Black Crew-neck Sweater Red Windbreaker Grey Long Sleeve Shirt Black Jeans Grey Suede Low Top Sneakers

If it's comfort and practicality that you're seeking in an outfit, reach for a windbreaker and black jeans. As for the shoes, rock a pair of grey suede low top sneakers. It's is an obvious idea when it comes to a cool outfit that will take you from summer to fall.

Dark Brown Leather Casual Boots Blue Jeans Beige Wool Gloves Tobacco Turtleneck Dark Green Quilted Gilet Red Windbreaker

This pairing of a windbreaker and blue jeans combines comfort and practicality and allows you to keep it simple yet current. A pair of dark brown leather casual boots will add some real flair to this ensemble. On not-so-bone-chilling afternoons, work this summer-to-fall ensemble and look absolutely amazing.

Black Sunglasses Black Turtleneck Black Baseball Cap Orange Windbreaker Grey Leather Briefcase Grey Plaid Overcoat Black Chinos Grey Athletic Shoes

Nail off-duty dressing with this pairing of a windbreaker and black chinos. A pair of grey athletic shoes ads edginess to a classic style. A cool summer-to-fall ensemble like this one makes it very easy to embrace the new season.

Navy Windbreaker Black Leather Gloves Blue Beanie Navy Sunglasses Navy Jeans Black Low Top Sneakers

This combination of a windbreaker and navy jeans is super easy to achieve and so comfortable to sport all day long as well! A pair of black low top sneakers looks proper here. A look like this makes it easy to embrace unpredictable transeasonal weather.

White and Red Print Crew-neck T-shirt Dark Green Windbreaker Gold Watch Black Leather Belt Blue Jeans White Leather Low Top Sneakers

Consider teaming a windbreaker with blue jeans to show off your styling savvy. Round off this ensemble with white leather low top sneakers. When spring is in full effect, you'll appreciate how great this ensemble is for transitional weather.

Black Print Baseball Cap Red Hoodie Black Windbreaker Light Blue Ripped Skinny Jeans White Canvas Low Top Sneakers

A windbreaker and light blue ripped skinny jeans are a great outfit formula to have in your arsenal. Bump up the cool of your look by completing it with white canvas low top sneakers. This one will play especially nice when warmer days are here.

White Crew-neck T-shirt Black Leather Backpack Black Sweatshirt Tobacco Windbreaker Navy Skinny Jeans White Canvas Low Top Sneakers

Wear a windbreaker and navy skinny jeans for a casual-cool vibe. When it comes to footwear, this getup pairs nicely with white canvas low top sneakers. This one is an exciting pick if you're on the lookout for a killer summer-to-fall look.

White Canvas Low Top Sneakers Grey Shorts Navy Windbreaker Black Canvas Messenger Bag White and Red and Navy Plaid Long Sleeve Shirt

A windbreaker and grey shorts is a nice pairing worth integrating into your wardrobe. A pair of white canvas low top sneakers looks very appropriate here. Seeing as it's roasting hot outside, this combination appears ideal and entirely summer-appropriate.

Olive Windbreaker Beige Shorts White and Black Horizontal Striped Socks White Leather Low Top Sneakers

A windbreaker and beige shorts feel perfectly suited for weekend activities of all kinds. Finish off this outfit with white leather low top sneakers. We love that this look is great when sunny days set in.

White and Red Print Crew-neck T-shirt Black Windbreaker Black Cargo Pants Black Athletic Shoes

If you enjoy a more relaxed approach to dressing up, why not consider teaming a windbreaker with black cargo pants? Black athletic shoes will deliver a casual vibe to your look. These picks will keep you warm and stylish in unpredictable fall weather.

Black Print Baseball Cap Yellow Windbreaker Black Wool Gloves Black Skinny Jeans Black Leather Derby Shoes

Make a windbreaker and black skinny jeans your outfit choice for a comfy-casual look. And if you want to instantly up the style ante of your look with one piece, add black leather derby shoes to the equation. We're loving how perfect this ensemble is come fall.

Light Blue Vertical Striped Long Sleeve Shirt White and Red and Navy Windbreaker Black Print Baseball Cap Black Sweatpants White Socks Beige Athletic Shoes

If you're a fan of relaxed dressing when it comes to fashion, you'll love this simple pairing of a windbreaker and black sweatpants. For a more relaxed take, opt for a pair of beige athletic shoes. As the weather is getting warmer, it's time to shed those bulky winter gear and opt for something lighter, like this ensemble here.

Red Hoodie Navy Windbreaker Black Jeans Brown Athletic Shoes

A resounding yes to this combination of a windbreaker and black jeans! Brown athletic shoes are the right shoes here to get you noticed. You can bet this ensemble is the answer to all of your transeasonal style struggles.

White Horizontal Striped Crew-neck T-shirt Orange Windbreaker Black Chinos Grey Suede Low Top Sneakers Grey Socks

Stylish yet comfortable, this outfit features a windbreaker and black chinos. A pair of grey suede low top sneakers looks proper here. This one will play especially well when warmer days are here.

Yellow Linen Long Sleeve Shirt Orange Windbreaker Tan Shorts White Low Top Sneakers

A windbreaker and tan shorts is a good pairing to carry you throughout the day. White low top sneakers are a nice choice to finish off the look. This ensemble is truly a lesson in how to dress for warm summer weather.

White Horizontal Striped Crew-neck T-shirt Green-Yellow Windbreaker Dark Green Chinos Black Low Top Sneakers

Busy days call for a simple yet stylish outfit, such as a windbreaker and dark green chinos. Round off this ensemble with black low top sneakers. Keep this outfit in your front hall closet come warmer days, and rest assured, you'll save a ton of time getting ready on more than one occasion.

White and Black Horizontal Striped Crew-neck T-shirt White Windbreaker Olive Chinos Dark Green Low Top Sneakers

A windbreaker and olive chinos are both versatile essentials that will give your outfits a subtle modification. A pair of dark green low top sneakers looks very fitting here. A perfect example of transeasonal fashion, this ensemble is great when spring arrives.

Orange Windbreaker Grey Crew-neck T-shirt Black Shorts Black Athletic Shoes

If you're facing a fashion situation where comfort is prized, rock a windbreaker with black shorts. Make black athletic shoes your footwear choice for a more relaxed feel. No doubt, it's easier to work through a baking hot afternoon in a breezy getup such as this one.