then dive in a little deeper and showcase some of my picks to ensure you make the most of it. I want you to remember these three things this Holiday season above all else.

• First: Fit over price. If it’s going to fit correctly, it’s going to cost a little more than you’re used to paying.
• Second: Splurge. Reward yourself with at least one high-end item. I’ll let you use your best judgment here – but be smart about it.
• Third: Mix it up. Mixing a great fitting, high-end item can completely revamp an outfit – maybe even a large part of your closet.

5 Must Haves

jacket

1. Leather Jacket: A well-made, great fitting one. I suggest a cropped racer or a bomber jacket. This is one item I would definitely splurge on. A good leather jacket can easily take the place of a blazer and help keep you from blending in with the crowd. BUY HERE

MS00371_OATMEAL

2. Knitted Sweater: The chunkier the better. Make sure to buy it snug so you don’t look like you’re wearing something your mother bought, but keep it loose enough that you don’t look poured into it. This is what people are going to see once you’ve taken your jacket off, so make sure to pick the right color. Mustard, wine, and cream will be your best bets. A cable knit sweater like this from Brooks Brothers. BUY HERE

shirt

3. Patterned Dress Shirt: Here’s your chance to throw in something you already own, or opt for a lower price pointed item. This guy isn’t going to see a lot of the limelight, so the fabric and label aren’t as important as the standout pattern or print that you’re choosing to don. Yes, the whole button up under a sweater is getting a bit worn out by now, so make it fun. Think outside the box with Levi’s Graves Check-Pattern Button Down. BUY HERE

jeans

4. Jeans: Dark washed jeans, like Big Star’s Division Straight Leg Jeans, are your best bet – they’re dressier than their lighter counterparts, and they don’t scream “denim” as loudly as the others. This is where my “fit over price” rule will come into place- take some time picking out the right fit, and don’t stress over the price tag. If you’re buying a great pair of jeans, they’re going to last you a few years. Think of it like you’re investing in your future, because really you are. No one wants to see your family jewels, or the waistband of your boxers. Keep it clean and simple, fellas. Thick stitches and all that business on the back pocket? It’s best left for our overly tanned and muscled friends on the Jersey Shore. BUY HERE

boots

5. Chukka Boots: A colleague of mine has been in the shoe business for close to 50 years now, and he swears by these guys. The Air Colton Winter Chukka Boots from Cole Haan is the perfect height for wearing with jeans, and the cap toe keeps it dressy enough without being tied down to the generic dress shoes that have been around since before we were even a thought in the back of our dad’s head. Another budget friendly option would be the Real-Deal from Kenneth Cole Reaction. BUY HERE

Now that I’ve laid everything out for you, I hope your mind is a little more at rest. Maybe you’ll even enjoy yourself now that all that stress has been lifted from your shoulders? Hopefully I’ve endowed you with a double shot of self-confidence and a renewed sense of your own unique personality that can show through your impeccable duds this Holiday Season.