Menswear has become increasingly bold in pushing boundaries over the years while sustaining just the right amount of tension to not get too ahead of itself. As the fusing of disparate subcultures come to fruition, this season is all about walking the line – whether it’s the integration of unconventional pairings or the masculinization of formerly none-male items.

This season, we’ve selected 5 menswear trends that we think best represent what’s being hyped in the LOOKBOOK community and what’s been seen on top influencers, tastemakers and fashion designers around the world.

Check out how our members have styled or reimagined our favorite trends for Spring 2014.

1. Mid Century Modern

Click the image above for more inspiration. Photo credit: Tim M.

Welcome to modern-day Don Draper. The dapper dude of the 50s is back, with a touch of dandy. The high-waist, casual collar metro look is not only posh and manly, but handles itself quite well with airs of confidence and charm.

Collections in Milan and Paris were heavily influenced by this style come runway season. While Bottega Veneta’s Tomas Maier kept things updated with painted-on details, Brioni’s Brendan Mullane channeled inspiration from the founders’ historic trip to London made over half a century ago. Lanvin, Prada, Carven, Michael Kors and Yohji Yamamoto presented looser, monochromatic versions.

Essentials of the mid century modern man include crisp button-downs, loose-fitting blazers, sweater vests, suspenders, Chelsea boots and penny loafers. You can accentuate this look with colorful pocket squares and bow ties (or tuck in the tail of your tie for a classic look). For a more relaxed feel, slip on a Bermuda short with a pair of espadrilles.

2. Sport Inspired Streetwear

Click the image above for more inspiration. Photo credit: Abdulqadir A.

One of the biggest influences penetrating men’s street fashion for 2014 is athleticism, particularly those catered to street and lifestyle-inspired sports like boarding, skating and biking – with a 90s leaning reference.

Designers like Givenchy, Kris Van Assche and James Long have re-established sportswear as a must-have for this season with leathers, slim fitting mesh tops and Lycra bottoms inspired by surf and skate. Skingraft and Paul Smith did some mixology on jerseys and bombers with leather and mesh while others, like Raf Simmons and Opening Ceremony, took a more artistic turn, printing bright colors and graphics on oversized tees and sweats. Staple sportswear brand Nike continues its covetable collaborations with streetwear-minded designers Liberty of London, Supreme and Pigalle.

Key pieces for this look include hockey jerseys, varsity and bomber jackets, Neoprene tees, joggers, sweatpants, snapbacks and kicks. Shorts over leggings, championed by the likes of Kanye and Alexander Wang, can be accomplished by keeping shorts (try mesh or Lycra) loose and long. The use of dark colors and monochrome helps keep the look strong and edgy.

3. Botanical Prints

Click the image above for more inspiration. Photo credit: Vini U.

Prints and patterns are huge for spring, with florals taking the lead in a brooding, moody sort of way. The rise of dark flowers took root last summer and are now seen everywhere – from high-end designer to high-street, Dries Van Noten to Topman. Details such as ribbing on cuffs and waistband offset the flourishes as the trend infuses itself with contemporary sportswear. With a hint of artistry, it’s become more botanical than tropical this season.

Raf Simons kept things abstract with pop art tulips, while designers like Prada, Marc Jacobs and River Island went moody Hawaiian in a kind of Aloha Noir, with Topman following suit. Gucci and Alexander McQueen experimented with clashed tailoring, embroidering black roses on striped blazers, while Dries Van Noten’s played to the tune of a refined garden with deep flower prints and rococo detailing.

A good floral can make for a strong statement of confidence and boldness. Framing amid a dark background modernizes it and integrating neutral shapes and colors help tone things down. Pair floral trousers with a plain crew knit, a foliaged blazer with a basic white tee, or toughen up a Hawaiian shirt with some raw denim jeans.

4. The Cuffed Pant

Click the image above for more inspiration. Photo credit: Marcel F.

Cuffed pants are set for a steady rise in 2014, looking distinctly more futuristic than previous incarnations. With strong influences from the likes of Kanye, Rick Ross, Drake and the industry’s current fixation on sports luxe and the slim sweatpant, it can be applied to nearly everything, from trousers and jeans to bermudas and joggers.

Brands like Topman and Publish offer ready-made cuffed or tapered pants in a myriad of colors, fabrics and patterns, from leather, corduroy, cargo, polka dot, snakeskin, chambray, khaki and plaid, to the classic pair of sweatpants.

The cuffed pant can be easily matched with a form fitted Henley and some low top sneakers, classed up with a nice oxford shirt and pair of Chelsea boots, or in-between with a textured knit over a tailored cotton shirt and minimal trainers. Slim and neat is the way to go with this trend.

5. The Man Bag

Click the image above for more inspiration. Photo credit: Mikko P.

Bags. They are big news in the world of menswear. Designers have extended their palette from traditional turn-of-the-millennium messengers into increasingly sophisticated options - seeking to not only provide the practicality of storing life’s essentials but to showcase a rugged yet modern accent to round out a look. The top bag styles for men this season are the briefcase, the folio, the backpack and the satchel.

For a tailored, sharp finish, the briefcase pairs nicely with buttoned-up attire. We’ve seen plenty of them in vintage, or from designers Jack Spade, Alex Folzi, Reiss and Ted Baker. The folio provides a similar clean-cut silhouette for lighter iPad-only days.

Backpacks and satchels are more versatile for everyday, having been spurred by recent technical and athletic trends. Killspencer is a mainstay for the stylish and functional, and Côte&Ciel for something edgier. Upscale Givenchy and Marc Jacobs are making their statement with geometric prints, while other designer offerings, like Chanel’s spray-painted SS ’14 rucksack and Kris Van Assche’s white croc pattern, aim for a more unique route.