Firstly, my apologies for the delay in video episode 3. I’m still in China meeting with our manufacturers and video sharing here (where youtube, vimeo and numerous other American content-sharing sites are blocked) has made the editing process difficult. If all goes well, it should be up in the next couple days.

Anyway, it’s officially layering season. Finally time to put away those heavy parkas – but not quite time to introduce the lightweight fabrics or brighter colors of full-on Spring.

I try to transition my wardrobe gradually over time – although the sporadic weather can make this difficult at times. This time of year, it’s especially important to check the day’s weather forecast before getting dressed.

More than likely, you’ll want to have a few layers that you can add or remove should the weather (or your itinerary) throw you a curveball throughout the day. The trick is to keep the items trim and interchangeable.

Here, five ways to pile on the layers without looking all bulked-up like the Michelan man.

1. Big Vest, Little Vest

A down vest over a hefty blazer (or in this case, a suit jacket) is a look that guys seem to be getting more and more comfortable with. I’ve been doing this for years – it’s a great way to dress-down a jacket and make it look sportier.

The key here, as with all of these looks, is that I could easily remove any of these layers and still have well put-together outfit. The pieces aren’t dependent on one another, they simply compliment one another. For example, if it gets warm I can drop the down vest, or the tweed jacket, or both. Or if I need something more conservative for whatever reason, I can loose both vests and have a more traditional “business casual” outfit.

Bonus Tip: Sneak a tie bar under your sweater. 1) Nobody will know, 2) It will keep the tie hanging straight down from the neck, and 3) if you decide to remove the sweater vest you’ll still have a stylish accessory touch.

Bonus Tip II: Make sure to pull the armhole of the vest all the way over the shoulder seam of the jacket, this will “lock” it in place and allow them to sit more naturally together.

Down vest by Penfield (size S). Tweed blazer (part of this 3-piece suit) by Michael Andrews Bespoke (custom made, my own design). Fair isle sweater vest (size M) and jeans (size 34) by Polo Ralph Lauren. Green stripe oxford by Gitman Brothers (size M). Vintage burnt orange knit tie. Leather belt by Banana Republic (size 36). Suede longwings by Bass. Watch by Montblanc. Watch strap by Corvus. Tortoise shades (in hand) by Persol (“649″ 54mm lens). Bracelets from various street vendors.

2. Sporty & Dandy

Try a rugby shirt as a layer. It’s a little more sporty and style-forward than a regular v-neck or cardigan. I’ve been doing this for years too (if you remember, I wore a similar outfit using this same shirt when I was featured on the Today Show in September of 2009, see here)

Bonus Tip: Don’t have a good rugby? Try a long-sleeve polo shirt instead, it gives you the same effect but is much easier to find in solid colors and simple patterns.

Bonus Tip II: It’s a sporty look, so why not leave cuffs unbuttoned. If your rugby/polo doesn’t have cuffs, you can pull the sleeves up a little and expose the shirt’s cuffs.

Blazer by Hugo Boss (part of the suit feature here, and here - size 50). Rugby by Michael Bastian (size 50). Shirt by Michael Andrews Bespoke (custom made). Bow tie by Polo Ralph Lauren. Jeans by JCrew (“484″ size 34). Loafers by Scarpe di Bianco. Bracelets from various street vendors. Watch by Montblanc. White linen pocket square.

3. Double Up

Sometimes it’s too cool for a light jacket, but too warm for a heavy one. Why not layer too light ones together?

I could easily remove either jacket (or both) and still have a smart casual look.

Bonus Tip: To make a neckerchief look more manly and less dandy, unbutton only the top shirt button and push the bandana down so it just peeks out subtly.

Fun Fact: These red denim gloves were the product of my first ever sewing lesson with my mother a few years back. She was my first inspiration to want to be a clothing designer. See her awesome style featured here.

Quilted jacket by Club Monaco (size M). Vintage Levis denim jacket (size 38). Shirt by Steven Alan (size M). Cardigan by Rag&Bone (size M). Chinos by Helmut Lang (size 33). Boots by LL Bean Signature. Neckerchief is old bandana. Red denim gloves I made from scratch with my mother (she did most of the work).

4. Big Vest, Little Vest – Part 2

A down vest can also be worn under a blazer (or suit jacket). I usually layer it this way with a thinner down vest (with smaller “bubbles”) but as I’m showing here, it can work with a more traditional, fuller vest as well.

Bonus Tip: As I’ve mentioned several times before, the trick to wearing checks together is to vary their sizes, as shown here with the gingham shirt and windowpane jacket.

Bonus Tip II: Popping the jacket collar adds a touch of casual, sporty nonchalance (which coincides with the overall vibe of this look).

Bonus Tip III: Burgundy + brown + deep green. Hell yea.

Green windowpane blazer by d’Avenza (size 50). Down vest by GAP (size S). Brown flannel tie, gingham shirt and tweed waistcoat (part of this 3-piece suit) by Michael Andrews Bespoke (custom made, my own designs). Jeans by Polo Ralph Lauren (size 34). Suede chukka boots by John Varvatos. Belt by Banana Republic (size 36). Vintage linen pocket square. Tortoise shades by Persol (“649″ 54mm lens). Watch and strap by Montblanc.

5. The Whole Crew

As you can tell, I like using down vests as layering pieces this time of year. It’s just such an easy way to transform an “office” look to an “everyday” look.

Bonus Tip: The easiest way to pile on layers is to go from lightest on the inside to heaviest on the outside. Most of these looks, with the exception of #4, follow this guideline.

Bonus Tip II: Not all leather lace-up shoes are “dressy”. There are some awesome soft-sole lace-ups on the market for the perfect balance between dress and casual.

Bonus Tip III: Whenever you’re wearing a layer over a tailored jacket, keep the jacket buttoned. This allows the layers to flow better together and keep their positioning as you move about.

Down vest by Land’s End (size S). Jacket by Michael Andrews Bespoke (custom made, my own design). Crewneck fair isle sweater by Club Monaco (size M). Oxford shirt by Thom Browne (size 2). Wool tie by Woolrich. Jeans by APC (new standard size 32). Cashmere blend socks Marcoliani. Suede captoe lace-ups by Surface to Air. Watch by Montblanc.

Thanks, as always, for reading.

Yours in style,

SB

Photography by Alex Crawford.