Blue Ripped Skinny Jeans Grey Plaid Scarf Dark Brown Woven Leather Belt Black Windbreaker Black Sunglasses White Crew-neck T-shirt

What to wear with a windbreaker: If you're all about comfort dressing when it comes to your personal style, you'll love this on-trend combination of a windbreaker and blue destroyed slim jeans. We're loving this one, especially for springtime.

Light Blue Windbreaker White Crew-neck T-shirt Grey Jeans Olive Backpack

This combination of a windbreaker and grey jeans is the ideal balance between casual and dapper. Keep this ensemble ready to go come spring, and we guarantee you'll save a lot of time getting dressed on more than one occasion.

White Print Crew-neck T-shirt Black Windbreaker Black Hoodie Olive Backpack Charcoal Jeans

What to wear with a windbreaker: Pair a windbreaker with dark grey jeans for a trendy and easy going look. You can bet this getup is the answer to all of your transitional dressing problems.

White Crew-neck T-shirt Red Windbreaker Blue Jeans Tan Suede Desert Boots

If you're facing a fashion situation where comfort is prized, pair a windbreaker with blue jeans. Rock a pair of tan suede desert boots for a masculine aesthetic. A great illustration of transitional style, this outfit is perfect when warmer days are here.

White and Navy Horizontal Striped Crew-neck Sweater Mustard Chinos Brown Windbreaker Navy and White Boat Shoes

Windbreaker combination: A windbreaker and mustard chino pants is a smart combination to add to your styling repertoire. Navy and white boat shoes are a smart choice to round off the look. As you can see, this outfit is a really smart pick, especially for summer-to-fall weather, when the temps are dipping.

Navy Baseball Cap Olive Print Crew-neck T-shirt Navy Windbreaker Blue Denim Shorts Navy and White Print Plimsolls

What goes with a windbreaker: The versatility of a windbreaker and blue denim shorts makes them investment-worthy pieces. Consider navy and white print sneakers as the glue that will bring your look together. As this outfit proves, you can't think of a better pick for summer.

Yellow Windbreaker Black and White Gingham Dress Shirt Black Blazer Red Chinos

How to style a windbreaker: A windbreaker and red chinos is a nice combination to add to your casual repertoire. If you feel uninspired by your transitional weather fashion options, this look just might be the inspo you need.

Blue Crew-neck T-shirt Grey Suit Navy Windbreaker Navy Suede Slip-on Sneakers

Pairing a windbreaker and a grey suit will create a powerful and confident silhouette. Choose a pair of navy suede slip-on sneakers for a more relaxed feel. Seeing as fall is fast approaching, this look seems a smart choice for the transitional season.

Navy Windbreaker Blue Jeans Olive Crew-neck Sweater Charcoal Canvas Tote Bag Charcoal Leather Desert Boots

A windbreaker and blue jeans are both versatile essentials that will give your outfits a subtle modification. Add dark grey leather desert boots to your outfit for an instant style upgrade. When it comes to dressing for autumn, nothing beats a killer look that will keep you snug and looking your best.

White Horizontal Striped V-neck T-shirt Dark Brown Woven Leather Belt Blue Jeans Navy Canvas Plimsolls Grey Windbreaker

How to wear a windbreaker: A windbreaker and blue jeans are great staples that will integrate perfectly within your current looks. For shoes, rock a pair of navy canvas plimsolls. With the departure of snow come warmer afternoons and balmy nights and the need for a #{cool} look just like this one.

Brown Leather Messenger Bag Black Sunglasses Tan Long Sleeve Shirt Burgundy Chinos Charcoal Suede Derby Shoes Grey Windbreaker

Marry a windbreaker with oxblood chinos for a casual level of dress. Choose a pair of dark grey suede derby shoes to take things up a notch. We're loving how perfect this one is for transeasonal weather.

Light Violet Short Sleeve Shirt Olive Windbreaker Grey Sweatpants White Low Top Sneakers

Try pairing a windbreaker with grey track pants for a relaxed take on day-to-day wear. Round off with white low top sneakers and off you go looking great. Spring is a beautiful time of year and it calls for standout looks just like this one.

Navy Baseball Cap Navy Windbreaker Dark Green Camouflage Long Sleeve Shirt Black Jeans Black and White Low Top Sneakers Dark Green Camouflage Watch

What goes with a windbreaker: If you enjoy a more casual approach to dressing up, why not make a windbreaker and black jeans your outfit choice? Round off your getup with monochrome low top sneakers. When it comes to dressing for in-between weather, nothing beats a knockout look that transitions easily between seasons.

Black Windbreaker Red Plaid Baseball Cap Charcoal Sweatpants Black Athletic Shoes

For a comfortable-as-your-couch outfit, reach for a windbreaker and charcoal running pants. Dress down this getup with black athletic shoes. On not-so-chilly afternoons, rock a version of this summer-to-fall getup and look absolutely amazing.

White Windbreaker Light Blue Chinos Pink Gingham Belt White Woven Leather Derby Shoes Grey Horizontal Striped Long Sleeve Shirt

Look stylish yet practical in a windbreaker and light blue chinos. Why not introduce white woven leather derby shoes to the mix for an added touch of style? So so as you can see, it's a sharp, not to mention spring-ready, getup to have in your transeasonal rotation.

Black Windbreaker Black Canvas Duffle Bag Olive Camouflage Chinos Mint Athletic Shoes

A windbreaker and olive camo chinos are great staples that will integrate perfectly within your current looks. Feeling brave? Complete your look with mint athletic shoes. As the weather improves, it's time to shed those heavy winter #['clothes', 'layers', 'gear'].sample} and choose an ensemble that's lighter, like this one here.

Grey Camouflage Bomber Jacket Olive Sweatpants Olive Windbreaker Black Sunglasses Tan Suede Casual Boots

What to wear with a windbreaker: Marry a windbreaker with army green sweatpants for a laid-back yet fashion-forward outfit. Let's make a bit more effort now and opt for a pair of tan suede casual boots. This outfit is an excellent pick if you're planning a stylish summer-to-fall transition outfit.

Black Sunglasses White Dress Shirt Navy and White Horizontal Striped Crew-neck Sweater Olive Skinny Jeans Dark Brown Leather Casual Boots Navy and White Windbreaker

Consider teaming a windbreaker with olive skinny jeans to bring out the stylish in you. A pair of dark brown leather casual boots adds more polish to your overall look.  An ensemble like this makes it easy to embrace unpredictable transeasonal weather.